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Biochemistry of Amino Acids - Biochemistry of Proteins - Portrait of Allosteric Protein - Enzymes
Biochemistry of Amino Acids - Biochemistry of Proteins - Portrait of Allosteric Protein - Enzymes
Biochemistry of Amino Acids - Biochemistry of Proteins - Portrait of Allosteric Protein - Enzymes
• Introduction
• Biochemistry of Amino Acids
• Biochemistry of Proteins
• Portrait of Allosteric Protein
• Enzymes
Outline
• Biochemistry of Carbohydrates
• Glycoproteins and Glycosaminoglycan
• Biochemistry of Lipids
• Biological Membranes
• Bioenergetics and Oxidative
Phosphorylation
• Basic Concepts of Metabolism
Carbohydrate Biochemistry
Objectives
• Recognize the features and functions of different
classes of “carbohydrates”
• Understand the concept of asymmetric carbons and other
diastereoisomers, epimers and enantiomers and anomers
• Recognize the structure of glucose and its relationship
with other monosaccharides
• Understand the different reactions of monosaccharide
• Understand the nature of glycosidic bond and recognize
the structure of the common disaccharides
• Recognize the different types and classes of
polysaccharides
• Understand the basic differences between amylose and
cellulose
*Functions of Carbohydrates
* Classification of CHO
- Monosaccharides
- aldoses and ketoses
* Structure of Monosaccharides
-isomers, epimers and enantiomers
-cyclic structure, hemiacetal and hemiketal
*Reactions of monosaccharides
* Derivatives of Hexoses
-amino sugars
-acidic sugars
-Glycosides
* Disaccharides
-disaccharide formation and hydrolysis
-nomenclature of disaccharides
-glycosides
* Polysaccharides (Glycans)
-homo and hetero polysaccharides
-Storage polysaccharides; starch & Glycogen
-Structural polysaccharides, cellulose & chitin
Biochemistry of Carbohydrate
Carbohydrates (CHO) are the most abundant biomolecules in nature
Functions of Carbohydrates
1. Energy source for plants and animals
2. Source of carbon in metabolic processes
3. Storage form of energy
4. Structural elements of cells and tissues
5. Some CHO participate in recognition and adhesion between cells and mediate
some forms of inter cellular communications
Classes of Saccharides
Monosaccharides
= single polyhydroxy aldehyde or ketone unit,
(eg. 6-carbon glucose, most abundant in nature)
Oligosaccharides
= short chain of 2- ~20 monosaccharides joined by “glycosidic bonds”
(eg. disaccharide sucrose = glucose-fructose)
- oligosaccharides > 3 residues are usually joined to protein or lipid
in “glycoconjugates”
Polysaccharides
- chains > ~ 20 to 1000’s of monosaccharides in length
- linear: eg. cellulose (glucose)n or chitin (N-acetylglucosamine)n
- branched: eg. glycogen & starch (glucose)
- depending on the sugar residues in a polysaccharide and the linkages
between them, polysaccharides can have very different biological roles
Monosaccharides
- Backbone = un-branched carbon chains in which all C atoms are linked by single bonds
- Colorless, crystalline, solid freely soluble in water, insoluble in organic solvents
- If it has keto group as the most oxidized functional group = Ketose
- If it has aldehyde group as the most oxidized functional group = aldose
According to the number of carbon atoms
- 3 C = triose, 4 C = tetrose, 5 C = pentose, 6 C = hexose (eg. aldo- or ketohexoses)
Aldotriose ketotriose...
Monosaccharides have asymmetric centers
- All monosaccharides (except dihydroxyacetone) have one or more asymmetric carbons
- eg. glyceraldehyde: middle C is a chiral center, so molecule has 2 different optical isomers
or enantiomers (= stereoisomers that are non-super imposable mirror images of one another)
By convention, one enantiomer = the D isomer, the other is L,
Configurations of glyceraldehyde:
D and L configurations of monosaccharides
- Stereoisomers of monosaccharides > 3 C divided into 2 groups:
differ in the configuration about the chiral center most distant from the carbonyl C
In biochemistry, we use the D-L system (similar principle to the R-S system usually used in
organic, but everything is compared with glyceraldehyde
- In general, a molecule with n chiral centers can have 2n stereoisomers
IN ALDOHEXOSES, C-2, 4
C-3, C-4, AND C-5
= CHIRAL CENTERS, 5
SO 24 = 16 POSSIBLE 6
ALDOHEXOSES: MIRROR
8 D AND 8 L
The D and L designation of sugars with n > 3 are taken from the
chiral carbon furthest from the carbonyl carbon.
Conformational isomers:
Formation of the two cyclic forms of D-Glucose
α-D- Mannose α -D Galactose
Interconversion between anomers
Anomers: Isomeric forms of monosaccharides that differ only in their
configuration at the anomeric carbon.
Mutarotation: The interconversion of a and b anomers of the monosaccharide
Glycosidic bond- bond between the anomeric carbon of a sugar and an alcohol
(can be another sugar) or amine (a base) through an O- or N- linkage.
Typical Aglycone
- Purines, Pyrimrdines fo form Nucleotides
- Aromatic rings (steroids)
- Proteins to form glycoproteins, the polypeptide is joined to the sugar moiety
via Asparagine to form N-glycoside and via serine to form O-glycosides
- lipids to form and glycolipids
Complex carbohydrates
N-glycoside
O-glycosides
Joining of sugars via glycosidic bonds
- Reaction = formation of an
acetal from a hemiacetal (eg. C-
1 of gluco pyranose) and an
alcohol (-OH group on C-4 of
second glucopyranose molecule)
Joining of sugars via glycosidic bonds
- When an anomeric carbon participates in a glycosidic bond, it cannot exist in linear form,
and can no longer act as a reducing sugar (ie. it can’t reduce Cu2+)
- The end of a di- or polysaccharide chain with a free anomeric carbon (ie. not involved in a
glycosidic bond) = the “reducing end”
REDUCING
END
NON-
REDUCING
END
α OR β
b/c
MUTAROTATION
a
The name describes the sugar
with its reducing end
α (14)
In β(14)-linked polysaccharides,
each residue is rotated 180° relative
to its neighbors. The intra-chain H-bonds can form
between ring O and the -OH of C-3 on
adjacent glucoses:
CH3
O=C
H- N
|
O
O
O
CH2OH
The End