KEGG   ORTHOLOGY: K12744
Entry
K12744                      KO                                     
Symbol
cefE
Name
deacetoxycephalosporin-C synthase [EC:1.14.20.1]
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
R05301  penicillin-N,2-oxoglutarate:oxygen oxidoreductase (ring-expanding)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00311 Penicillin and cephalosporin biosynthesis
    K12744  cefE; deacetoxycephalosporin-C synthase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   01008 Polyketide biosynthesis proteins
    K12744  cefE; deacetoxycephalosporin-C synthase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.20  With 2-oxoglutarate as one donor, and the other dehydrogenated
    1.14.20.1  deacetoxycephalosporin-C synthase
     K12744  cefE; deacetoxycephalosporin-C synthase
Polyketide biosynthesis proteins [BR:ko01008]
 Nonribosomal peptide tailoring proteins
  Others
   K12744  cefE; deacetoxycephalosporin-C synthase
Other DBs
GO: 0050599
Genes
XRY: QN244_11750
SCLF: BB341_07740
SCT: SCAT_5687(cefE)
SCY: SCATT_56870
AAB: A4R43_03205
AMYY: YIM_39200(cefE2)
Reference
PMID:2644235
  Authors
Kovacevic S, Weigel BJ, Tobin MB, Ingolia TD, Miller JR
  Title
Cloning, characterization, and expression in Escherichia coli of the Streptomyces clavuligerus gene encoding deacetoxycephalosporin C synthetase.
  Journal
J Bacteriol 171:754-60 (1989)
DOI:10.1128/JB.171.2.754-760.1989
  Sequence
[sclf:BB341_07740]
LinkDB

KEGG   ENZYME: 1.14.20.1
Entry
EC 1.14.20.1                Enzyme                                 
Name
deacetoxycephalosporin-C synthase;
DAOCS;
penicillin N expandase;
DAOC synthase
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With 2-oxoglutarate as one donor, and the other dehydrogenated
Sysname
penicillin-N,2-oxoglutarate:oxygen oxidoreductase (ring-expanding)
Reaction(IUBMB)
penicillin N + 2-oxoglutarate + O2 = deacetoxycephalosporin C + succinate + CO2 + H2O [RN:R05301]
Reaction(KEGG)
R05301
Substrate
penicillin N [CPD:C06564];
2-oxoglutarate [CPD:C00026];
O2 [CPD:C00007]
Product
deacetoxycephalosporin C [CPD:C06565];
succinate [CPD:C00042];
CO2 [CPD:C00011];
H2O [CPD:C00001]
Comment
Forms part of the penicillin biosynthesis pathway (for pathway, click here).
History
EC 1.14.20.1 created 2002
Pathway
ec00311  Penicillin and cephalosporin biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K12744  deacetoxycephalosporin-C synthase
Genes
XRY: QN244_11750
SCLF: BB341_07740
SCT: SCAT_5687(cefE)
SCY: SCATT_56870
AAB: A4R43_03205
AMYY: YIM_39200(cefE2)
Reference
1  [PMID:1354366]
  Authors
Cantwell C, Beckmann R, Whiteman P, Queener SW, Abraham EP.
  Title
Isolation of deacetoxycephalosporin C from fermentation broths of Penicillium chrysogenum transformants: construction of a new fungal biosynthetic pathway.
  Journal
Proc R Soc Lond B Biol Sci 248:283-9 (1992)
DOI:10.1098/rspb.1992.0073
Reference
2  [PMID:11352583]
  Authors
Lee HJ, Lloyd MD, Harlos K, Clifton IJ, Baldwin JE, Schofield CJ.
  Title
Kinetic and crystallographic studies on deacetoxycephalosporin C synthase (DAOCS).
  Journal
J Mol Biol 308:937-48 (2001)
DOI:10.1006/jmbi.2001.4649
  Sequence
[sclf:BB341_07740]
Reference
3
  Authors
Yeh WK, Ghag SK, Queener SW.
  Title
Enzymes for epimerization of isopenicillin N, ring expansion of penicillin N, and 3'-hydroxylation of deacetoxycephalosporin C. Function, evolution, refolding, and enzyme engineering.
  Journal
Ann NY Acad Sci 672:396-408 (1992)
Reference
4  [PMID:9723623]
  Authors
Valegard K, van Scheltinga AC, Lloyd MD, Hara T, Ramaswamy S, Perrakis A, Thompson A, Lee HJ, Baldwin JE, Schofield CJ, Hajdu J, Andersson I.
  Title
Structure of a cephalosporin synthase.
  Journal
Nature 394:805-9 (1998)
DOI:10.1038/29575
  Sequence
[sclf:BB341_07740]
Reference
5  [PMID:2656705]
  Authors
Dotzlaf JE, Yeh WK.
  Title
Purification and properties of deacetoxycephalosporin C synthase from recombinant Escherichia coli and its comparison with the native enzyme purified from Streptomyces clavuligerus.
  Journal
J Biol Chem 264:10219-27 (1989)
Other DBs
ExplorEnz - The Enzyme Database: 1.14.20.1
IUBMB Enzyme Nomenclature: 1.14.20.1
ExPASy - ENZYME nomenclature database: 1.14.20.1
BRENDA, the Enzyme Database: 1.14.20.1
CAS: 85746-10-7
LinkDB

KEGG   REACTION: R05301
Entry
R05301                      Reaction                               
Name
penicillin-N,2-oxoglutarate:oxygen oxidoreductase (ring-expanding)
Definition
Penicillin N + 2-Oxoglutarate + Oxygen <=> Deacetoxycephalosporin C + Succinate + CO2 + H2O
Equation
C06564 + C00026 + C00007 <=> C06565 + C00042 + C00011 + C00001
Reaction class
RC01322  C06564_C06565
Enzyme
1.14.20.1
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
   1.14.20  With 2-oxoglutarate as one donor, and the other dehydrogenated
    1.14.20.1
     R05301  Penicillin N + 2-Oxoglutarate + Oxygen <=> Deacetoxycephalosporin C + Succinate + CO2 + H2O
Orthology
K12744  deacetoxycephalosporin-C synthase [EC:1.14.20.1]
Other DBs
RHEA: 20751
LinkDB

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