KEGG   ENZYME: 1.14.11.26
Entry
EC 1.14.11.26               Enzyme                                 
Name
deacetoxycephalosporin-C hydroxylase;
deacetylcephalosporin C synthase;
3'-methylcephem hydroxylase;
DACS;
DAOC hydroxylase;
deacetoxycephalosporin C hydroxylase
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With 2-oxoglutarate as one donor, and incorporation of one atom of oxygen into each donor
Sysname
deacetoxycephalosporin-C,2-oxoglutarate:oxygen oxidoreductase (3-hydroxylating)
Reaction(IUBMB)
deacetoxycephalosporin C + 2-oxoglutarate + O2 = deacetylcephalosporin C + succinate + CO2 [RN:R05229]
Reaction(KEGG)
R05229
Substrate
deacetoxycephalosporin C [CPD:C06565];
2-oxoglutarate [CPD:C00026];
O2 [CPD:C00007]
Product
deacetylcephalosporin C [CPD:C03112];
succinate [CPD:C00042];
CO2 [CPD:C00011]
Comment
Requires iron(II). The enzyme can also use 3-exomethylenecephalosporin C as a substrate to form deacetoxycephalosporin C, although more slowly [2]. In Acremonium chrysogenum, the enzyme forms part of a bifunctional protein along with EC 1.14.20.1, deactoxycephalosporin-C synthase. It is a separate enzyme in Streptomyces clavuligerus.
History
EC 1.14.11.26 created 2005
Pathway
ec00311  Penicillin and cephalosporin biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K12745  deacetoxycephalosporin-C hydroxylase
Genes
SCLFBB341_07760
SCTSCAT_5681(cefF)
SCYSCATT_56810
AABA4R43_03240
AMYYYIM_39165(cefF)
PSUUPsuf_059670
Reference
1  [PMID:3558321]
  Authors
Dotzlaf JE, Yeh WK.
  Title
Copurification and characterization of deacetoxycephalosporin C synthetase/hydroxylase from Cephalosporium acremonium.
  Journal
J Bacteriol 169:1611-8 (1987)
DOI:10.1128/JB.169.4.1611-1618.1987
Reference
2  [PMID:2002049]
  Authors
Baker BJ, Dotzlaf JE, Yeh WK
  Title
Deacetoxycephalosporin C hydroxylase of Streptomyces clavuligerus. Purification, characterization, bifunctionality, and evolutionary implication.
  Journal
J Biol Chem 266:5087-93 (1991)
  Sequence
Reference
3  [PMID:8703431]
  Authors
Coque JJ, Enguita FJ, Cardoza RE, Martin JF, Liras P
  Title
Characterization of the cefF gene of Nocardia lactamdurans encoding a 3'-methylcephem hydroxylase different from the 7-cephem hydroxylase.
  Journal
Appl Microbiol Biotechnol 44:605-9 (1996)
DOI:10.1007/BF00172492
  Sequence
Reference
4  [PMID:8865604]
  Authors
Ghag SK, Brems DN, Hassell TC, Yeh WK.
  Title
Refolding and purification of Cephalosporium acremonium deacetoxycephalosporin C synthetase/hydroxylase from granules of recombinant Escherichia coli.
  Journal
Biotechnol Appl Biochem 24 ( Pt 2):109-19 (1996)
DOI:10.1111/j.1470-8744.1996.tb00393.x
Reference
5  [PMID:14734549]
  Authors
Lloyd MD, Lipscomb SJ, Hewitson KS, Hensgens CM, Baldwin JE, Schofield CJ.
  Title
Controlling the substrate selectivity of deacetoxycephalosporin/deacetylcephalosporin C synthase.
  Journal
J Biol Chem 279:15420-6 (2004)
DOI:10.1074/jbc.M313928200
Reference
6  [PMID:15869968]
  Authors
Wu XB, Fan KQ, Wang QH, Yang KQ.
  Title
C-terminus mutations of Acremonium chrysogenum deacetoxy/deacetylcephalosporin C synthase with improved activity toward penicillin analogs.
  Journal
FEMS Microbiol Lett 246:103-10 (2005)
DOI:10.1016/j.femsle.2005.03.043
Reference
7  [PMID:7847890]
  Authors
Martin JF, Gutierrez S, Fernandez FJ, Velasco J, Fierro F, Marcos AT, Kosalkova K.
  Title
Expression of genes and processing of enzymes for the biosynthesis of penicillins and cephalosporins.
  Journal
Antonie Van Leeuwenhoek 65:227-43 (1994)
DOI:10.1007/bf00871951
Other DBs
ExplorEnz - The Enzyme Database: 1.14.11.26
IUBMB Enzyme Nomenclature: 1.14.11.26
ExPASy - ENZYME nomenclature database: 1.14.11.26
BRENDA, the Enzyme Database: 1.14.11.26
CAS: 69772-89-0

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