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Carbohydrates
Carbohydrates
 Most

abundant class of biological molecules on

Earth
 Originally

produced through CO2 fixation during

photosynthesis
Roles of Carbohydrates
 Energy

storage (glycogen,starch)

 Structural
 Cellular

components (cellulose,chitin)

recognition

 Carbohydrate

derivatives include DNA, RNA, co-

factors, glycoproteins, glycolipids
Carbohydrates
 Monosaccharides

(simple sugars) cannot be broken

down into simpler sugars under mild conditions
 Oligosaccharides
 Polysaccharides

= "a few" - usually 2 to 10

are polymers of the simple sugars
Monosaccharides
 Polyhydroxy

ketones (ketoses) and aldehydes

(aldoses)
 Aldoses

and ketoses contain aldehyde and ketone

functions, respectively
 Ketose

named for “equivalent aldose” + “ul”

inserted
 Triose,

tetrose, etc. denotes number of carbons

 Empirical

formula = (CH2O)n
Monosaccharides are chiral
 Aldoses

with 3C or more and ketoses with 4C or more

are chiral
 The

number of chiral carbons present in a ketose is

always one less than the number found in the same
length aldose
 Number

of possible steroisomers = 2n (n = the number

of chiral carbons)
Stereochemistry
 Enantiomers
 Pairs

= mirror images

of isomers that have opposite configurations at

one or more chiral centers but are NOT mirror images
are diastereomers
 Epimers

= Two sugars that differ in configuration at

only one chiral center
Cyclization of aldose and ketoses
introduces additional chiral center
 Aldose

sugars (glucose) can cyclize to form a
cyclic hemiacetal
•Ketose sugars (fructose) can cyclize to form a
cyclic hemiketal
Haworth Projections
O

H

-OH up = beta
-OH down = alpha

C1
H

C2

OH

HO

C3

H

H

C4

OH

H

C5

OH

CH2OH

6
5
4

1
3

2

Anomeric carbon
(most oxidized)

For all non-anomeric carbons, -OH groups point down in
Haworth projections if pointing right in Fischer projections
Monosaccharides can cyclize to form
Pyranose / Furanose forms
a = 64%
b = 36%

a = 21.5%
b = 58.5%

a = 13.5%
b = 6.5%
Conformation of Monosaccharides

Pyranose sugars not planar molecules, prefer to be in
either of the two chair conformations.
Reducing Sugars
 When

in the uncyclized form, monosaccharides act

as reducing agents.
 Free

carbonyl group from aldoses or ketoses can

reduce Cu2+ and Ag+ ions to insoluble products
Derivatives
of
Monosaccharides
Sugar Phosphates
Deoxy Acids
Amino Sugars
Sugar alcohols
Monosaccharide structures you
need to know


Glucose



Fructose



Ribulose



Glyceraldehyde



Dihydroxyacetone

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Introduction carbohydrates