|Superclasses:||Reactions Classified By Conversion Type → Simple Reactions → Chemical Reactions|
|Reactions Classified By Substrate → Small-Molecule Reactions|
EC Number: 188.8.131.52
Enzymes and Genes:
|Acremonium chrysogenum :||deacetoxycephalosporin C synthase / deacetoxycephalosporin C hydroxylase
|Streptomyces clavuligerus :||deacetoxycephalosporin C hydroxylase
In Pathway: deacetylcephalosporin C biosynthesis
The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.
Mass balance status: Balanced.
Enzyme Commission Primary Name: deacetoxycephalosporin-C hydroxylase
Enzyme Commission Synonyms: deacetylcephalosporin C synthase, 3'-methylcephem hydroxylase, DACS, DAOC hydroxylase, deacetoxycephalosporin C hydroxylase
Standard Gibbs Free Energy (ΔrG'° in kcal/mol): -119.75 [Latendresse13]
Enzyme Commission Summary:
The enzyme can also use 3-exomethylenecephalosporin C as a substrate to form deacetoxycephalosporin C, although more slowly. In Acremonium chrysogenum, the enzyme forms part of a bifunctional protein along with EC 184.108.40.206. It is a separate enzyme in Streptomyces clavuligerus.
Baker91: Baker BJ, Dotzlaf JE, Yeh WK (1991). "Deacetoxycephalosporin C hydroxylase of Streptomyces clavuligerus. Purification, characterization, bifunctionality, and evolutionary implication." J Biol Chem 266(8);5087-93. PMID: 2002049
Coque96: Coque JJ, Enguita FJ, Cardoza RE, Martin JF, Liras P (1996). "Characterization of the cefF gene of Nocardia lactamdurans encoding a 3'-methylcephem hydroxylase different from the 7-cephem hydroxylase." Appl Microbiol Biotechnol 44(5);605-9. PMID: 8703431
Ghag96: Ghag SK, Brems DN, Hassell TC, Yeh WK (1996). "Refolding and purification of Cephalosporium acremonium deacetoxycephalosporin C synthetase/hydroxylase from granules of recombinant Escherichia coli." Biotechnol Appl Biochem 24 ( Pt 2);109-19. PMID: 8865604
Lloyd04: Lloyd MD, Lipscomb SJ, Hewitson KS, Hensgens CM, Baldwin JE, Schofield CJ (2004). "Controlling the substrate selectivity of deacetoxycephalosporin/deacetylcephalosporin C synthase." J Biol Chem 279(15);15420-6. PMID: 14734549
Martin94: Martin JF, Gutierrez S, Fernandez FJ, Velasco J, Fierro F, Marcos AT, Kosalkova K (1994). "Expression of genes and processing of enzymes for the biosynthesis of penicillins and cephalosporins." Antonie Van Leeuwenhoek 65(3);227-43. PMID: 7847890
Wu05: Wu XB, Fan KQ, Wang QH, Yang KQ (2005). "C-terminus mutations of Acremonium chrysogenum deacetoxy/deacetylcephalosporin C synthase with improved activity toward penicillin analogs." FEMS Microbiol Lett 246(1);103-10. PMID: 15869968
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