carbohydrates (b1- foundation) Flashcards

(65 cards)

1
Q

carbohydrate definition

A

polyhydroxyl alcohols with aldehyde or ketone groups

needs to have at least 3 n’s in (CH2O)n otherwise not classified a carbohydrate

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2
Q

what are the functions/biochemical significance of carbohydrates?

A
  1. Main source of energy/energy production- brain cells & RBC’s almost wholly depend on carbs as energy source
  2. Glycoproteins and glycolipids are components of cell membranes & receptors
  3. Storage form of energy (starch and glycogen are the storage forms)
  4. excess carbohydrate is converted to fat
  5. structural basis of many organisms: cellulose of plants, exoskeleton of insects, cell wall of microorganisms, mucopolysaccharides as ground substances in higher organisms

basically just all has to do with energy

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3
Q

what does classification of carbohydrates depend on?

A

on hydrolysis

on how hydrolyzed they can be
- ex. monosaccharides cannot be hydrolyzed further

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4
Q

what are the 4 classifications of carbohydrates? (do not confuse w/ classifications of monosaccharides!!) w/ examples of each

A

1. Monosaccharides: 1 unit-simple sugar
- *ex: glucose, fructose, galactose

2. Disaccharides: 2 monosaccharides
- ex: sucrose, lactose, maltose

3. Oligosaccharides: 2-10 monosaccharides
- ex: raffinose & stachyose

4. Polysaccharides: 10+ monosaccharides
- further divided into heteropoly & homopoly saccharides
- ex: glycogen, GAGs, starch, cellulose

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5
Q

what are the 2 further classifications of polysaccharides and what are their examples?

A

homopoly saccharides: long chains made up of only 1 type of sugar
- ex: glycogen, starch, cellulose

heteropoly saccharides: long chains made up of different types of sugars
- ex: GAGs, glycoproteins, proteoglycans

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6
Q

what are the 2 basis that monosaccharides are further classified on?

A
  1. According to functional group (aldoses & ketoses)
  2. According to the # of carbon atoms
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7
Q

monosaccharide classification based on functional group + examples

A

aldoses: have aldehyde group (-CHO)
- ex. glucose

ketoses: have ketone group (C=O)
- ex. fructose

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8
Q

monosaccharide classification according to number of carbon atoms

A

Trioses: 3 carbon atoms
- ex: glyceraldehyde, dihydroxyacetone

Tetroses: 4 carbon atoms
- ex. erythrose, erythrulose

Pentoses: 5 carbon atoms
- ex. ribose, ribulose

Hexoses: 6 carbon atoms
- ex. glucose, fructose

first example is the aldose sugar, second is the ketone sugar

we stop at hexose even though there are further classifications after that

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9
Q

glyceraldehyde, structure, and the 2 types

A

smallest simple sugar - reference sugar
- has 3 carbon atoms but only 1 is chiral

position of OH group on chiral (asymmetric) carbon
- if on the rightD type
- if on the leftL type

D-glyceraldehyde:
H - C = O
|
H - C - OH
|
CH2OH

L-glyceraldehyde:
H - C = O
|
OH- C - H
|
CH2OH

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10
Q

biochemical significance of D-Ribose

A

pentose (monosaccharide)

found in nucleic acid

importance: structural element of nucleic acid & coenzymes
- ex. ATP, NAD, NADP, Flavoproteins, Ribulose phosphate

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11
Q

dietary classification of carbohydrates (I dont think this is too high yield tho)

A

carbohydrates → simple & complex

simplesugars → mono & disaccharides

complexstarches & fiber

fiber → soluble & insoluble

this I just wrote out roughly

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12
Q

definition of stereoisomerism

A

compounds with the same structural formula but different spatial orientation of groups called stereoisomers (like glucose, fructose, mannose, & galactose)

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13
Q

what are 2 types of carbon atoms? (chiral & penultimate)

A

chiral/asymmetric: 4 different atoms or groups are attached

penultimate: 2nd last carbon (next to last)

counting of carbon atoms changes based on functional group/double bond (remember the whole numbering system

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14
Q

most naturally occurring sugars are what type of isomer?

A

D isomer

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15
Q

sugars that have more than 1 chiral carbon are classified as D & L types based on what?

A

position of the OH group on penultimate (second to last) asymmetric carbon atom

  • whether on the right or left
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16
Q

epimers vs isomers

A

epimers: differ in configuration around ONLY ONE carbon atom
- ex. glucose & mannose are C2 epimers

isomers: differ in configuration around 2+ carbon atoms
- ex. galactose & mannose are isomers

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17
Q

“D & L” isomerism / enantiomers

A

in structures that are mirror images of each other (enantiomers)

  • OH group farther from the C=O has to be on the right to be D-isomer
  • OH group farthest from the C=O has to be on the left to be L-isomer
    basically penultimate carbon

think L for left

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18
Q

example of epimerism (mannose & galactose)

A

mannose → C2 epimer of glucose (H is on the right instead, OH is on the left instead at 2nd carbon)

galactose → C4 epimer of glucose (H is on the right instead of OH, OH on left instead at 4th carbon)

think that mannose has 2 n’s so its the C2 epimer, the other one is the C4 epimer

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19
Q

fischer projection of glucose

A

H – C = O
|
H – C – OH
|
HO – C – H
|
H – C – OH
|
H – C – OH
|
CH2OH

1st & 5th are achiral b/c double bond & multiple H’s attached

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20
Q

what is an anomeric carbon? UQ

A

in water, glucose folds into a ring (OH group on carbon 5 reacts w/ carbonyl group) so use haworth projection (the ring ones)

anomeric carbon: carbon that was part of the carbonyl group (the aldehyde or ketone) before the ring formed
- after ring formation, becomes a new chiral center (this is v. imp!)

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21
Q

difference in ketoses & aldoses and how that affects the anomeric carbon + examples

A

in aldoses (like glucose) → carbonyl group (double bond to the C) is on C-1 so C-1 becomes the new anomeric carbon → becomes 6 membered ring
- ex: pyranose

in ketoses (like fructose) → carbonyl group is on C-2 so C-2 becomes the new anomeric carbon → becomes 5 membered ring
- ex: furanose

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22
Q

what are anomers and what are the 2 types?

A

anomers: isomers that differ in configuration around the anomeric carbon atom

α-anomers: OH is facing down in the haworth structure
- think a for away so the group is going away

β-anomers: OH is facing up in the haworth structure
- b for birds and birds fly so going up

example of α-D-glucose and β-D-glucose

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23
Q

what is optical isomerism?

A

chiral carbon (isomers only exist in chiral compounds) has the ability to rotate plane polarized light to the left or right

L (Levorotatory) or (-): means rotates to the left

D (dextrorotatory) or (+): means rotates to the right

NOT THE SAME AS D & L ISOMERISM WHICH ARE ENANTIOMERS & BASED ON HOW IT LOOKS NOT HOW IT ROTATES LIGHT

sugars can be designated either D (-), D (+), L (-), or L (+)

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24
Q

list the 4 types of isomerisms we discussed

A
  1. D & L isomerism (enantiomers)
  2. Epimers
  3. Anomers
  4. Optical Isomerism
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25
how many chiral centers are in glucose & what is the significance?
**4 chiral centers** **significance**: gives isomers - D- glucose is beneficial for the body whereas L-glucose is used in artificial sweeteners (*good for diabetes b/c will enter blood and not get metabolized*) notes says to know this significance of D & L isomers
26
what is mutarotation? **UQ**
change in optical rotation that happens when a sugar is dissolved in water - **switches between its α and β forms** the 2 forms **interconvert** and as they interconvert, the way they rotate light also changes - pure α-D-glucose has rotation of **+112.2º** - pure β-D-glucose has rotation of **+18.7** overtime, the mixture at equilibrium equals **+52.7°**
27
bonds b/w monosaccharides/sugars are formed through what?
through **glycosidic linkage** by a condensation reaction
28
O-glycosidic linkages + 2 types
**O-glycosidic linkage**: formed b/w anomeric carbon of 1 sugar and the OH group of another sugar or molecule *2 types* **α-linkage**: OH from anomeric carbon was down (two alphas meet) **β-linkage**: OH from anomeric carbon was up (1 beta and 1 alpha meet)
29
why is sucrose called an invert sugar? (**imp**)
because when you break (hydrolyze) sucrose into glucose and fructose, the **direction of light rotation changes**, or inverts sucrose is (-) but when break it down, fructose overpowers so it becomes (+) *only sugar that does this* **enzyme used for hydrolysis**: sucrase or invertase
30
sucrose linkage
Glucose – fructose α 1→ 2 β *1st carbon of glucose, 2nd carbon of fructose* + free reducing groups not available disaccharide since made of 2 monosaccharides
31
what is a reducing sugar?
has a **free anomeric carbon** (anomeric carbon is not linked to anything else through glycosidic linkage) b/c whatever anomeric OH is free is whats going to make a bond *all monosaccharides are reducing sugars but all disaccharides are not*
32
lactose linkage
galactose + glucose β-1 – α-4 *1st carbon of galactose w/ 4th carbon of glucose* *lactose is diff from lactate/lactic acid- thats whats produced as a result of anaerobic respiration*
33
maltose linkage
glucose + glucose α1→ α4 (straight chain)
34
isomaltose linkage
glucose + glucose - alpha -1, alpha 6 linkage (branched chain b/c muscles dont have that much space for straight chain so branched to compact them together)
35
classifications of **homopolysaccharides** + examples
homopolysaccharides: same monosaccharide units **storage homopolysaccharides**: starch, glycogen, inulin, dextrin, dextran **structural homopolysaccharides**: cellulose, chitin
36
homopolysaccharides: **starch** (biochemical significane, linkage, and components)
**biochemical significance**: plants storage energy form, non-reducing sugar (*b/c too compacted that it's not rlly free anymore- non reducing bc of compaction not structure*) **linkage**: α1→ α4 & α1→ α6 **components**: 2 subunits - amylose & amylopectin
37
2 components of starch: amylose & amylopectin (components, importance, enzymes)
**1. amylose (15-20% of starch)**: long unbranched chain of thousands of D-glucose units - forms helices (coils) that trap iodine molecules (*which is why iodine test shows presence of starch*) - digested by *amylases* that hydrolyze alpha-1,4-glycosidic bonds **2. amylopectin (80-85% of starch)**: also made of D-glucose but **highly branched** - branches created by α-1,6 glycosidic bonds every 24-30 glucose units - most of the starch in **plants** is in this form - digested by **debranching enzymes** that hydrolyze α-1,6
38
action of amylases on starch
**salivary amylase** (mouth) and **pancreatic amylase** (intestine) break **α-1,4 bonds** randomly - produces smaller chains called **dextrins** that are eventually broken into **maltose** and **glucose**
39
glycogen (structure, importance, storage)
storage form of glucose in animals - large, branched molecule made entirely of **D-glucose** units **structure**: very similar to amylopectin but with more branches and more compact (has **α-1,4** & **α-1,6 linkages** - at the center of each glycogen molecule is a protein called **glycogenin** (is like a primer- starting point where glucose molecules begin to attach) **importance**: highly branched so more compact (can store more glucose in a small space) **storage**: 5% weight stored in liver, 1-2% stored in muscle
40
muscle vs liver storage of glycogen
**liver**: maintains blood glucose levels **muscle**: used for muscle energy only, muscles dont have enzyme **G6P** so they **cant convert stored glucose into free glucose** to release into the blood - *muscles are very selfish, they dont like to donate, keep everything for themselves*
41
only diff b/w glucose & glycogen
branching in glycogen
42
cellulose + structure
made of many D-glucose units (polysaccharide), found in plants esp cell walls, most abundant organic compound on earth **structure**: joined by **β-1,4 glycosidic bonds** = long, straight, unbranched chains = its really strong!!
43
why can't humans digest cellulose? so then what's it role in humans (3 roles)?
humans lack enzyme **cellulase** (or cellobiase) so cant break β-1,4 bonds in cellulose but it acts as **roughage (fiber)** for us **health benefits of roughage**: 1. increases bowel motility 2. prevents constiptation & hemorrhoids 3. lowers blood cholestrol (by interfering with its absorption) 4. industrial uses (paper, cotton, linen)
44
inulin (linkage + significance)
**linkage**: β-1,2 glycosidic linkages - made entirely of D-fructose units **significance**: renal function tests (used to test filtration rate & renal clearance value), injected and what you put in is what should come out (if not = problem w/ kidney) body can't digest but can absorb
45
chitin
made of special sugar called **N-acetyl-D-glucosamine** these sugar units joined by **β-1,4 glycosidic bonds** in **exoskeletons** of insects, crabs, shrimp, and other arthropods
46
dextrin + uses
intermediate in starch hydrolysis (starch breaks into this first) *has the same linkages as starch* **uses**: used in **wheat glue** and can be added to foods to help them stick together, used in pharmaceutical preparations to bind constituents of the pill, food preservative
47
dextrans (linkages, uses,
**large** (high molecular weight), **highly branched** polysaccharides synthesized by **microorganisms** **linkages**: Mainly α-1→6, with some α-1→3 and α-1→4 **uses**: mostly for medical uses, blood volume expanders, maintain blood plasma volume, helps prevent blood clots, organ transplantation storage
48
dextrose, dextrin, & dextran (*to not confuse these terms!*)
**dextrose**: another name for glucose, used in medical drips **dextrin**: partially digested product of starch **dextran**: synthesized by microorganism, highly branched glucose polymer, used medically & in Pharma
49
structure of GAGs
**GAGs** = glycosaminoglycans long, unbranched, heteropolysaccharide chains that are composed of repeating disaccharide units (1 acidic sugar- 1 amino sugar) - *synthesized in body from simple sugars*
50
8 functions of GAGs in the body
1. key components of **ECM** 2. Contribute to the **turgor** of various tissues: help w/ water retention too 3. Act as **sieves** in ECM: allow smaller molecules to pass through, prohibiting larger ones 4. Facilitate **cell migration**, act as **shock absorber** at joints 5. Maintenance of **compressibility of cartilage**: allow cartilage to compress & rebound, helping it absorb shock 6. Have a structural role in **sclera & in corneal transparency**: white part of eye 7. Act as anticoagulant 8. Formation of cell membrane and **synaptic vesicles**
50
classification of GAGs
sulphate free & sulphate containing **sulphate free** → hyaluronic acid (*only 1*) **sulphate containing** → - chondrotin sulphate - dermatan sulphate - keratan sulphate - heparin - heparan sulphate *all have sulphate in the name except for 1*
51
GAGs: hyaluronic acid (HA) - structure + where its found
linkages b/w disaccharides is **beta 1-4** but b/w the units themselves is **beta 1-3** **found in**: synovial fluid of joints, umbilical cord, loose connective tissue, & cartilage
52
functions of HA
1. Key component of synovial fluid which **lubricates joints** → helps maintain flexibility & strength by retaining water and keeping cartilage strong 2. stimulates production of synovial fluid 3. injectable **treatment for rheumatoid & osteoarthritis** 4. helps **deliver nutrients & removal of waste** from cartilage cells (they don't have blood supply) 5. Deficiency causes brittle and deteriorating joints 6. Helps in **wound healing** by promoting cell migration and increasing moisture at site of injury 7. **Cosmetic products** - injectable fillers that lessen appearance of lines, sagging, and depression of skin
53
how is heparin different from the other GAGs?
present intracellularly (inside the cell)
54
GAGs: **Heparin** (linkage, function, where its found)
**Linkage**: alpha 1→ 4, disaccharide units of glucoronic or iduronic acid & glucosamine **location**: found in mast cells lining arterial vasculature of liver, skin, spleen, lungs, and monocytes (*not an LO tho*) **function**: serves as anticoagulant
55
GAGs: **heparan sulfate** (
**function**: regulates biological activities including angiogenesis (new blood vessel formation), blood coagulation, and tumor metastasis **linkage**: same as heparin (alpha 1-4) **location**: basement membranes, component of cell surfaces
55
heparin vs heparan sulfate
**heparan sulfate** has a greater proportion of GliA (glucuronic acid), is less sulfated than heparins, and is present extracellularly
56
GAGs: chondroitin sulfate (linkage, location, functions)
*"chondra" stands for cartilage* **location**: ground substance of connective tissues, widely distributed in cartilage, bones, tendons, cornea, and skin **linkage**: beta 1,3 and beta-1,4 **structure**: galactosamine sulphate & glucuronic acid (GlcA) **functions**: provides strength & elasticity, maintains water retention, important for joint health, structural support
57
GAGs: **dermatan sulfate**
**structure/linkage**: repeating units of iduronic acid & N-acetylgalactosamine - linked by **β-1,3** bonds **location**: largely in skin (*derma for skin*), blood vessels, heart valves **functions**: structural support, resists mechanical stress, role in wound healing
58
keratan sulfate
linkages: **β-1,3** & **β-1,4** **components**: galactose & N-acetylglucosamine different from other GAGs bc **no uronic acid** **location**: tendons, loose connective tissues, cornea
59
glycoproteins + glycosylation
**glycoproteins**: proteins that have *oligosaccharides* (sugar chains) covalently attached to them sugars attached through 2 types of glycolysation: 1. **co-translational glycosylation**: happens while protein is still being made (during translation on the ribosome) 2. **post-transational glycosylation**: happens AFTER protein is fully made, during further processing inside ER or Golgi
60
different **glycoproteins** have different amounts of sugar depending on what?
what they do in the body *examples on slides*: **immunoglobin (IgG)**: only 4% of it is carb b/c its main job is fighting infections so needs more protein structure **mucin**: unto 80% carbs! sugars make it slippery, sticky, and protective -- perfect for lining & protecting surfaces
61
classes of glycoproteins
can be divided into 2 major classes based on **nature of linkage** b/w protein (polypeptide) & sugar (oligosaccharides) chains **O-linked**: sugar (glycan) attached to O atom of amino acids **serine or threonine** **N-linked**: sugar (glycan) attached to N atom of **asparagine**
62
biochemical significance of **glycoproteins** (6 roles)
1. Almost all proteins found in **plasma** (*liquid part of blood*) are glycoproteins except **albunim** 2. Components of ECM: hold tissues together - glycoproteins in **collagen** help with tissue strength & flexibility 3. **Protective biological lubricants**: muffins in the gastrointestinal and urogenital tracts 4. **Immune response**: antibodies (IgG, IgA) are glycoproteins 5. **Cell-surface recognition**: help cells recognize and interact w/ other cells, hormones, viruses 6. mane **Enzymes** are glycoproteins: oxidoreductases, transferases, hydrolases
63
proteoglycans + structure
huge molecules made **mostly of carbohydrate** (GAGs) and a **little protein**. - help build & support tissues in body—especially in cartilage, skin, and the extracellular matrix (ECM) **structure**: made of a core protein + long chains of GAGs attached to it - are **negatively charged** b/c of sulfate & carboxyl groups in GAGs - look like a bottle brush under microscope