CARBOHYDRATE

Agustina Setiawati, M.Sc.,

Apt
Yunita Linawati, M.Sc., Apt

Adapted from: bio.classes.ucsc.edu/bio100/BIO100Summer

Reference: Lehninger: Principles of Biochemistry, 5 th edition

Don'tmemorizestructures,but
knowtheimportantfeatures

Carbohydrates
They are important for energy storage, cell-cell signaling and cell wall structures.
Most have the formula (CH2O)n
Three major classes of carbohydrates: mono, oligo, poly saccharides
Monosaccharides are single sugars and can be divided into 2 groups: aldoses, which have
aldehyde groups, and ketoses, which have ketone groups.

R1
C
R2

Aldehydeisacarbonyl(C=O)whereOneRgrpisH
KetoneisacarbonylwhereNoRgrpisH

TERMINOLOGY

Aldoses

Ketoses

D and L

Solid wedge-shaped bonds point toward the reader, dashed wedges point away.

Epimers

D-Glucose

and two of its epimers are shown as projection formulas. Each epimer differs from
D-glucose in the configuration at one chiral center (shaded pink).

Formation of hemiacetals and hemiketal

An aldehyde or ketone can react with an alcohol in a 1:1 ratio to yield a hemiacetal or hemiketal, respectively, creating a
new chiral center at the carbonyl carbon. Substitution of a second alcohol molecule produces an acetal or ketal. When
the second alcohol is part of another sugar molecule, the bond produced is a glycosidic bond.

Rings
In aqueous solution, monosaccharides
with
five or more C atoms in the backbone
occur
as cyclic (ring) structures in which the
carbonyl group has formed a covalent
bond with the O of a hydroxyl group
along the chain.
These 6-membered ring compounds
are
called pyranoses.
These rings form due to a general
reaction that occurs between alcohols
and aldehydes or ketones to form
derivatives called
hemiacetals or hemiketals.
Anomers are isomeric forms of
monosaccharides that differ only in
their
configuration about the hemiacetal
or hemiketal C.

 Glucose (an aldose) can

cyclize to form a cyclic
hemiacetal
Fructose (a ketose) can
cyclize to form a cyclic
hemiketal
Cyclic form of glucose is
a pyranose
Cyclic form of fructose is
a furanose

Sugarsarereducingagents

Oxidation of the anomeric carbon of glucose under alkaline conditions.

The reaction with Cu2+ is complex, yielding a mixture of products

Glycosidic bond
Disaccharide is formed from two
monosaccharides (here, two
molecules of D-glucose) when an
OH (alcohol) of one glucose molecule
(right) condenses with the
intramolecular hemiacetal of the other
glucose molecule (left), with
elimination of H2O and formation of a
glycosidic bond. The reversal of this
reaction is hydrolysisattack by H2O
on the glycosidic bond. The maltose
molecule, shown here as an
illustration, retains a reducing
hemiacetal at the C-1 not involved in
the glycosidic bond. Because
mutarotation interconverts the a and
b forms of the hemiacetal, the bonds
at this position are sometimes
depicted with wavy lines, as shown
here, to indicate that the structure
may be either a or b.

Common
Disaccharides

Polysaccharides

Polysaccharidescanhaveone,
twoormanydifferent
monosaccharides

POLYSACCHARIDE: Starch
A plant storage
polysaccharide
Two forms: amylose and amylopectin
Most starch is 10-30% amylose and 70-90%
amylopectin
Branches in amylopectin every 12-30 residues
Amylose has alpha(1,4) links, one reducing
end

Amylose and amilopektin

A short segment of amylose, a linear polymer of D-glucose residues in (14) linkage.

Amylopectin has stretches of similarly linked residues between branch points.

Amilopectin

POLYSACCHARIDE: GLYCOGEN
A plant storage polysaccharide
Glycogen is stored energy for the organism
Only difference from starch: number of
branches
Alpha(1,6) branches every 8-12 residues
(more branches than amylopectin)
Like amylopectin, glycogen gives a red-violet
color with iodine

Polysaccheride: Cellulose

Humanenzymescandigesta14butnotb14glycosidiclinkages
Cellulaseinmicrobescanbreakdownb14linkages
(Ruminantshavemicrobesinstomach)

POLYSACCHARIDE: DEXTRAN
Asmallbutsignificantdifferencefromstarchand
glycogen
If you change the main linkages between
glucose from alpha(1,4) to alpha(1,6), you
get a new family of polysaccharides dextrans
Branches can be (1,2), (1,3), or (1,4)

POLYSACCHARIDE:
Chitin

A short segment of chitin, a homopolymer of Nacetyl-D-glucosamine units in (14) linkage.

Chitin is hard exoskeleton

POLYSACCHARIDE:
AGAROSE

OTHER POLYSACCHARIDE:
GLYCOSAMINOGLICAN

Glycoproteins

THANK YOU