Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

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

Synonyms: thiamine 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

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

InChIKey: InChIKey=AYEKOFBPNLCAJY-UHFFFAOYSA-L

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

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

Reactions known to produce the compound:

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

Reactions known to both consume and produce the compound:

Not in pathways:
thiamin diphosphate + H2O ↔ thiamin phosphate + phosphate + H+
thiamin 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 + thiamin diphosphate
pyruvate + thiamin diphosphate + H+ = 2-(α-hydroxyethyl)thiamine diphosphate + CO2

In Transport reactions:
thiamin diphosphate + phosphate + n H+[periplasmic space] → thiamin triphosphate + H2O + n H+[cytosol]

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

Inhibitor (Competitive) of: ITPase [Zheng05]

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): ?

Notes:


References

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.

Zheng05: 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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 18.5 on Wed Nov 26, 2014, BIOCYC13B.