Final Flashcards
Monosaccharides
Combine two organic chemical functional groups:
1. Carbonyl (C=O) group, which is either an aldehyde or a
ketone, AND
2. at least two carbons bearing hydroxyl (alcohol) (-C-OH)
groups.
polyhydroxy-aldehydes (Aldoses)
or
polyhydroxy-ketones (Ketoses)
Chemical properties of monosaccharides
very water-soluble
* poorly soluble or insoluble in organic solvents such
as ether or hexane
* colourless
* most are sweet to the taste
* Approx. formula (CH2O)n
10
The simplest monosaccharides
contain three
carbon atoms (Trioses)
Fischer projection formulas to represent three-dimensional
sugar structures on paper
Emil Fischer
Enantiomers
Mirror Images - Differ in configuration at every chiral
carbon atom.
* Commonly called “left-handed” and “right-handed”
forms of a molecule.
* Have identical chemical properties (e.g. melting
point, water-solubility)
* Differ in “optical activity” - the plane of polarization
of polarized light is bent in opposite directions when
passing through solutions of the two enantiomers.
Diastereomers
- Monosaccharides with more than one
chiral carbon atoms have stereoisomers
that differ in handedness at some
carbon atoms but not at others. - do not have identical
chemical properties
Epimers
A pair of sugars that are identical except for the
configuration at one carbon atom
Hemiacetal and hemiketal formation turns sugars into
ring structures.
found either in the α or the β form of the hemiacetal
Solid glucose
mutarotation
solid glucose When dissolved in water, it slowly converts into an equilibrium
mixture of the alpha, beta, and linear forms
ring form: pyranose
6 membered
ring forms: furanose
5 membered
The anomeric carbon atom of a sugar (the only carbon attached to two
oxygen atoms) is
electrophilic
In principle, any -OH group on a sugar can act as a nucleophile
and form a glycosidic bond to the anomeric carbon atom of another sugar. This is
how sugars are assembled into polymers (oligosaccharides) such as starch and cellulose
If the anomeric carbon is involved in a glycosidic bond the sugar becomes a
non-reducing sugar
A disaccharide is formed when
when two monosaccharides are
linked through a glycosidic bond.
The reaction of a disaccaride forming occurs when
the anomeric carbon (electrophile)
of one sugar reacts with a hydroxyl group (nucleophile)of the
other
Lactose is a disaccharide formed by the
condensation of
glucose with galactose
the glycosidic bond is described a
(β1→4): going from
C-1of galactose in the β configuration to C-4 of glucose
Lactose is named
gal(β1→4)glc
sucrose is a ____ sugar
non- reducing
Homopolysaccharides
made from a single type of
sugar monomer
Heteropolysaccharides
made from two or more kinds of
sugar subunits
Why is glucose stored as glycogen
(animals) and starch (plants) and
not in its free form?
to not upset the osmotic balances in the cell. Glucose molecules are soluble in water and thus can cause the cell to become hypertonic. This will result in the entry of water molecules within the cells and cause it to lyse.
Friedrich Miescher
first isolated DNA
Nucleic acids are ____ polymers
made by connecting nucleotides via
______ bonds
linear, phosphodiester
The OH group undergoes _____ tautomerism
keto/ enol
The NH2 group undergoes ________ tautomerism.
amino/ imino
The phosphate groups are completely
ionized and ______ charged at pH 7
negatively
phosphate groupe 5’ end has a __ charge
-2
if theres oh groups at 3’ and 5’ end
no charge
The 2′ hydroxyl of RNA, which is absent from DNA, acts as a
_______ in an intramolecular displacement, breaking the
_______ linkage.
nucleophile, phosphodiester
Why are triacylglycerols such a good source of fuel storage
Because they are insoluble in water large amounts can be stored in cells
without increasing the osmotic pressure of the cytosol. The hydrophobicity also
allows the storage of TAGs without the added weight of hydration
Why are triacylglycerols not a significant component of biological membranes?
TAGs are completely hydrophobic.
Therefore, they cannot assemble into a bilayer structure to form membranes.
If ninhydrin is used to detect phospholipids separated using thin
layer chromatography, which of the phospholipids discussed in class would you be
able to detect?
Phosphatidylethanolamine and phosphatidylserine as they both contain primary
amino groups.
Differentiate between a nucleoside and a nucleotide.
A nucleoside is a base attached to a ribose (or deoxyribose) sugar. A nucleotide is a
nucleoside with one or more phosphoryl groups attached to the sugar.
The cyclization of glucose
Generates a new chiral carbon atom
The complete hydrolysis of one mole of phosphatidylglycerol yields the components fatty acid, glycerol and phosphate, in which of the following respective molar ratios?
2:2:1
Chargaff’s rules
A = T , G = C
who Used X-ray crystallography to identify
the secondary structure of DNA
Rosalind Franklin and Maurice Wilkins
who obtained
the first useful X-ray
diffraction images of DNA:
“photo 51”
Rosalind Franklin