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CARBOHYDRATES M#2.3.1
Doc Asdala| Sept. 20, 2017
OUTLINE Types of Isomerism
Legend:
Remember Prev ious
Lecturer Book Trans Com
(Exams) Trans 2. Positional isomers
- Differ in the position of the functional groups with
respect to main chain
- Same functional group, but different position
I. ISOMERS
Compounds that have the same chemical formula but
different spatial or structural arrangement.
e.g. Fructose, glucose, mannose and galactose
Carbohydrate isomers that differ in configuration
around only one specific carbon atom are defined as
epimers of each other.
III. CARBOHYDRATES
Also known as Saccharides
- Racemases – enzyme that are able to inconvert D Most abundant organic compounds in nature
and L isomers. Molecular compounds containing 3 elements: carbon,
hydrogen, and oxygen (CHO)
2. Diasteriomer Source and storage form of energy as well as structural
- Stereoisomers that are NOT mirror images of each component of cell membrane
other
E.g. Glucose, sucrose, starch, and cellulose
- Cis and Trans isomers are also called Geometric
The predominant carbohydrates encountered in the
Isomers
body are structurally related to the aldotriose
- Cis-isomers have 2 groups on the same direction
glyceraldehyde and to the ketotriose dihydroxyacetone
- Trans-isomers have point in opposite direction
Glyceraldehyde
2. Disaccharides
Contain 2 monosaccharide units
Glycosidic linkage – bond between two
monosaccharide
Optically active
3. Oligosaccharides
3-10 monosaccharide units
e.g. Raffinose and Stachyose (found in beans and
legumes)
1. D- isomers- (Dextro “right side” in Latin) the OH group of **you can also use H as marker wherein α anomer H is
the highest numbered chiral carbon is found at the right at akyat and β anomers the H is at baba.
2. L- isomers- (Levo “left side” in Latin) the OH group of the
highest numbered chiral carbon is found at the left
C.Maltose
Also called as malt sugar
Formed by an α (1-4) between 2 d-glucose units
Reducing sugar since there is a free anomeric carbon
on one of the glucose that can open to give an aldehyde
A. Sucrose
Most abundant disaccharide VI. Polysaccharides
Formed by a α,β (1-2) glycosidic linkage between a D- Polysugars or sugars formed by a large number of
glucose and β-D-fructose monosaccharide units
Non-reducing sugar since the glycosidic bond was Can be linear or have branches of monosaccharide
formed at both anomeric carbons. No free aldehyde units
group can reduce the dye/reagent
A. Important polysaccharides
- that differs in the type of glycosidic bonds and the degree of
branching but composed of glucose units
1. Starch
- Primary storage polysaccharide in plants (roots and
stem)
- Most common forms of starch are Amylose and
Amylopectin. Most starches contain 20 to 30%
Amylose and 75-80% Amylopectin
- The breakdown of these polysaccharides will
produce only D-glucose monosaccharides
a. Amylose
Linear or chain type and can contain as many as 4,000
D-glucose units connected by α- 1,4 glycosidic
B. Lactose
linkages
Also called as milk sugar as it is found in high b. Amylopectin
percentage of dairy milk Branched-chain and can contain thousands of D-
Formed by a β (1-4) glycosidic linkage between β-D- glucose upon hydrolysis. Linear portion are joined by
galactose and D-glucose α- 1,4 glycosidic linkages while branches are formed
Reducing sugar since there is a free anomeric carbon by α- 1,6 glycosidic linkages. Branching usually
(of glucose) that can open to give an aldehyde occurs every 30 glucose subunits
5. Glycosaminoglycans
2. Glycogen - Also called as mucopolysaccharides since it is a
- Major glucose storage molecules in animals complex of carbohydrates containing amino sugars
- Structurally similar to amylopectin in starches but and uronic acids
are highly branched - Precursor of proteoglycans (GAGs attached to
protein) which is an integral part of the ground
substance of connective tissues.
3. Cellulose
- Most abundant organic molecule in nature
- Long, unbranched, D-glucose polymer linked by β
1-4 glycosidic linkages
- Animals can’t hydrolyze cellulose and fibers due to
the lack of enzyme-cellulase
4. Inulin
- Dietary fibers from plants which on hydrolysis,
yields mainly fructose units but are not hydrolyzed
by intestinal enzymes
- Can be used to determine Glomerular Filtration Rate
(GFR)
6. Glycoproteins
- Also called as mucorproteins which can contain
either branched or unbranched oligosaccharides
which plays a role in maintaining the integrity of cell
membranes.
- Carbohydrates that are commonly found in
glycoproteins are:
- N-acetylclucosamine (GlcNAc) and N-
acetylgalactosamine (GalNaC) which are acetyl
hexosamines
- The carbohydrate can either be attached via O-
linkage (hydroxyl group) or via N-linkage (amino
group)
References:
1. Doc Asdala’s powerpoint
2. Lippincott’s Illustrated Reviews
3. Harper’s Illustrated Biochemistry by Murray et. al