Carbohydrates

In biochemical perspective, a carbohydrate is defined as polyhydroxy

aldehyde or ketone.

The presence of the aldehyde and ketone groups divide

carbohydrates into two major groups namely aldoses and
ketoses

Aldehyde: H-C=O
Ketone: O=C-CH2OH

The number of carbons may also be indicated by adding syllables in

the carbohydrates name:
ALDOHEXOSE- Aldo(aldehyde) HEX (Six) Ose (Carb group)

Glyceraldehyde aldotriose
Dihydroxyacetone ketotriose
Same molecular formula but different functional groups =
Tautomers

Like most organic compounds, carbohydrates have CHIRAL or

ASSYMETRIC carbons
For carbohydrates with more than one chiral
center, the D or L designation is determined
by the hydroxyl group farthest from the
carbonyl carbon.

In nature, the most abundant

carbohydrates exist as D
enantiomeric forms while L isomers
are rare.

Sugars only differ in only one chiral

carbon such as the case of D-
mannose and D-glucose at C2.
These are called epimers.

Cyclization (Making into

haworth or chair conformation) results to formation of a NEW chiral
center in carbon 1, hence leading to formation of ANOMERS designated
as alpha (OH below the ring) or beta (OH above the ring)
conformation which may interconvert through mutarotation

TYPES OF CYCLIC CARBOHYDRATES

Sugars in ring conformation may adopt a six-membered or a
five-membered closed structures which resembles pyran
and furan rings.

CLASSIFICATION OF CARBOHYDRATES
Carbohydrates are classified according to the number of sugar units
(Monomers) they contain:
a.Monosaccharides

b.Disaccharides Carbohydrates composed of two sugar units joined by

a glycosidic bond

c.Oligosaccharides

d.Polysaccharides

Glycosidic bond-

Can be 1 2 bond or 1 3 bond or 1 4 bond.

Oligosaccharides are made up of 3-10 monomeric sugar units which

are commonly attached to proteins or lipids such as the ABO antigens.
Polysaccharides Carbohydrates composed of long chains of sugar
molecules, usually more than ten residues.
Polysaccharides play significant roles in organisms as they serve as
energy storage (glycogen and starch), provide structure (cellulose and
chitin) as well as protection to host (bacterial cell wall of Gram positive
bacteria).
Functions of Carbohydrates:
1.Energy Source
2.Structural Support
3.Cell-mediated recognition

Amylose and Amylopectin of Storage Carbohydrates

The principal storage polysaccharides are amylose and
amylopectin. These polymers are made up of a-D-
glucopyranose which differ in glycosidic linkage.

Storage Carbohydrates: Glycogen and Starch

Starch, the primary carbohydrate storage molecule in plants and

Glycogen in animal liver and skeletal muscles both contain
amylose and amylopectin but differ in the frequency of branching
points.

Starch has branch points every 24-30 residues.

Glycogen has branch points every 8-12 residues

Structural Polysaccharides: Chitin and Cellulose

Chitin
Chitin is a polymer made up of N-acetyl-B-D-glucosamine. It is
generally found in invertebrates as a major composition of
exoskeletons of arthropods and mollusks.

Cellulose on the other hand is made up of long chains of B-D-glucose

which are held intact by hydrogen bonds giving plant cell walls stability
and high tensile strength.

Glycosaminoglycans
Unbranched polysaccharides that consists of alternating uronic acid
and hexosamine residue

Hyaluronic acid component of connective tissue, synovial fluid, and

vitreous humor. Serves as shock absorbers and lubricants

Heparin not a constituent of connective tissue; occurs in the

intracellular granules of mast cells in arterial walls.

Heparan sulfate ubiquitous cell surface component; extracellular

substance in blood vessels and brain
Plants dont produce glycosaminoglycans

Glycoproteins
The polypeptide chains of glycoprotein are synthesized under genetic
control
Carbohydrate chains are enzymatically added and covalently linked
to the polypeptide chain without the guidance of the nucleic acid
template --- microheterogeneity
Types:
Proteoglycan
Peptidoglycan
Glycosylated protein
Proteoglycan
The brushlike structure of proteoglycans, together with the
polyanionic character of keratan sulfate and chondroitin sulfate
cause these complexes to be highly hydrated.

As a result, these complexes have high resilience

Peptidoglycans
Gram positive bacteria have peptidoglycan layers in their surface
which contains carbohydrates. Since carbohydrates have polyhydroxyl
groups that form hydrdogen bond with water, Gram positive bacteria
can be stained by dyes dissolved in water