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S.S. Jain Subodh Girls P.G. College, Sanganer, Jaipur: Department of CHEMISTRY M.Sc. (Final)
S.S. Jain Subodh Girls P.G. College, Sanganer, Jaipur: Department of CHEMISTRY M.Sc. (Final)
DEPARTMENT OF
CHEMISTRY M.Sc. (Final)
EXAMPLES OF COENZYME:
(1) Coenzyme A
(2) NAD+
(3) NADP+
(4) B12
(5) Lipoic acid
(1) COENZYME A
Vitamin derived coenzyme
Also known as “acetyl co-A” naturally derives
from vitamin B5 (Pantothenate) which is found
in foods such as meat, vegetable, cereal
grains, legumes, eggs, and milk. In humans
and most living organisms pantothenate is an
essential vitamin that has variety of functions.
In some plants and bacteria (Escherichia coli)
pantothenate can be synthesized and is
therefore not considered essential. These
bacteria synthesize pantothenate from amino
acids, aspartate and a metabolite in valine
biosynthesis.
In all living organisms, COENZYME-A is
synthesized in five step process that requires
four molecules of ATP, pantothenate, and
cysteine.
FOOD INTAKE
VITAMIN B5
COENZYME-A
Regulation Acetyl group carrier
ACETYL-CO-A
LIPID METABOLISM TCA CYCLE FATTY ACID
SYNTHESIS & OXIDATION
CO2 ENERGY
In its acetyl form, coenzyme A is highly
versatile molecule serving metabolic
functions in both the anabolic and catabolic
pathways. Acetyl CO-A is utilised in the post
transational regulations and allosteric
regulation of pyruvate dehydrogenase and
carboxylase to maintain and support the
partition of pyruvate synthesis and degration.
FUNCTIONS -
(1)Fatty acid synthesis
(2)Energy production
(3)Regulation
Its responsible for initiating production of
fatty acids within cells (Fatty acid forms the
phospholipid bilayer that comprises cell
membrane). Coenzyme A also initiates the
citric acid cycle resulting in formation of ATP
(oxidation of pyruvate in citric acid cycle)
‘STRUCTURE OF COENZYME-A’
Formula - C21H36N7O16P3S
NH2
N
N
O O H3C CH3 O O N
HS O P O P O O
NH NH O- O+
OH
O OH
O P O-
O-
+
(2) NAD
NICOTINAMIDE ADENINE DINUCLEOTIDE
Are derivative of nitramin “nicin” which is nocotin
amide or nicotinic acid (pyridine 3 carboxylic acid)
NAD+ represents the oxidised form and NADH
represents the reduced form
NAD+ functions as coenzyme of an oxidoreductase
collectively called pyridine linked dehydrogenase they
are loosely bound and leave the enzyme in changed
form at the end of the reaction.
Pyridine linked dehydrogenaser – some
dehydrogenases are specific for NAD and other for
NADP, some function with either coenzyme.
COOH CONH2
N N
NICOTINIC ACID NICOTINAMIDE
NAD+ LINKED – D-B-hydroxyl butyrate,
glyceraldehyde-3 phosphate, dihydroglucamide
α,β hydroxyl co-A, ethanol cactate, glycerol-3-
phosphate & α-h-malate.
MECHANISM -
This coenzyme function as an intermediate in
transfer of 2e- between an electron donor and an
acceptor in catalytic cycle. The donor and
acceptor need to be involve in the same metallic
pathway. It acts as electron acceptor during the
enzymatic removal of hydrogen atom from
specific substrate as hydroxide ion to the
nocotinamide portion of the oxidised form to
these co-enzymes. The other hydrogen atom from
the substrate become as H+ ion thus the reduced
form of these nucleotide NADH behave as
common pool of electron that arise from many
oxidative reaction and can be used for many
reductive reactions. So we can say that the
reduction NAD+ to NADH requires 2 reducing
equivalents per molecule, one electron and one
hydrogen atom which regards as H- ion add to the
pyridine ring of nicotinamide.
The reaction mechanism involves-
H
R-N+ H H C R-N
H
CONH2
H NAD+
CH3 CH Q + R N+ N
OH CONH 2
DENTE RATE ETHANOL
O
H+ + R N+ H + H 2C
CONH2 C O
NAO
+
STRUCTURE OF NAD
O N +NICOTINAMIDE
P O CH O conh2
2
OH OH ADEMINE
NH 2 N
N
N
θ-RIBASE
P O CH
3 O
O
OH OH
NADP (NICOTINAMIDE
+
ADENINE DINUCLEOTIDE
PHOSPHATE) C H N O P
21 29 7 17 3
O P O
O N+
OH OH
O NH2
N N
O P O O N N
O-
OH O
O P O-
O-
(4) VITAMIN B12
Vitamin B12 is an important cobalt complex which
was isolated from liver after it was found that
earing large quantities of raw liver was an
effective treatment for pernicious anaemia.
Only vitamin known to contain a metal
The term vitamin B12 to cyanocobalmin
It’s an coenzyme and serve as prosthetic group
which is tightly bound to several enzymes in the
body
It is called Biological Grignard reagent
The following are the important structural
features of this vitamin –
(1) A cobalt (III) ion
(2) A macro cyclic ligand called the corming
which bears various substituents
(3) A complex organic portion consisting of a
phosphate group , a sugar and a organic
base the latter being coordinated to the
cobalt atom
(4) Co(III) is octahedrally bonded by four N-
atoms of the coring group, the organic base
and the sixth ligand X
X=CN Cyano cobalmin
X=H2O Aqua cobalmin
X=CH3 Methyl cobalmin
X=5’deoxy adenosyl Coenzyme B12
The cobamins can be reduced from CO(III) to
CO(II) and CO(I) in neutral and alkaline solution
both in laboratory and in the living body. The
CO(III) complex is strongly reducing.
Methyl cobalmin (x=ch3) is responsible for the
environment conversion of Hg (II) to toxic CH3Hg
through methane producing bacteria. Similarly it
can transfer methyl groups of (II) Pt. (II) and
(5) LIPOIC ACID
Lipoic acid is sulphur containing fatty acid found in
liver in two form which are as follows
(1). COOH
3
S1 S2
Cyclic disulphide lipoic acid
(2). COOH
SH SH