Carbohydrates

Carbohydrates
■ Carbohydrate – (hydrated carbon)
■ Carbohydrates have empirical formula CnH2nOn.
■ Most abundant carbohydrate is glucose, C6H12O6.
■ Carbohydrates are made up of chains of individual monomer
components joined together to form a polymer.
■ Carbohydrates are polyhydroxy aldehydes or ketones, or
substances that yield such compounds on hydrolysis
■ Depending on the placement of the carbonyl group they may
be aldoses or ketoses.
■ For carbohydrates, the functional group is the carbonyl group
which may be either
■ Aldehyde Group (H-C=O) Keto Group (C=O)
 Classes of Carbohydrates Monosacc

■ Monosaccharides are simple sugars (a single monomer)

■ Have 3, 4, 5, 6, or 7 carbons referred to as trioses, tetroses,
pentoses, hexoses, and heptoses
■ Examples of pentoses include ribose and deoxyribose (part of
nucleic acids)
■ Examples of hexoses include glucose, fructose, and galactose;
glucose is most abundant.
 Disaccharides
■ Consist of two monosaccharide units, the two monomers are
joined by a glycosidic linkage or glycosidic bond formed when
the equivalent of a water molecule is removed from the two
monosaccharides an oxygen atom is bound to a carbon from
each monomer
■ Examples:

■ Sucrose - Table Sugar - glucose + fructose

■ Lactose - Milk Sugar - glucose + galactose
■ Maltose - Malt Sugar - glucose + glucose
 Polysaccharides
■ polysaccharides are macromolecules made of repeating
monosaccharides units linked together by glycosidic bonds
number of subunits varies, typically thousands can be
branched or unbranched some are easily broken down and
are good for energy storage (examples: starch, glycogen) some
are harder to break down and are good as structural
components (example: cellulose)
■ Polysaccharides starch is the main storage form of
carbohydrate of plants. Polymer made from α -glucose units
linked primarily between carbons 1 and 4. Plants store starches
in organelles called amyloplasts, a type of plastid
■ Polysaccharides glycogen is the main storage form of
carbohydrate of animals. Similar to starch, but very highly
branched and more water-soluble. Is NOT stored in an
organelle; mostly found in liver and muscle cells
■ Polysaccharides cellulose is the major structural component of
most plant cell walls. Polymer made from b-glucose units
linked primarily between carbons 1 and 4 (similar to starch, but
note that the b1-4 linkage makes a huge difference)
 Oligosaccharides
■ These are compound sugars that yield 2 to 10 molecules of
the same or different monosaccharides on hydrolysis.
Accordingly an oligosaccharides yields 2 molecules of
monosaccharides is designated as disaccharide, and the one
yielding 3 molecules as trisaccharides and so on.
■ Trisaccharides: Rhamninose, Raffinose, Rabinose
■ Tetrasaccharides: Stachyose, Scorodose
■ Pentasaccharides: Verbascose
 The Stereochemistry of Carbohydrates
■ Stereochemistry refers to the 3-dimensional properties and
reactions of molecules.
■ Stereoisomers – compounds with the same connectivity,
different arrangement in space
■ Enantiomers – stereoisomers that are non- superimposible
mirror images; only properties that differ are direction (+ or -)
of optical rotation. Optical isomers (enantiomers) differ from
each other in the disposition of the various atoms or groups of
atoms in space around the asymmetric carbon atom. These
are infact the mirror image of each other. These may also be
likened to left and right handed gloves.
Glyceraldehyde, the simplest carbohydrate, exists in two
isomeric forms that are mirror images of each other. One form
in which H atom at carbon 2 is projected to the left side and OH
group to the right is designated as D-form and the other form
where H atom is projected to the right side and OH group to
the left is called as L-form.
 Isomers and Epimers
■ Isomers - Compounds having same
chemical formula but different
structural formula
■ The No. of isomers depends on the
No. of asymmetric C 12.
■ Aldo-Keto Isomers - Example:
Glucose (Aldose) and Fructose
(Ketose)
■ Epimers CHO dimers that differ in
configuration around only one
specific carbon atom
■ Glucose and galactose – C4
■ Glucose and Mannose – C2
■ Galactose and mannose are not
epimers
 Enantiomers (D and L forms)
■ Structures that are mirror images
of each other are designated as D
and L sugars based on the
position of –OH group on the
asymmetric carbon farthest from
the carbonyl carbon
■ Majority of sugars in humans are
D-sugars Enantiomers (D and L
Forms)
 α- and β-Forms
■ Cyclization of Monosaccharides
Monosaccharides with 5 or more
carbon are predominantly found
in the ring
■ The aldehyde or ketone group
reacts with the –OH group on
the same sugar
■ Cyclization creates an anomeric
carbon (former carbonyl carbon)
generating the α and β
configurations.
 Functions of Carbohydrates
■ Carbohydrates provides energy and regulation of blood
glucose.
■ It will prevent the degradation of skeletal muscle and other
tissues such as the heart, liver, and kidneys.
■ It prevent the breakdown of proteins for energy.
■ Carbohydrates also help with fat metabolism. If the body has
enough energy for its immediate needs, it stores extra energy
as fat.
■ Carbohydrates are an important component of many
industries like textile, paper and breweries.
■ Detoxification of physiological importance is carried out to
some extent with carbohydrate derivatives.
■ Agar is polysaccharide used in culture media, laxative and
food.
■ Carbohydrates form a part of genetic material like DNA and
RNA in the form of deoxyribose and ribose sugars.
■ Hyaluronic acid found in between joints acts as synovial fluid
and provides frictionless movement. They help make up the
body mass by being included in all the parts of the cell and
tissues.
■ Adequate storage of hepatic glycogen helps in detoxifying a
normal liver.
■ They form components of bio-molecules which have a key role in blood
clotting, immunity, fertilization etc.
■ Carbohydrates is basically the main fibre of the diet or provide the bulk
fibre for better digestion. Carbohydrates help clear gut and prevent
constipation.
■ Starch is the form the food is stored in plants.
■ It provides sweetness to foods.
■ Pectine and Hemicellulose are the structural carbohydrate in plant cell
walls. It plays important roles in cellular recognition processes.
■ Chitin forms the cell wall of fungi and the outer schelitone of insects.
■ Murine is a structural carbohydrate in bacterial cell wall.