Showing metabocard for Thiamine pyrophosphate (MMDBc0029635)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:35:31 UTC
Update Date2022-08-31 14:15:39 UTC
MiMeDB IDMMDBc0029635
Metabolite Identification
Common NameThiamine pyrophosphate
DescriptionThiamine pyrophosphate (TPP) is the active form of thiamine, and it serves as a cofactor for several enzymes involved primarily in carbohydrate catabolism. The enzymes are important in the biosynthesis of a number of cell constituents and for the production of reducing equivalents used in oxidant stress defenses and in biosyntheses and for synthesis of pentoses used as nucleic acid precursors. The chemical structure of TPP is that of an aromatic methylaminopyrimidine ring, linked via a methylene bridge to a methylthiazolium ring with a pyrophosphate group attached to a hydroxyethyl side chain. In non-enzymatic model studies it has been demonstrated that the thiazolium ring can catalyse reactions which are similar to those of TPP-dependent enzymes but several orders of magnitude slower. Using infrared and NMR spectrophotometry it has been shown that the dissociation of the proton from C2 of the thiazolium ring is necessary for catalysis; the abstraction of the proton leads to the formation of a carbanion (ylid) with the potential for a nucleophilic attack on the carbonyl group of the substrate. In all TPP-dependent enzymes the abstraction of the proton from the C2 atom is the first step in catalysis, which is followed by a nucleophilic attack of this carbanion on the substrate. Subsequent cleavage of a C-C bond releases the first product with formation of a second carbanion (2-greek small letter alpha-carbanion or enamine). The formation of this 2-greek small letter alpha-carbanion is the second feature of TPP catalysis common to all TPP-dependent enzymes. Depending on the enzyme and the substrate(s), the reaction intermediates and products differ. Methyl-branched fatty acids, as phytanic acid, undergo peroxisomal beta-oxidation in which they are shortened by 1 carbon atom. This process includes four steps: activation, 2-hydroxylation, thiamine pyrophosphate dependent cleavage and aldehyde dehydrogenation. In the third step, 2-hydroxy-3-methylacyl-CoA is cleaved in the peroxisomal matrix by 2-hydroxyphytanoyl-CoA lyase (2-HPCL), which uses thiamine pyrophosphate (TPP) as cofactor. (PMID: 12694175 , 11899071 , 9924800 )
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x000055b769e79980>

Not Available

3D MOL for #<Metabolite:0x000055b769e79980>

Not Available

3D SDF for #<Metabolite:0x000055b769e79980>

Not Available

3D-SDF for #<Metabolite:0x000055b769e79980>

Not Available

PDB for #<Metabolite:0x000055b769e79980>

Not Available

3D PDB for #<Metabolite:0x000055b769e79980>

Not Available

SMILES for #<Metabolite:0x000055b769e79980>

Not Available

INCHI for #<Metabolite:0x000055b769e79980>

Not Available
SynonymsNot Available
Chemical FormulaC12H19N4O7P2S
Average Molecular Weight425.314
Monoisotopic Molecular Weight425.044967696
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number154-87-0
SMILESNot Available
InChI Identifier
InChI=1S/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)/p+1
InChI KeyAYEKOFBPNLCAJY-UHFFFAOYSA-O