KEGG   ORTHOLOGY: K18315
Entry
K18315                      KO                                     
Symbol
cpmC, carC
Name
(5R)-carbapenem-3-carboxylate synthase [EC:1.14.20.3]
Pathway
map00332  Carbapenem biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
map02024  Quorum sensing
Module
M00675  Carbapenem-3-carboxylate biosynthesis, pyrroline-5-carboxylate + malonyl-CoA => carbapenem-3-carboxylate
Reaction
R10415  (3S,5S)-carbapenam-3-carboxylate,2-oxoglutarate:oxygen oxidoreductase (dehydrating)
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
COG: COG2175
Genes
SERA: Ser39006_009930
SERQ: CWC46_09925
PARI: I2D83_01760
PPAV: LOZ86_02770
PCAC: OI450_17085
PACB: M9782_00165
DZE: Dd1591_0211
DAQ: DAQ1742_04176(cpmC)
PROD: PCO85_15480
PAO: Pat9b_5315
PLU: plu0184(cpmC)
PLUM: A4R40_00890
PTT: VY86_09605
PRG: RB151_027400(carC)
PRJ: NCTC6933_00419
VSR: Vspart_02937
VRU: RND59_08410
BGP: BGL_2c27600
BPLA: bpln_2g27640
 » show all
Reference
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
LinkDB

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
PARI: I2D83_01760
PPAV: LOZ86_02770
PCAC: OI450_17085
PACB: M9782_00165
DZE: Dd1591_0211
DAQ: DAQ1742_04176(cpmC)
PROD: PCO85_15480
PAO: Pat9b_5315
PLU: plu0184(cpmC)
PLUM: A4R40_00890
PTT: VY86_09605
PRG: RB151_027400(carC)
PRJ: NCTC6933_00419
VSR: Vspart_02937
VRU: RND59_08410
BGP: BGL_2c27600
BPLA: bpln_2g27640
 » 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
LinkDB

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
C17367 + C00026 + C00007 <=> C06669 + C00042 + C00011 + C00001
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
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
    1.14.20.3
     R10415  (3S,5S)-Carbapenam-3-carboxylic acid + 2-Oxoglutarate + Oxygen <=> (5R)-Carbapen-2-em-3-carboxylate + Succinate + CO2 + H2O
    1.14.20.-
     R10415  (3S,5S)-Carbapenam-3-carboxylic acid + 2-Oxoglutarate + Oxygen <=> (5R)-Carbapen-2-em-3-carboxylate + Succinate + CO2 + H2O
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
LinkDB

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