KEGG   ORTHOLOGY: K12745
Entry
K12745                      KO                                     
Symbol
cefF
Name
deacetoxycephalosporin-C hydroxylase [EC:1.14.11.26]
Pathway
map00311  Penicillin and cephalosporin biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00673  Cephamycin C biosynthesis, aminoadipate + cycteine + valine => cephamycin C
Reaction
R05229  
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00311 Penicillin and cephalosporin biosynthesis
    K12745  cefF; deacetoxycephalosporin-C hydroxylase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   01008 Polyketide biosynthesis proteins
    K12745  cefF; deacetoxycephalosporin-C hydroxylase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.11  With 2-oxoglutarate as one donor, and incorporation of one atom of oxygen into each donor
    1.14.11.26  deacetoxycephalosporin-C hydroxylase
     K12745  cefF; deacetoxycephalosporin-C hydroxylase
Polyketide biosynthesis proteins [BR:ko01008]
 Nonribosomal peptide tailoring proteins
  Others
   K12745  cefF; deacetoxycephalosporin-C hydroxylase
Other DBs
GO: 0045442
Genes
XRY: QN244_11755
SCLF: BB341_07760
SCT: SCAT_5681(cefF)
SCY: SCATT_56810
AAB: A4R43_03240
AMYY: YIM_39165(cefF)
PSUU: Psuf_059670
AG: AAA26716(cefF) CAA79803(cefF)
Reference
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
[ag:AAA26716]
Reference
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
[ag:CAA79803]
LinkDB

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
XRY: QN244_11755
SCLF: BB341_07760
SCT: SCAT_5681(cefF)
SCY: SCATT_56810
AAB: A4R43_03240
AMYY: YIM_39165(cefF)
PSUU: Psuf_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
[ag:AAA26716]
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
[ag:CAA79803]
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
LinkDB

KEGG   REACTION: R05229
Entry
R05229                      Reaction                               
Definition
Deacetylcephalosporin C + Succinate + CO2 <=> Deacetoxycephalosporin C + 2-Oxoglutarate + Oxygen
Equation
C03112 + C00042 + C00011 <=> C06565 + C00026 + C00007
Reaction class
RC00724  C03112_C06565
Enzyme
1.14.11.26
Pathway
rn00311  Penicillin and cephalosporin biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00673  Cephamycin C biosynthesis, aminoadipate + cycteine + valine => cephamycin C
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.11  With 2-oxoglutarate as one donor, and incorporation of one atom of oxygen into each donor
    1.14.11.26
     R05229  Deacetylcephalosporin C + Succinate + CO2 <=> Deacetoxycephalosporin C + 2-Oxoglutarate + Oxygen
Orthology
K12745  deacetoxycephalosporin-C hydroxylase [EC:1.14.11.26]
Other DBs
RHEA: 16808
LinkDB

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