Escherichia coli K-12 substr. MG1655 Compound: thiamine diphosphate

Synonyms: thiamin diphosphate, TDP, thiamine pyrophosphate, TPP, thiamin-PPi, thiamin pyrophosphate, thiamine-PPi, ThPP

Summary from MetaCyc:
Thiamin(e), also known as vitamin B1, is known to play a fundamental role in energy metabolism. Its discovery followed from the original early research on the anti-beriberi factor found in rice bran. Beriberi, a neurological disease, was particularly prevalent in Asia, where the refining of rice resulted in the removal of the thiamin-containing husk [Begley96]. The anti-beriberi substance was crystallized from rice polishings by Jansen and Donath in 1926 [Jansen26]. The structure and synthesis of thiamine were reported by Williams [Williams38]. The compound was named thiamine when it was believed to be an amine. When it became clear that it is not an amine, the 'e' was dropped, and the name was changed to thiamin [Lonsdale06].

Thiamin diphosphate is the active form of the vitamin in vivo.

Chemical Formula: C12H16N4O7P2S

Molecular Weight: 422.29 Daltons

Monoisotopic Molecular Weight: 425.04496769540003 Daltons

thiamine diphosphate compound structure

SMILES: CC1([N+](=CSC(CCOP([O-])(=O)OP([O-])(=O)[O-])=1)CC2(C=NC(C)=NC(N)=2))

InChI: 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-2


Unification Links: CAS:154-87-0, ChEBI:58937, ChemSpider:13082024, HMDB:HMDB01372, IAF1260:33732, KEGG:C00068, PubChem:15938963

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -390.53

Reactions known to produce the compound:

thiamine diphosphate biosynthesis I (E. coli) , thiamine salvage II :
thiamine phosphate + ATP → thiamine diphosphate + ADP

Reactions known to both consume and produce the compound:

Not in pathways:
thiamine diphosphate + H2O ↔ thiamine phosphate + phosphate + H+
thiamine diphosphate + ADP + H+ ↔ adenosine thiamine triphosphate + phosphate

In Reactions of unknown directionality:

Not in pathways:
2-(α-hydroxyethyl)thiamine diphosphate + a [pyruvate dehydrogenase E2 protein] N6-lipoyl-L-lysine = a [pyruvate dehydrogenase E2 protein] N6-S-acetyldihydrolipoyl-L-lysine + thiamine diphosphate
pyruvate + thiamine diphosphate + H+ = 2-(α-hydroxyethyl)thiamine diphosphate + CO2

In Transport reactions:
thiamine diphosphate + phosphate + n H+[periplasm] → thiamine triphosphate + H2O + n H+[cytosol]

Enzymes inhibited by thiamine diphosphate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: ITPase [Zheng05a]

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: 2-oxoglutarate decarboxylase, transketolase, transketolase, pyruvate dehydrogenase, pyruvate:ferredoxin oxidoreductase, glyoxylate carboligase, 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase, pyruvate oxidase, acetohydroxybutanoate synthase, acetohydroxybutanoate synthase, acetohydroxybutanoate synthase, acetolactate synthase, acetolactate synthase, acetolactate synthase, 2-oxoglutarate dehydrogenase, pyruvate:flavodoxin oxidoreductase, 1-deoxyxylulose-5-phosphate synthase

Regulated Transcription Units (2 total):


Transcription-unit diagram

Transcription-unit diagram


Begley96: Begley, T.P. (1996). "The biosynthesis and degradation of thiamin (vitamin B1)." Natural products report.

Jansen26: Jansen, B.C.T., Donath, W.F. (1926). "On the isolation of the anti-beriberi vitamin." Proc K Acad Wet Amsterdam 29: 1390.

Lonsdale06: Lonsdale D (2006). "A review of the biochemistry, metabolism and clinical benefits of thiamin(e) and its derivatives." Evid Based Complement Alternat Med 3(1);49-59. PMID: 16550223

Williams38: Williams, R.R. (1938). "Chemistry of thiamine (vitamin B1)." JAMA 110: 727-31.

Zheng05a: Zheng J, Singh VK, Jia Z (2005). "Identification of an ITPase/XTPase in Escherichia coli by structural and biochemical analysis." Structure 13(10);1511-20. PMID: 16216582

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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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