BIOCHEM PRELIM REVIEWER Flashcards by Qian

CELL

was the first person to use the term “cell”

Robert Hooke

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He referred to the small
empty chambers in the structure of cork as cells.

Robert Hooke

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concluded that all plant and animal
tissues were composed of cells

Matthias Schleiden and Theodor Schwann

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proposed the theory of biogenesis where cells only arise from preexisting cells.

Rudolf Virchow

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is the basic structural and functional unit of living organisms

cell

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explores molecular
mechanisms of normal cellular processes
as well as diseases

Biochemistry

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All higher living organisms including _______ are made up of cells

humans

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Two major classes:

Prokaryotes
Eukaryotes

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DNA is found in the nucleus of the cell

EUKARYOTES

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DNA is not enclosed within the
membrane

PROKARYOTES

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Contain membrane-bound
organelles which include mitochondria, endoplasmic
reticulum, and Golgi complex

EUKARYOTES

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Lack membrane-enclosed organelles

PROKARYOTES

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Cell division involves mitosis.

EUKARYOTES

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Usually divide by binary fission.

PROKARYOTES

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Water accounts for about _______ of the weight of the cell.

70-75%

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Organic compounds accounts for _________ of the cell weight.

25-30%

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They are nucleic acids, proteins, polysaccharides
(carbohydrates) and lipids.

MOLECULAR COMPOSITION OF CELL

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account for the rest of the cell weight.

Inorganic compounds

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have a membrane-bound nucleus and a number of other
membrane-bound subcellular (internal) organelles, each of which has a specific
function.

EUKARYOTIC CELL

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Structure: Phospholipid bilayer
containing cholesterol and proteins and
some carbohydrates; forms a selectively
permeable boundary of the cell.

PLASMA MEMBRANE

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Functions: Acts as a physical barrier to
enclose cell contents; regulates material
movement into and out of the cell; functions in cell communication

PLASMA MEMBRANE

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Function: It contains the DNA that
serves as the genetic material for
directing protein synthesis.

NUCLEUS

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Structure: It is enclosed within a
double membrane called

nuclear
envelope

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Structure: It is enclosed within a
double membrane called nuclear
envelope; contains

nucleolus

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It consists of RNA and proteins which functions in ribosomal unit assembly

Nucleolus

It surrounds the chromatin and the nucleoli.

Nucleoplasm

* Structure: This can be seen between the plasma membrane and the nucleus where the other cellular elements are embedded

CYTOPLASM

are membrane-bound structures which carry out specific metabolic activities of the cell.

Organelles

provides support for organelles and serves as the viscous fluid medium.

Cytosol

Function: It is responsible for various cellular processes.

CYTOPLASM

Structure: Double-membrane-bound organelles containing a circular strand of DNA

MITOCHONDRIA

is highly permeable to small molecules, due to the presence of a pore-forming protein called porin.

Outer membrane

Outer membrane is highly permeable to small molecules, due to the presence of a pore-forming protein called

porin

contains many proteins that participate in oxidative phosphorylation.

Intermembrane

has multiple folds projecting inwards, called cristae.

Inner membrane

Inner membrane has multiple folds projecting inwards, called

cristae

Function: It is responsible for the production of energy in the form of ATP

MITOCHONDRIA

Structure: Spherical shaped membrane bound organelles formed from the golgi apparatus; contain digestive enzymes

LYSOSOMES

The fluid inside lysosomes is much more acidic, at about _______________ than the normal pH of about 7.0– 7.3

pH 4.8

Function: Digest microbes or materials by the cell

LYSOSOMES

Structure: Extensive interconnected membrane network that varies in shape; ribosomes attached on the cytoplasmic surfaces

Rough endoplasmic reticulum

are involved in the protein synthesis

Ribosomes

Functions: Modifies, transports, and stores proteins produces by attached ribosomes

Rough endoplasmic reticulum

Structure: Extensive interconnected membrane network lacking ribosomes

Smooth endoplasmic reticulum

Structure: Series of several elongated, flattened saclike membranous structures.

GOLGI APPARATUS

Functions: Modifies, packages, and sorts materials, that arrive from the endoplasmic reticulum in transport vesicles

GOLGI APPARATUS

transport cellular material. Mature vesicles are called secretory vesicles.

Vesicles

Vesicles transport cellular material. Mature vesicles are called

secretory vesicles

Structure: smaller, spherical membrane bound organelles formed from the endoplasmic reticulum.

PEROXISOMES

Functions: Detoxify specific harmful substances either produced by the cell or taken into the cell

PEROXISOMES

Structure: Organized network of protein filaments

CYTOSKELETON

Function: Maintains integral structural support and organization of cells

CYTOSKELETON

maintain cell shape.

Microfilaments

give mechanical support to structures like nucleus and plasma membrane.

Intermediate filaments

provides structural support.

Microtubules

Prokaryotes

(Eubacteria and Archaebacteria)

are the most abundant organisms on earth.

Prokaryotes (Eubacteria and Archaebacteria)

does not contain a membranebound nucleus.

prokaryotic cell

is surrounded by a plasma membrane.

prokaryotic cell

has no subcellular organelles, only infoldings of the plasma membrane called mesosomes

cell

is condensed within the cytosol to form the nucleoid.

deoxyribonucleic acid (DNA)

have tail-like flagella.

prokaryotes

# Passive Transport Process is the movement of a substance from an area of its higher concentration to an area of its lower concentration.

Diffusion

# Passive Transport Process is the type of diffusion of dissolved solutes through the plasma membrane

Simple diffusion

# Passive Transport Process is the type of diffusion that requires a protein carrier.

Facilitated Diffusion

# Passive Transport Process is the diffusion of water point across a selectively permeable membrane

Osmosis

This type of cell membrane transport uses energy (ATP) provided by the cell.

Active Transport Process

# Active Transport Process For example, cell has low intracellular sodium; but concentration of potassium inside the cell is very high. This is maintained by the

sodium– potassium activated ATPase

# Active Transport Process For example, cell has low intracellular sodium; but concentration of potassium inside the cell is very high. This is maintained by the sodium– potassium activated ATPase, generally called as

sodium pump

# Active Transport Process refers to bulk movement of substance out of the cell by fusion of secretory vesicles with the plasma membrane.

Exocytosis

# Active Transport Process refers to bulk movement of substance into the cells by vesicles forming at the plasma membrane.

Endocytosis

It is the longer phase of the cell cycle where the cell is active and preparing for cell division.

Interphase

Cells arise from the division of other cells.

Cell Division

consists of four stages-prophase, metaphase, anaphase, and telophase. The result is two daughter nuclei, each identical to the mother nucleus.

Mitosis

each chromosome consists of two chromatids joined at the centromere.

Prophase

chromosomes align at the center of the cell

Metaphase

chromatids separate at the centromere and migrate to opposite poles.

Anaphase

two new nuclei assume their normal structure, and cell division is completed, producing two new daughter cells.

Telophase

is a combination of true and a colloidal solution since some of its components are insoluble while others are soluble in its water medium.

cell (protoplasm)

colloidal properties of the cell

Filterability Negligible Osmotic Pressure Tyndall Phenomenon Brownian Movement Electrical Charges

Particles of colloidal solution can pass through ordinary filter paper but not through parchment membrane.

Filterability

Particles are comparatively small therefore they have negligible osmotic pressure

Negligible Osmotic Pressure

Colloidal solution possesses Tyndall Effect

Tyndall Phenomenon

Suspended particles of a colloidal solution are observed to be in continuous, rapid vibratory motion.

Brownian Movement

Colloidal particles are electrically charged, the charged being distributed over the surface of the entire particle

Electrical Charges

Molecules in the interior of a homogenous liquid are attached in all directions by surrounding molecules so they move freely in all direction while surface molecules are attracted more towards the center of the liquid making the surface molecules more compact. The force by which the surface molecule are held is called the

Surface tension

Whenever a semi-permeable membrane separates two solutions of unequal concentrations, the fluid tends to flow from the side of low osmotic pressure to that of higher osmotic pressure until an osmotic equilibrium is established.

Osmosis

the cell tends to shrink

hypertonic

# CELL medium, the cell tends to swell.

hypotonic

# CELL Interpenetration of molecules between two substances occurs whenever the solute distributes itself uniformly into the solvent. Small molecules and ions move faster than macromolecules. The rate of diffusion of substances is dependent on the molecular size, weight, shape and the concentration gradient.

Diffusion

# CELL When a semi-permeable membrane allows the passage of the crystalloids but not the colloids, the rate of dialysis depends on the size of the pores, temperature, electrical charge, area of dialyzer, and the relative concentration on the two sides of the membrane.

Dialysis

# CELL is an essential substance for plant and animal growth. Without water, there would be no life on earth.

water

# CELL is essential to life and is in solvent water that the chemical reactions of biological processes evolved.

water

# CELL is the major component of the cell,

water

# CELL water is the major component of the cell, making around __________ of its weight and inert space filler in living organism.

70 to 90%

# CELL Due to its highly reactive and unusual properties and its ionization products

H+ and OH-

# CELL is an important factor in modifying structures of biomolecules such as nucleic acids, carbohydrates, proteins, lipids, enzymes, and other cell components

water

# CELL General Properties of Water

1. Chemically pure water is colorless, odorless and tasteless. 2. Has a higher boiling point and osmotic pressure. 3. High specific heat. 4. High latent heat of vaporization. 5. High surface tension. 6. Had the capacity to dissipate heat to its environment.

# CELL Water is an excellent solvent for ionic compounds because of the attraction between the ionic components of the molecules and the water dipoles is sufficient to overcome the attraction between the ions themselves. Non-ionic polar compounds such as sugars, alcohols, aldehydes and ketones are also very soluble in water. Their polar functional group [OH] readily hydrogen bonds with water molecules, dispersing the compounds among the water molecules. Other substances dispersed by water are those hydrophobic group known as amphipathic molecules such as salts and fat acids and are called micelles. Micelle formation is important for an understanding of organized biological system among amphipathic compounds such as proteins, phospholipids and nucleic acids.

A universal solvent

# CELL Water is an irregular tetrahedron with oxygen at its center. Two hydrogen are bonded with oxygen forming 105o a slightly skewed tetrahedron. Because of this structure electrical charge is not distributed uniformly about the water molecule. The oxygen side is partially negative because of the relatively rich in electrons and the two hydrogen forming a region of local positive charge. The unequal distribution of charges with in a molecule is term “dipole” such as in water

An Electron Dipole

# CELL Colligative properties such as freezing point and boiling point, vapor pressure and aromatic pressure are altered by dissolved solutes. Colligative properties depend only in the number of solute molecules per unit volume of solvent and independent of their chemical structure. Dissolved solutes disturbed hydrogen bonding in water molecules, thus reducing its effect as a solvent.

Altered by Solutes

# CELL A system that can resist a change in pH upon the addition of either acid or base is called a buffer. Solutions of weak acids and their conjugate bases and on weak bases and their conjugate acids exhibit buffering. Functional groups such as carboxyl group, amino group and phosphate esters are functional groups of are weak acids or bases that many biomolecules possess. In humans, the main extra cellular buffering system is the bicarbonate system (H2CO3/ HCO3- buffer pair), and the principal intra cellular system involves the second dissociation of phosphoric acid (H2PO4-/ HPO42-).

Physiological Buffer System

# CELL Vital to the normal functioning of some enzymes and for the maintenance of functional conformation of proteins, nucleic acids, and carbohydrates

Inorganic ions

# Review of Functional Groups Study of hydrocarbons (only carbon and hydrogen atoms) and their various derivatives.

Organic chemistry

Study of all substances other than hydrocarbons and their derivatives.

Inorganic chemistry

always makes total of 4 Bonds

C-atom

The sharing of ___________ requires the formation of four covalent bonds which are represented by four lines

four valance electrons

are groups of atoms in organic molecules that are responsible for the characteristics, chemical reactions of those molecules.

Functional Groups

that contain the same functional group in their structure can be expected to react in similar ways.

Simple molecules

may contain more than one functional group within their structure

More complicated chemical molecules

Hydrocarbons

Alkanes Alkenes Alkynes Arenes

Alkanes

Hydrocarbons

Alkenes

Hydrocarbons

Alkynes

Hydrocarbons

Arenes

Hydrocarbons

Alkanes: General Formula

Alkenes: General Formula

RR'C=CR"R'"

Alkynes: General Formula

RC=CR'

Arenes: General Formula

ArH

Alkanes: Common Name

ethane

Alkenes: Common Name

ethylene (ethene)

Alkynes: Common Name

acetylene (ethyne)

Arenes: Common Name

benzene

Alkanes: Common Suffix/Prefix (Systematic)

-ane

Alkenes: Common Suffix/Prefix (Systematic)

-ene

Alkynes: Common Suffix/Prefix (Systematic)

(-yne)

Arenes: Common Suffix/Prefix (Systematic)

-ene

Halogen-Containing Compounds

Alkyl Halides Aryl Halides

Halogen-Containing Compounds

Alkyl Halides

Halogen-Containing Compounds

Aryl Halides

Alkyl Halides: General Formula

Aryl Halides: General Formula

ArX

Alkyl Halides: Common Name (Systematic Name)

ethyl cloride (chloroethane)

Aryl Halides: Common Name (Systematic Name)

chlorobenzene

Alkyl Halides: Common Suffix/Prefix (Systematic)

halide (halo-)

Aryl Halides: Common Suffix/Prefix (Systematic)

halo-

Oxygen-Containing Compounds

Alcohols Phenols Ethers Aldehydes Ketones Carboxylic acids

Phenols

Oxygen-Containing Compounds

Ethers

Oxygen-Containing Compounds

Aldehydes

Oxygen-Containing Compounds

Ketones

Oxygen-Containing Compounds

Carboxylic acids

Oxygen-Containing Compounds

Alcohols: General Formula

ROH^

Phenols: General Formula

ArOH^b

Ethers: General Formula

ROR^r

Aldehydes: General Formula

RCHO

Ketones: General Formula

RR'C=O

Carboxylic acids: General Formula

RCO^2H

Alcohols: Common Name (Systematic Name)

ethyl alcohol (ethanol)

Phenols: Common Name (Systematic Name)

phenol

Ethers: Common Name (Systematic Name)

diethyl ether

Aldehydes: Common Name (Systematic Name)

acetaldehyde (ethanal)

Ketones: Common Name (Systematic Name)

acetone (2-propane)

Carboxylic acids: Common Name (Systematic Name)

acetic acid (ethanoic acid)

Alcohols: Common Suffix/Prefix (Systematic)

-ol

Phenols: Common Suffix/Prefix (Systematic)

-ol

Ethers: Common Suffix/Prefix (Systematic)

ether

Aldehydes: Common Suffix/Prefix (Systematic)

-aldehyde (-al)

Carboxylic acids: Common Suffix/Prefix (Systematic)

-ic acid (-oic acid)

Ketones: Common Suffix/Prefix (Systematic)

-one

Carboxylic Acid Derivatives

Ester Amides

Ester

Carboxylic Acid Derivatives

Amides

Carboxylic Acid Derivatives

Ester: General Formula

RCO^2R^F

Amides: General Formula

RCONHR^r

Ester: Common Name (Systematic Name)

methyl acetate (methyl ethanoate)

Amides: Common Name (Systematic Name)

N-methylacetamide

Ester: Common Suffix/Prefix (Systematic)

-ate (-oate)

Amides: Common Suffix/Prefix (Systematic)

-amide

Nitrogen-Containing Compounds

Amines Nitriles Nitro compounds

Amines

Nitrogen-Containing Compounds

Nitriles

Nitrogen-Containing Compounds

Nitro compounds

Nitrogen-Containing Compounds

Amines: General Formula

RNH^2r RNHR^F^F RNR^r R"

Nitriles: General Formula

RC triple bond N

Nitro compounds: General Formula

ArNO^2^

Amines: Common Name (Systematic Name)

ethylamine

Nitriles: Common Name (Systematic Name)

acetonitrile

Nitro compounds: Common Name (Systematic Name)

nitrobenzene

Amines: Common Suffix/Prefix (Systematic)

-amine

Nitriles: Common Suffix/Prefix (Systematic)

-nitrile

Nitro compounds: Common Suffix/Prefix (Systematic)

nitro-

is the study of the chemical substances found in living organisms and the chemical interactions of these substances with each other

Biochemistry

is a chemical substance found within a living organism

biochemical substance

Two types of biochemical substances

bioinorganic substances and bioorganic substances

carbohydrates, lipids, proteins, and nucleic acids

Bioorganic substances

water and inorganic salts.

Bioinorganic substances

As isolated compounds, bioinorganic and bioorganic substances have no life in and of themselves. Yet when these substances are gathered together in a cell, their chemical interactions are able to

sustain life

It is estimated that more than half of all______ are found in the carbohydrate materials of plants

organic carbon atoms

uses for carbohydrates of the plant kingdom extend beyond food.

Human

in the form of cotton and linen are used as clothing.

Carbohydrates

in the form of wood are used for shelter and heating and in making paper.

Carbohydrates

75% of dry plant material

Photosynthesis

structural element

Cellulose

energy reservoir

Starch/glycogen

small amount in human body

Starch/glycogen

are source of carbohydrates

Plant products

average human diet contains

2/3 of carbohydrates

Most of the matter in plants, except ___________ is carbohydrate material.

water

provides energy

Carbohydrate oxidation

in the form of glycogen, provides a short-term energy reserve

Carbohydrate storage

Carbohydrates supply ______ for the synthesis of other biochemical substances (proteins, lipids, and nucleic acids)

carbon atoms

Carbohydrates form part of the

structural framework of DNA and RNA molecules

are structural components of cell membranes

Carbohydrates linked to lipids

function in a variety of cell–cell and cell–molecule recognition processes

Carbohydrates linked to proteins

Photosynthesis * Simpler Formula:

CnH2nOn or Cn(H2O)n (hydrates of C) – n= number of atoms

Carbohydrates are _________ that produce such substances upon hydrolysis

polyhydroxy aldehydes or ketones or compounds

Contain single polyhydroxy aldehyde or ketone unit

Monosaccharide

They can’t be broken down into simpler substances by hydrolysis (reaction with water) reactions

Monosaccharide

# Monosaccharide Contains _________ atoms

3-7 C

# Monosaccharide carbon species are more common

5 and 6 carbon species

# Monosaccharide Water soluble

white crystalline solids

Contains ~2-10 monosaccharide units - covalently bonded to each other

Oligosaccharides

(contain 2 monosaccharide units) more common - crystalline water soluble substances

Disaccharides

Table sugar

sucrose

milk sugar

lactose

- are common disaccharides

sucrose & lactose

Upon hydrolysis they produce monosaccharide

Oligosaccharides

In human body associated with proteins and lipids for structural and regulatory functions

Oligosaccharides

Contains many monosaccharide units covalently bonded

Polysaccharides

# Polysaccharides May contain 100s of 1000s of monosaccharide units

Polymers

# Polysaccharides Paper, cotton, wood

Cellulose

# Polysaccharides Bread, pasta, potatoes, rice, corn, beans, peas, etc

Starch

Classification of Carbohydrates

Monosaccharide Oligosaccharides Polysaccharides

# Chirality: Handedness in Molecules Most monosaccharides exist in two forms

a “left handed” and “right handed” form

# Chirality: Handedness in Molecules Two types of objects

Superimposible on their mirror images Non-superimposible on their mirror images

images that coincide at all points when the images are laid upon each other -- a dinner plate with no design features -

Superimposible on their mirror images or Achiral

# Chirality: Handedness in Molecules Non-superimposible on their mirror images

Chiral (handedness)

C atom attached to 4 different groups

Chiral Center

# Chirality: Handedness in Molecules Best way to visualize - look at all C atoms and see if there are

at least two H atoms then that can’t be a chiral center

# Chirality: Handedness in Molecules are worth looking at for their chirality

C atoms with less than one H atoms

# Chirality: Handedness in Molecules Almost all monosaccharides are

right handed

# Chirality: Handedness in Molecules Amino acids are almost always

left handed

# Chirality: Handedness in Molecules Right handed hormone epinephrine is 20 times

more active than left handed form

are isomers that have the same molecular and structural formulas but differ in the orientation of atoms in space.

Stereoisomers

# Stereoisomerism: Enantiomers and Diasterioisomers Two types Stereoisomers

Enantiomers & Diastereomers

# Stereoisomerism: Enantiomers and Diasterioisomers are stereoisomers whose molecules are nonsuperimposable mirror images of each other. Molecules with chiral center.

Enantiomers

# Stereoisomerism: Enantiomers and Diasterioisomers are stereoisomers whose molecules are not mirror images of each other.

Diastereomers

# Designating Handedness Using Fischer Projection Formulas a method for giving molecular chirality specifications in two dimensions

Fischer projection formulas

# Designating Handedness Using Fischer Projection Formulas is a two-dimensional structural notation for showing the spatial arrangement of groups about chiral centers in molecules.

Fischer projection formula

# Designating Handedness Using Fischer Projection Formulas In a Fischer projection formula a __________is represented as the intersection of vertical and horizontal lines

chiral center (Carbon)

# Designating Handedness Using Fischer Projection Formulas Functional groups of high priority will be written at top

Fischer Project Formulas

# Designating Handedness Using Fischer Projection Formulas used to designate the handedness of glyceraldehyde enantiomers

D and L system

# Designating Handedness Using Fischer Projection Formulas The four groups attached to the atom at the chiral center assume a tetrahedral geometry and it is governed by the following conventions

Tetrahedral Arrangements

# Designating Handedness Using Fischer Projection Formulas: Tetrahedral Ar from the chiral center represent bonds to groups directed into the printed page. ## Footnote Tetrahedral Arrangements

Vertical lines ## Footnote Tetrahedral Arrangements

# Designating Handedness Using Fischer Projection Formulas: Tetrahedral Ar from the chiral center represent bonds to groups directed out of the printed page ## Footnote Tetrahedral Arrangements

Horizontal lines ## Footnote Tetrahedral Arrangements

# Designating Handedness Using Fischer Projection Formulas used to designate the handedness of glyceraldehyde enantiomers

D and L system

# Designating Handedness Using Fischer Projection Formulas D-Glyceroldehyde

D-Glyceroldehyde (-OH on right side)

L-Glyceroldehyde

L-Glyceroldehyde (-OH on left side)

# Designating Handedness Using Fischer Projection Formula a monosaccharide with four carbons and two chiral

2,3,4-trihydroxybutanal

# Designating Handedness Using Fischer Projection Formu used to designate the handedness of glyceraldehyde enantiomers can be extended to other monosaccharides with more than one chiral center

D,L system

# Designating Handedness Using Fischer Projection Formula is numbered starting at the carbonyl group end of the molecule, and the highest-numbered chiral center is used to determine D or L configuration

carbon chain

# Designating Handedness Using Fischer Projection Formulas are diastereomers whose molecules differ only in the configuration at one chiral

Epimers

# Properties of Enantiomer also differ in most chemical and physical properties. They also have different boiling points and freezing points

Diastereomers

# Properties of Enantiomer Two differences of Enantiomers ## Footnote Constitutional Isomers and Diastereom

1. Their interaction with plane polarized light 2. Their interaction with other chiral substan

# Properties of Enantiomer Move in all direct ## Footnote Interaction of Enantiomers with Plane-Polarized Light

Ordinary Light

# Properties of Enantiomers move only in one ## Footnote Interaction of Enantiomers with Plane-Polarized L

Plane polarized light

# Properties of Enantiomer to same extent but in opposite direction ## Footnote Interaction of Enantiomers with Plane-Polarized Light

Same concentration of two enantiomers rotate light

# Properties of Enantiomer is rotated clockwise * (to right) or counterclockwise (to left) when passed through enantiomers Direction and extent of rotation will * depend upon the enantiome ## Footnote Interaction of Enantiomers with Plane-Polarized Lig

Plane polarized light

are optically active: Compounds that rotate plane polarized light ## Footnote Dextrorotary and Levorotatory Compound

Enantiomers

# Properties of Enantiomers Chiral compound that rotates light towards right (clockwise; +)

Dextrorotatory

# Properties of Enantiomers Chiral compound that rotates light towards left (counterclockwise; -)

Levorotatory

# Properties of Enantiomers There is no correlation between ## Footnote Dextrorotary and Levorotatory Compounds

D, L and +, -

# Properties of Enantiomers you need to look at the structure ## Footnote Dextrorotary and Levorotatory Compound

D and L

# Properties of Enantiomers are determined by using a polarimeter ## Footnote Dextrorotary and Levorotatory Compounds

+ and -

# Properties of Enantiomers react differently with other chiral molecules ## Footnote Interactions Between Chiral Compounds

Two members of enantiomer pair (chiral)

# Properties of Enantiomers have same solubility in achiral solvents like ethanol and have different solubility in chiral solvent like D-2-butanol ## Footnote Interactions Between Chiral Compounds

Enantiomeric pairs

# Properties of Enantiomers have same boiling points, melting points and densities - all these are dependent upon intermolecular forces and chirality doesn’t depend on them ## Footnote Interactions Between Chiral Compounds

Enantiomers

# Properties of Enantiomers : Body response to ## Footnote Interactions Between Chiral Compounds

to D form of hormone

# Properties of Enantiomers epinephrine is 20 times greater than its ## Footnote Interactions Between Chiral Compounds

L isomer

# Classification of Monosaccharides 3 carbon atoms

Triose

# Classification of Monosaccharides 4 carbon atoms

Tetrose

5 carbon atoms

Pentoses

# Classification of Monosaccharides 6 carbon atoms

Hexoses

# Classification of Monosaccharides Monosaccharides with one aldehyde group

Aldoses

# Classification of Monosaccharides Monosaccharides with one ketone group

Ketoses

# Classification of Monosaccharides Most Common Monosaccharides ## Footnote Most Common Monosaccharides

Aldohexose Ketohexose

# Classification of Monosaccharides Monosaccharide with aldehyde group and 6 C atoms – D-glucose ## Footnote Most Common Monosaccharides

Aldohexose

# Classification of Monosaccharides Monosaccharide with aldehyde group and 6 C atoms – D-fructose ## Footnote Most Common Monosaccharides

Ketohexose

# Biochemically Important Monosaccharides also named grape sugar, dextrose and blood sugar (70 - 100 mg/100 mL of blood) ## Footnote Glucose and Fructose

Grape fruit good source of glucose (20 - 30% by mass)

# Biochemically Important Monosaccharides Most abundant in nature

Glucose

# Biochemically Important Monosaccharides Nutritionally most important

Glucose

# Biochemically Important Monosaccharides Six membered cyclic form

Glucose

# Biochemically Important Monosaccharides Ketohexose

Fructose

# Biochemically Important Monosaccharides Sweetest tasting of all sugars

Fructose

# Biochemically Important Monosaccharides Found in many fruits and in honey

Fructose

# Biochemically Important Monosaccharides Good dietary sugar-- due to higher sweetness

Fructose

# Biochemically Important Monosaccharides Five membered cyclic form

Fructose

Biochemically Important Monosaccharides

Glucose and Fructose Galactose and Ribose

# Biochemically Important Monosaccharides Milk sugar

Galactose

# Biochemically Important Monosaccharides synthesize in human

Galactose

# Biochemically Important Monosaccharides Also called brain sugar-- part of brain and nerve tissue

Galactose

# Biochemically Important Monosaccharides Used to differentiate between blood types

Galactose

# Biochemically Important Monosaccharides Six membered cyclic form

Galactose

# Biochemically Important Monosaccharides Part of RNA

Ribose

# Biochemically Important Monosaccharides Part of ATP

Ribose

# Biochemically Important Monosaccharides Part of DNA

Ribose

# Biochemically Important Monosaccharides Five membered cyclic form

Ribose

# Cyclic Forms of Monosaccharides Dominant form of monosaccharides with 5 or more C atoms is ## Footnote Cyclic Hemiacetal Forms of D-Glucose

cyclic

# Cyclic Forms of Monosaccharides are in equilibrium with open chain form ## Footnote Cyclic Hemiacetal Forms of D-Glucose

cyclic forms

# Cyclic Forms of Monosaccharides are formed by the reaction of carbonyl group (C=O) with hydroxyl (-OH) group on carbon 5 ## Footnote Cyclic Hemiacetal Forms of D-Glucose

Cyclic forms

# Cyclic Forms of Monosaccharides 2 forms of D-glucose ## Footnote Cyclic Hemiacetal Forms of D-Glucose

Alpha-form Beta-form

# Cyclic Forms of Monosaccharides OH of C1 and CH2OH of C5 are on opposite sides ## Footnote Cyclic Hemiacetal Forms of D-Glucose

Alpha-form

# Cyclic Forms of Monosaccharides -OH of C1 and CH2OH of C5 are on same sides ## Footnote Cyclic Hemiacetal Forms of D-Glucose

Beta-form

# Cyclic Forms of Monosaccharides Intramolecular cyclic hemiacetal formation and the equilibrium between various forms are

not restricted to glucose

# Cyclic Forms of Monosaccharides All aldoses with five or more carbon atoms establish similar _______ but with different percentages of the alpha, beta, and open-chain forms.

equilibria

# Cyclic Forms of Monosaccharides Fructose and other ketoses with a sufficient number of carbon atoms also

cyclize

# Cyclic Forms of Monosaccharides A cyclic monosaccharide containing a six-atom ring is called a ## Footnote Pyranose and Furanose

pyranose

# Cyclic Forms of Monosaccharides one containing a five-atom ring is called ## Footnote Pyranose and Furanose

**furanose** because their ring structures resemble the ring structures in the cyclic ethers pyran and furan respectively

Cyclic Forms of Monosaccharides

Pyranose and Furanose

is a two-dimensional structural notation that specifies the three-dimensional structure of a cyclic form of a monosaccharide.

Haworth projection formula

# Haworth Projection Formulas s determined by the position of the — OH group on C1 relative to the CH2OH group that determines D or L series.

Alpha or Beta configuration

# Haworth Projection Formulas both of these groups point in the same direction

Beta configuration

# Haworth Projection Formulas the two groups point in opposite directions

Alpha configuration

# Haworth Projection Formulas The specific identity of a monosaccharide is determined by the positioning of the other

OH groups

# Haworth Projection Formulas Any —OH group at a chiral center that is to the right in a Fischer projection formula points

down in the Haworth projection formula

# Haworth Projection Formulas OH group to the left in a Fischer projection formula points

up in the Haworth projection formula

# Haworth Projection Formulas . It is a pentose

Ribose

# Haworth Projection Formulas It is a ketose

Fructose

# Haworth Projection Formulas Its cyclic form has a 6-membered ring.

Glucose, galactose

# Haworth Projection Formulas Its cyclic form has two carbon atoms outside the ring.

Fructose

# Reactions of Monosaccharides Five important reactions of monosaccharides

– Oxidation to acidic sugars – Reduction to sugar alcohols – Glycoside formation – Phosphate ester formation – Amino sugar formation

# Reactions of Monosaccharides The redox chemistry of monosaccharides is closely linked to the alcohol and aldehyde functional groups present in them.

Oxidation to acidic sugars

# Reactions of Monosaccharides Weak oxidizing agents

**Tollens and Benedict’s solutions ** oxidize the aldehyde end to give an aldonic acid.

# Reactions of Monosaccharides can oxidize both ends of a monosaccharide at the same time (the carbonyl group and the terminal primary alcohol group) to produce a dicarboxylic acid

Strong oxidizing agents

# Reactions of Monosaccharides are known as aldaric acids

polyhydroxy dicarboxylic acids

# Reactions of Monosaccharides In biochemical systems enzymes can oxidize the primary alcohol end of an aldose such as glucose, without oxidation of the aldehyde group, to produce an

alduronic acid

# Reactions of Monosaccharides The carbonyl group in a monosaccharide (either an aldose or a ketose) is reduced to a hydroxyl group using hydrogen as the reducing agent

Reduction to sugar alcohols

# Reactions of Monosaccharides The product is the corresponding polyhydroxy alcohol

sugar alcohol

# Reactions of Monosaccharides used as moisturizing agents in foods and cosmetics and as a sweetening agent in chewing gum

Sorbitol

# Reactions of Monosaccharides Cyclic forms of monosaccharides are hemiacetals, they react with alcohols to form acetals

Glycoside formation

# Reactions of Monosaccharides are called glycoside

Monosaccharide acetals

# Reactions of Monosaccharides is an acetal formed from a cyclic monosaccharide by replacement of the hemiacetal carbon —OH group with an —OR group

glycoside

# Reactions of Monosaccharides A glycoside produced from glucose

glucoside

# Reactions of Monosaccharides Glycosides exist in both

Alpha and Beta forms

# Reactions of Monosaccharides Human blood is classified into four types: A, B, AB, and O

Blood Types and Monosaccharides

# Reactions of Monosaccharides Blood of one type cannot be given to a recipient with

blood of another type

# Reactions of Monosaccharides A transfusion of wrong blood type can cause the blood cells to form

clumps

# Reactions of Monosaccharides People with type O blood are

universal donors

# Reactions of Monosaccharides those with type AB blood are

universal recipients

# Reactions of Monosaccharides In the United States type O blood is the

most common

# Reactions of Monosaccharides type A the

second most common

# Reactions of Monosaccharides The monosaccharides responsible for blood groups

D-galactose and its derivatives

# Reactions of Monosaccharides The hydroxyl groups of a monosaccharide can react with inorganic oxyacids to form inorganic esters.

Phosphate ester formation

# Reactions of Monosaccharides are stable in aqueous solution and play important roles in the metabolism of carbohydrates

Phosphate esters

# Reactions of Monosaccharides one of the hydroxyl groups of a monosaccharide is replaced with an amino group

amino sugar

is replaced by an amino group

carbon 2 hydroxyl group

# Reactions of Monosaccharides are important building blocks of polysaccharides such as chitin

Amino sugars and their N-acetyl derivatives

Two monosaccharides can react to form

disaccharide

One monosaccharide act as a____ __________ and the other as ____________________ ___________

hemiacetal & alcohol

is produced as an intermediate in the hydrolysis of the polysaccharide cellulose

Cellobiose

Cellobiose contains

**two b - D-glucose monosaccharide units** linked through a **b (1—4) glycosidic linkage**

cannot be digested by humans.

cellobiose

is digested easily by humans because we have enzymes that can break a (1-4) linkages but not b (1-4) linkages of cellobiose

Maltose

is made up of b-D-galactose unit and a b-D- glucose unit joined by a b(1-4) glycosidic linkage

Lactose

principal carbohydrate in milk

Lactose

Human - _____________ __lactose

7%–8%

cow’s milk -

4%–5% lactose

a condition in which people lack the enzyme lactase needed to hydrolyze lactose to galactose and glucose

Lactose intolerance

b(1-4) glycosidic linkages

Lactase hydrolyzes

The most abundant of all disaccharides and found in plants

Sucrose (table sugar)

It is produced commercially from the juice of sugar cane and sugar beets

Sucrose (table sugar)

contains up to 20% by mass sucrose

Sugar cane

contain up to 17% by mass sucrose

Sugar beets

Disaccharides

Cellobiose Maltose Lactose Sucrose

Two different monosaccharide units are present

Lactose, sucrose

Hydrolysis produces only monosaccharides

Maltose, cellobiose, lactose, sucrose

Its glycosidic linkage is a “head-to-head” linkage

Sucrose

It is not a reducing sugar

Sucrose

Many monosaccharide units bonded with glycosidic linkages

Polymers

PolymersTwo types

Linear and branched homo- and hetero-polysaccharides

are not sweet and don’t show positive tests with Tollen’s and Benedict’s solutions whereas monosaccharides are sweet and show positive tests

Polysaccharides

Limited water solubility

Polysaccharides

# Polysaccharides starch in plants

Cellulose

# Polysaccharides in animals

Glycogen

# Polysaccharides in arthropods

Chitin

# Starch is a polysaccharide that is a storage form for monosaccharides and is used as an energy source in cellsstorage polysaccharide

storage polysaccharide

is the monomeric unit

Glucose

Two types of polysaccharidse isolated from starch

Amylose & Molecular Mass

Straight chain polymer - 15 - 20% of the starch and has a (1  4) glycosidic bonds

startch Amylose

50,000 (up to 1000 glucose units)

Starch Molecular Mass

Branched chain polymer - 80 - 85 % of the starch a (14) glycosidic bond for straight chain and a (16) for branch

Amylopectin Stucture

Molecular Mass: 300,000 (up to 100,000 glucose units) - higher than amylose

Amylopectin

Humans and animals storage polysaccharide

Glycogen

Contains only glucose units

Glycogen

Branched chain polymer – a (14) glycosidic bonds in straight chains and a (16) in branches

Glycogen

Molecular Mass: 3,000,000 (up to 1,000,000 glucose units)

Glycogen

Three times more highly branched than amylopectin in starch

Glycogen

Excess glucose in blood stored in the form of glycogen

Glycogen

Linear homopolysaccharide with b (1  4) glycosidic bond

Cellulose

Up to 5000 glucose units with molecular mass of 900,000 amu

Cellulose

Cotton cellulose and wood

~95% & ~50%

It serves as dietary fiber in food-- readily absorbs water and results in softer stools

Cellulose

dietary fiber is desired everyday

20 - 35 g

Similar to cellulose in both function and structure

Chitin

Linear polymer with all b (14) glycosidic linkages - it has a N- acetyl amino derivative of glucose

Chitin

Function is to give rigidity to the exoskeleton s of crabs, lobsters, shrimp, insects, and other arthropods

Chitin

polysaccharides with a repeating disaccharide unit containing an amino sugar and a sugar with a negative charge due to a sulfate or a carboxyl group.

Acidic polysaccharides

present in connective tissue associated with joints, cartilage, synovial fluids in animals and humans

Structural polysaccharide

is lubrication necessary for joint movement

Primary function of Acidic polysaccharides

have more than one type of monosaccharide monomers is present

heteropolysaccharides

heteropolysaccharides ex;

– Hyaluronic acid – Heparin

Alternating residues of N- acetyl-b-D-glucosamine and D-glucuronic acid

Hyaluronic acid

serve as lubricants in the fluid of joints and part vitreous humor of the eye.

Highly viscous

An anticoagulant-prevents blood clots

Heparin

Polysaccharide with 15–90 disaccharide residues per chain

Heparin

is a lipid molecule that has one or more carbohydrate (or carbohydrate derivative) units covalently bonded to it.

glycolipid

is a protein molecule that has one or more carbohydrate (or carbohydrate derivative) units covalently bonded to it

glycoprotein

Foods high in carbs content constitute over _______ of the diet of most people of the world

50%

- a balanced dietary food should contain about

60% of carbohydrate

Corn in

South America

Rice in

Asia

Starchy root vegetables in parts of

Africa

Potato and wheat in

North America

Nutritionist divide dietary carbs into two classes:

Simple carb & Complex carbs

dietary monosaccharides or disaccharides - sweet to taste commonly referred to as sugars - 20 % of the energy in the US die

Simple carb

Dietary polysaccharides -- starch and cellulose - normally not sweet to taste

Complex carbs

A developing concern about intake of carbohydrates involves how fast the given dietary carbs are broken down to glucose within the human body

Glycemic Foods

Glycemic effect refers to

– how quickly carbs are digested – how high blood glucose rise – how quickly blood glucose levels return to normal

has been developed for rating foods

Glycemic index (GI)

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