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MetaCyc Reaction: 1.14.11.26

Superclasses: Reactions Classified By Conversion TypeSimple ReactionsChemical Reactions
Reactions Classified By SubstrateSmall-Molecule Reactions

EC Number: 1.14.11.26

Enzymes and Genes:

Acremonium chrysogenum: deacetoxycephalosporin C synthase / deacetoxycephalosporin C hydroxylaseInferred from experiment: CEFEF
Streptomyces clavuligerus: deacetoxycephalosporin C hydroxylaseInferred from experiment: cefF

In Pathway: deacetylcephalosporin C biosynthesis

The direction shown, i.e. which substrates are on the left and right sides, 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): -119.75Inferred by computational analysis [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 1.14.20.1. It is a separate enzyme in Streptomyces clavuligerus.

Citations: [Martin94, Wu05, Lloyd04, Ghag96, Coque96, Baker91, Dotzlaf87]

Gene-Reaction Schematic

Gene-Reaction Schematic

Unification Links: KEGG:R05229, Rhea:16805

Relationship Links: BRENDA:EC:1.14.11.26, ENZYME:EC:1.14.11.26, IUBMB-ExplorEnz:EC:1.14.11.26


References

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

Dotzlaf87: Dotzlaf JE, Yeh WK (1987). "Copurification and characterization of deacetoxycephalosporin C synthetase/hydroxylase from Cephalosporium acremonium." J Bacteriol 169(4);1611-8. PMID: 3558321

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

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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