KEGG   ORTHOLOGY: K18315
Entry
K18315                      KO                                     

Name
cpmC, carC
Definition
(5R)-carbapenem-3-carboxylate synthase [EC:1.14.20.3]
Pathway
ko00332  Carbapenem biosynthesis
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
ko02024  Quorum sensing
Module
M00675  Carbapenem-3-carboxylate biosynthesis, pyrroline-5-carboxylate + malonyl-CoA => carbapenem-3-carboxylate
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00332 Carbapenem biosynthesis
    K18315  cpmC, carC; (5R)-carbapenem-3-carboxylate synthase
 09140 Cellular Processes
  09145 Cellular community - prokaryotes
   02024 Quorum sensing
    K18315  cpmC, carC; (5R)-carbapenem-3-carboxylate 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
    1.14.20.3  (5R)-carbapenem-3-carboxylate synthase
     K18315  cpmC, carC; (5R)-carbapenem-3-carboxylate synthase
Other DBs
RN: R10415
COG: COG2175
Genes
SERA: Ser39006_009930
SERQ: CWC46_09925
DZE: Dd1591_0211
DAQ: DAQ1742_04176(cpmC)
PAO: Pat9b_5315
PLU: plu0184(cpmC)
PLUM: A4R40_00890
PTT: VY86_09605
PRG: RB151_027400(carC)
PRJ: NCTC6933_00419
 » show all
Reference
  Authors
Stapon A, Li R, Townsend CA
  Title
Carbapenem biosynthesis: confirmation of stereochemical assignments and the role of CarC in the ring stereoinversion process from L-proline.
  Journal
J Am Chem Soc 125:8486-93 (2003)
DOI:10.1021/ja034248a

KEGG   ORTHOLOGY: K18562
Entry
K18562                      KO                                     

Name
thnQ, cmmQ
Definition
2-oxoglutarate-dependent dioxygenase [EC:1.14.20.-]
Pathway
ko00332  Carbapenem biosynthesis
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00332 Carbapenem biosynthesis
    K18562  thnQ, cmmQ; 2-oxoglutarate-dependent dioxygenase
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.-  
     K18562  thnQ, cmmQ; 2-oxoglutarate-dependent dioxygenase
Other DBs
RN: R10415 R10735
Genes
SCT: SCAT_p0836(thnQ)
SCY: SCATT_p08990
SFA: Sfla_0152
STRP: F750_6869
Reference
  Authors
Bodner MJ, Phelan RM, Freeman MF, Li R, Townsend CA
  Title
Non-heme iron oxygenases generate natural structural diversity in carbapenem antibiotics.
  Journal
J Am Chem Soc 132:12-3 (2010)
DOI:10.1021/ja907320n
Reference
  Authors
Rodriguez M, Nunez LE, Brana AF, Mendez C, Salas JA, Blanco G
  Title
Mutational analysis of the thienamycin biosynthetic gene cluster from Streptomyces cattleya.
  Journal
Antimicrob Agents Chemother 55:1638-49 (2011)
DOI:10.1128/AAC.01366-10
  Sequence
Reference
  Authors
Li R, Lloyd EP, Moshos KA, Townsend CA
  Title
Identification and characterization of the carbapenem MM 4550 and its gene cluster in Streptomyces argenteolus ATCC 11009.
  Journal
Chembiochem 15:320-31 (2014)
DOI:10.1002/cbic.201300319

KEGG   ENZYME: 1.14.20.3
Entry
EC 1.14.20.3                Enzyme                                 

Name
(5R)-carbapenem-3-carboxylate synthase;
carC (gene name)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With 2-oxoglutarate as one donor, and the other dehydrogenated
Sysname
(3S,5S)-carbapenam-3-carboxylate,2-oxoglutarate:oxygen oxidoreductase (dehydrating)
Reaction(IUBMB)
(3S,5S)-carbapenam-3-carboxylate + 2-oxoglutarate + O2 = (5R)-carbapen-2-em-3-carboxylate + succinate + CO2 + H2O [RN:R10415]
Reaction(KEGG)
R10415
Substrate
(3S,5S)-carbapenam-3-carboxylate [CPD:C17367];
2-oxoglutarate [CPD:C00026];
O2 [CPD:C00007]
Product
(5R)-carbapen-2-em-3-carboxylate [CPD:C06669];
succinate [CPD:C00042];
CO2 [CPD:C00011];
H2O [CPD:C00001]
Comment
Requires Fe2+. The enzyme is involved in the biosynthesis of the carbapenem beta-lactam antibiotic (5R)-carbapen-2-em-3-carboxylate in the bacterium Pectobacterium carotovorum. It catalyses a stereoinversion at C-5 and introduces a double bond between C-2 and C-3.
History
EC 1.14.20.3 created 2013
Pathway
ec00332  Carbapenem biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K18315  (5R)-carbapenem-3-carboxylate synthase
Genes
SERA: Ser39006_009930
SERQ: CWC46_09925
DZE: Dd1591_0211
DAQ: DAQ1742_04176(cpmC)
PAO: Pat9b_5315
PLU: plu0184(cpmC)
PLUM: A4R40_00890
PTT: VY86_09605
PRG: RB151_027400(carC)
PRJ: NCTC6933_00419
 » show all
Reference
1  [PMID:12611886]
  Authors
Clifton IJ, Doan LX, Sleeman MC, Topf M, Suzuki H, Wilmouth RC, Schofield CJ
  Title
Crystal structure of carbapenem synthase (CarC).
  Journal
J Biol Chem 278:20843-50 (2003)
DOI:10.1074/jbc.M213054200
Reference
2  [PMID:12848554]
  Authors
Stapon A, Li R, Townsend CA
  Title
Carbapenem biosynthesis: confirmation of stereochemical assignments and the role  of CarC in the ring stereoinversion process from L-proline.
  Journal
J Am Chem Soc 125:8486-93 (2003)
DOI:10.1021/ja034248a
Reference
3  [PMID:15174175]
  Authors
Sleeman MC, Smith P, Kellam B, Chhabra SR, Bycroft BW, Schofield CJ
  Title
Biosynthesis of carbapenem antibiotics: new carbapenam substrates for carbapenem  synthase (CarC).
  Journal
Chembiochem 5:879-82 (2004)
DOI:10.1002/cbic.200300908
Other DBs
ExplorEnz - The Enzyme Database: 1.14.20.3
IUBMB Enzyme Nomenclature: 1.14.20.3
ExPASy - ENZYME nomenclature database: 1.14.20.3
BRENDA, the Enzyme Database: 1.14.20.3

KEGG   REACTION: R10415
Entry
R10415                      Reaction                               

Name
(3S,5S)-carbapenam-3-carboxylate,2-oxoglutarate:oxygen oxidoreductase (dehydrating)
Definition
(3S,5S)-Carbapenam-3-carboxylic acid + 2-Oxoglutarate + Oxygen <=> (5R)-Carbapen-2-em-3-carboxylate + Succinate + CO2 + H2O
Equation
Reaction class
RC03174  C06669_C17367
Enzyme
1.14.20.3       1.14.20.-
Pathway
rn00332  Carbapenem biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00675  Carbapenem-3-carboxylate biosynthesis, pyrroline-5-carboxylate + malonyl-CoA => carbapenem-3-carboxylate
Orthology
K18315  (5R)-carbapenem-3-carboxylate synthase [EC:1.14.20.3]
K18562  2-oxoglutarate-dependent dioxygenase [EC:1.14.20.-]
Other DBs
RHEA: 36614

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