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- Name help_outline 2-[(2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate Identifier CHEBI:62899 Charge -3 Formula C7H7NO6PS InChIKeyhelp_outline PQMCQNOVNFNPFJ-HYIMLASBSA-K SMILEShelp_outline CC1=N[C@H](SC\1=C/COP([O-])([O-])=O)C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate Identifier CHEBI:62890 Charge -3 Formula C7H7NO6PS InChIKeyhelp_outline XWECMAHAKFWYNV-UHFFFAOYSA-K SMILEShelp_outline Cc1nc(sc1CCOP([O-])([O-])=O)C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:31459 | RHEA:31460 | RHEA:31461 | RHEA:31462 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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A missing enzyme in thiamin thiazole biosynthesis: identification of TenI as a thiazole tautomerase.
Hazra A.B., Han Y., Chatterjee A., Zhang Y., Lai R.Y., Ealick S.E., Begley T.P.
In many bacteria tenI is found clustered with genes involved in thiamin thiazole biosynthesis. However, while TenI shows high sequence similarity with thiamin phosphate synthase, the purified protein has no thiamin phosphate synthase activity, and the role of this enzyme in thiamin biosynthesis re ... >> More
In many bacteria tenI is found clustered with genes involved in thiamin thiazole biosynthesis. However, while TenI shows high sequence similarity with thiamin phosphate synthase, the purified protein has no thiamin phosphate synthase activity, and the role of this enzyme in thiamin biosynthesis remains unknown. In this contribution, we identify the function of TenI as a thiazole tautomerase, describe the structure of the enzyme complexed with its reaction product, identify the substrates phosphate and histidine 122 as the acid/base residues involved in catalysis, and propose a mechanism for the reaction. The identification of the function of TenI completes the identification of all of the enzymes needed for thiamin biosynthesis by the major bacterial pathway. << Less
J. Am. Chem. Soc. 133:9311-9319(2011) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.