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Cofactors
Cofactors
Cofactors are organic or inorganic molecules that are required for the activity of a certain conjugated enzymes Apoenzyme = enzyme (-) cofactor
Coenzymes
Cosubstrates- altered in rxn and regenerated to original structure in subsequent rxn - disassociated from active site - shuttle chemical groups among different enzyme rxns. Prosthetic groups- remains bound to enzyme - must return to original form Both cosubstrates and prosthetic groups supply reactive groups not present on amino acid side chains
Coenzymes
Metabolite coenzymes synthesized from common metabolites Nucleoside triphosphates (ATP) can donate phosphates, pyrophosphates, adenosyl grroups S-adenosylmethionine (SAM) donates methyl groups Nucleotide sugars (uridine diphosphate glucose = UDP-glucose) - transfer sugars in carbohydrate metabolism
Vitamin Ascorbic acid (C) Niacin Riboflavin (B2) Thiamin (B1) Pyridoxal (B6) Biotin Folate Cobalamin (B12) Vitamin A Vitamin K Pantothenate (B3)
Vitamins
Coenzyme not a coenzyme NAD(P)+/NAD(P)H FMN & FAD Thiamin-pyrophosphate Pyridoxal phosphate Biotin Tetrahydrafolate adenosyl-and methylcobalamin Retinal Vitamin K Coenzyme A
Deficiencies lead to pellagra (dermatitis, diarrhea, dementia) Required in relatively high amounts compared to other vitamins Not true enzyme because can be synthesized from tryptophan in the liver
Nicotinamide Coenzymes
NICOTINAMIDE MONOPHOSPHATE
O C NH2
O C OH O C NH2 N NICOTINAMIDE
N H2 C O PO2O OH OH NH2 O
H
ADENOSINE MONOPHOSPHATE
PO2O CH2 O
N N N
O C NH2
O C NH2
N
R
OH OH(OPO3)
N
R REDUCED
OXIDIZED
Serve as cofactors in oxidation/reduction reactions Act as co-substrates for dehydrogenases Reduction of NAD+/NADP+ and oxidation of NADH/NADPH occurs 2 e- at a time. Function in hydride ion transfer Rxns forming NADH/NADPH are catabolic NADH is coupled with ATP production in mitochondria NADPH is an impt reducing agent in biosynthetic reactions Reduced forms (NADH/NADPH) absorb light at 340 nm, oxidized forms (NAD+/NADP+) do not
+ NAD
+ NADP
Riboflavin (B2)
Water soluble vitamin Severe deficiencies lead to growth retardation, reproductive problems and neural degeneration Meat, dairy products and dark green vegetables, legumes and grains are good sources
FMN/FAD
semiquinone form
Thiamin
Thiamin is the first Vitamin discovered (Vital amine = Vitamin) Deficiencies lead to disease called Beriberi (neurological disorders, heart problems, anorexia) Beriberi prevealent in undeveloped countries where polished grains make up the majority of the diet. Associated with alcohol related disorders (Wernickes-Korskofff syndrome memory loss, unstable walk)
Thiamin pyrophosphate
Serves as a cofactor in decarboxylation rxn of keto acids Also functions as a prosthetic group in transketolases (catalyze the transfer of two carbon units in carbohydrate metabolism)
Pyridoxal
OH H2C HOH2C O HOH2C HC O HOH2C O H2C O NH3
N H PYRIDOXINE
CH3
N H PYRIDOXAL
CH3
N H
CH3
PRYIDOXAMINE
NH3
CH3
PYRIDOXAL-PHOSPHATE
Important in amino acid metabolism
Bound to enzyme as a Schiff base thru rxn with lysine O
- H2O R C H + NH2 AMINE R2 + H2O ALDEHYDE R C H N R2 SCHIFF BASE
PLP functions in transamination, decarboxylation, racemization, isomerization, side-chain elimination rxns involving amino acids