Thiamine pyrophosphate

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Thiamine pyrophosphate

IUPAC name	2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate
Other names	Thiamine diphosphate
Identifiers
CAS number	[154-87-0]
PubChem	1132
MeSH	Thiamine+pyrophosphate
SMILES	[n+]1(c(c(CCO[P@@](OP(O)(O)=O)(O)=O)sc1)C)Cc1c(nc(C)nc1)N.[ClH-]
Properties
Molecular formula	C12H19N4O7P2S+
Molar mass	425.316
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Thiamine pyrophosphate (TPP) or thiamine diphosphate (ThDP) is a thiamine derivative which is cleaved by thiamine pyrophosphatase. Thiamine phyrophosphate is the active form of thiamine (vitamin B1).^[1]

ThDP is a prosthetic group in many enzymes, such as:

Pyruvate dehydrogenase complex
Pyruvate decarboxylase complex in ethanol fermentation
Alpha-ketoglutarate dehydrogenase complex
Branched-chain amino acid dehydrogenase complex
2-hydroxyphytanoyl-CoA lyase
Transketolase

v • d • e Types of enzyme cofactors

Coenzymes	vitamins: NAD⁺ (B3) - NADP⁺ (B3) - Coenzyme A (B5) - Tetrahydrofolic acid (B9)/Dihydrofolic acid/5,10-Methylenetetrahydrofolate - Menaquinone (K) - Ascorbic acid (C) - Coenzyme F420 Adenosine triphosphate - S-Adenosyl methionine - 3'-Phosphoadenosine-5'-phosphosulfate - Coenzyme Q - Tetrahydrobiopterin - Cytidine triphosphate - Glutathione - Coenzyme M - Coenzyme B - Methanofuran - Tetrahydromethanopterin

Prosthetic groups: Organic group	vitamins: Thiamine pyrophosphate (B1) - Flavin mononucleotide (B2) - Flavin adenine dinucleotide (B2) - Pyridoxal phosphate (B6) - Biotin (B7) - Methylcobalamin (B12) - Cobamamide (B12) Pyrroloquinoline quinone - Heme - Molybdopterin - Lipoic acid

Prosthetic groups: Metals	Calcium - Selenium - Copper - Iron - Magnesium - Manganese - Nickel - Zinc - Molybdenum