CARBOHYDRATE

CHEMISTRY
LOURDES L. BALCUEVA, M.D.

CARBOHYDRATE CHEMISTRY
Most abundant biomolecule in nature
Widely distributed in plants and animals
Main source of energy in humans;
oxidation of carbohydrates is the central
energy-yielding pathway in most nonphoto-synthetic cells

Carbohydrate Chemistry
Other functions of CHO:
- insoluble carbohydrate polymers serve
as protective and structural elements in
bacterial cell walls , plants, and
connective tissues of animals
- lubricate skeletal joints
- attached to proteins, act as signals that
determine intracellular location of glucoprotein

CARBOHYDRATE CHEMISTRY
- Carbohydrates are aldehyde or ketone
derivative of polyhydric alcohol
- General formula: Cn(H2O)n
- Ex. Glucose: C6H12O6
- Glucose- most important carbohydrate;
most dietary CHOs are absorbed in the
circulation as glucose;
- Glucose is the major metabolic fuel of
mammals and fetuses.

NOMENCLATURE
1. Monosaccharides- carbohydrate
molecules with only one actual or
potential sugar group;
- cannot by hydrolyzed into simpler
carbohydrates
2.Disaccharides- when 2 monosaccharides
are combined together with release of
water molecule; hydrolysis produces 2
monosaccharide units

Carbohydrates
3. Oligosaccharides- condensation
products of 2-10 monosaccharide units
4. Polysaccharides- condensation
products of more than 10
monosaccharides

Monosaccharides
- colorless, crystalline solids
- soluble in water but not in non-polar
solvents
- sweet taste
- backbone is unbranched C chain; all
carbon atoms are linked by single bonds
- One C atom is double-bonded to an
oxygen atom to form carbonyl grp.

Aldose and ketose

Aldose- if the carbonyl grp. is at the end of
the carbon chain; monosaccharide
is an aldehyde
Ketose- if the carbonyl grp. is at any other
position; monosacharide is a
ketone

Monosaccharides

Structure of Glucose

Haworth and Chair Form

Monosacchides
- monosaccharides with 5 or more carbon
atoms in the backbone occur as cyclic
structures in solution
- carbonyl grp. forms covalent bond with
oxygen of a hydroxyl grp along the chain

Stereoisomers
Stereoisomers-compounds having the
same structural formula but differ in spatial
configuration
- depends on the number of asymmetric C
atom
- formula: 2n where n is the number of
asymmetric carbon atom
- ex. Glucose: 2n is equal to 16

Diastereo-isomers
Monosaccharides with the same molecular
Formula but differ in the configuration about 2
carbon atoms
Ex. Mannose and galactose
Epimers- when sugars differ from one another
only in configuration about one
carbon atom
Ex. Glucose and mannose; glucose and
galactose

Enantiomers

D and L isomers

Enantiomers

Optical Activity
- the ability of a solution to rotate the plane
of plane-polarized light towards the right
or
towards the left.
- to the right or dextrorotatory: ( + )
- to the left or levorotatory: ( - )
-gives rise to 2 structures that are mirror
image to each other called enantiomers

Pyranose and Furanose Ring

Structure
- results from general reaction between
aldehydes and alcohols forming
hemiacetals or between ketones and
alcohols forming hemiketal
- only aldoses with 5 or more carbon
atoms can form pyranose rings
- OH at C5 reacts with aldehyde grp at C1
- results in asymmetry at C1 resulting in a and B
stereoisomers of D-glucose

Pyranose and Furanose Structures

a and B-stereoisomerism

Glucose

Glycosidic bond
- monosacharides joined covalently by oglycosidic bond

Glycosidic Bond
Joins together 2 monosaccharides through a reaction
between the anomeric carbon of one unit and a hydroxyl
group of another.
Nomenclature:
- monosaccharide on the left: unit where
the anomeric carbon is involved
- O precedes the name of the first
monosaccharide
- a or B configuration of the first unit
- furanosyl or pyranosyl
- ( no. of C atom of first unit no. of C atom of 2nd unit)

Disaccharides

Disaccharides

Disaccharides

Polysaccharides

Glycogen

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