KEGG   ENZYME: 2.3.1.226Help
Entry
EC 2.3.1.226                Enzyme                                 

Name
carboxymethylproline synthase;
CarB (ambiguous)
Class
Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups
BRITE hierarchy
Sysname
malonyl-CoA:(S)-1-pyrroline-5-carboxylate malonyltransferase (cyclizing)
Reaction(IUBMB)
malonyl-CoA + (S)-1-pyrroline-5-carboxylate + H2O = CoA + (2S,5S)-5-carboxymethylproline + CO2 [RN:R10485]
Reaction(KEGG)
Substrate
malonyl-CoA [CPD:C00083];
(S)-1-pyrroline-5-carboxylate [CPD:C03912];
H2O [CPD:C00001]
Product
CoA [CPD:C00010];
(2S,5S)-5-carboxymethylproline [CPD:C17366];
CO2 [CPD:C00011]
Comment
The enzyme is involved in the biosynthesis of the carbapenem beta-lactam antibiotic (5R)-carbapen-2-em-3-carboxylate in the bacterium Pectobacterium carotovorum.
History
EC 2.3.1.226 created 2013
Pathway
Carbapenem biosynthesis
Biosynthesis of antibiotics
Orthology
K18317  
carboxymethylproline synthase
K18583  
carboxymethylproline synthase
Genes
DZE: 
PAO: 
PLU: 
plu0183(cpmB)
PTT: 
PRG: 
SCT: 
SCY: 
SFA: 
STRP: 
Taxonomy
Reference
1  [PMID:14625287]
  Authors
Sleeman MC, Schofield CJ
  Title
Carboxymethylproline synthase (CarB), an unusual carbon-carbon bond-forming enzyme of the crotonase superfamily involved in carbapenem biosynthesis.
  Journal
J. Biol. Chem. 279 (2004) 6730-6.
Reference
2  [PMID:15595850]
  Authors
Gerratana B, Arnett SO, Stapon A, Townsend CA
  Title
Carboxymethylproline synthase from Pectobacterium carotorova: a multifaceted member of the crotonase superfamily.
  Journal
Biochemistry. 43 (2004) 15936-45.
Reference
3  [PMID:15726176]
  Authors
Sorensen JL, Sleeman MC, Schofield CJ
  Title
Synthesis of deuterium labelled L- and D-glutamate semialdehydes and their evaluation as substrates for carboxymethylproline synthase (CarB)--implications for carbapenem biosynthesis.
  Journal
Chem. Commun. (Camb).  (2005) 1155-7.
Reference
4  [PMID:16096274]
  Authors
Sleeman MC, Sorensen JL, Batchelar ET, McDonough MA, Schofield CJ
  Title
Structural and mechanistic studies on carboxymethylproline synthase (CarB), a unique member of the crotonase superfamily catalyzing the first step in carbapenem biosynthesis.
  Journal
J. Biol. Chem. 280 (2005) 34956-65.
Reference
5  [PMID:18972478]
  Authors
Batchelar ET, Hamed RB, Ducho C, Claridge TD, Edelmann MJ, Kessler B, Schofield CJ
  Title
Thioester hydrolysis and C-C bond formation by carboxymethylproline synthase from the crotonase superfamily.
  Journal
Angew. Chem. Int. Ed. Engl. 47 (2008) 9322-5.
Reference
6  [PMID:21505494]
  Authors
Hamed RB, Gomez-Castellanos JR, Thalhammer A, Harding D, Ducho C, Claridge TD, Schofield CJ
  Title
Stereoselective C-C bond formation catalysed by engineered carboxymethylproline synthases.
  Journal
Nat. Chem. 3 (2011) 365-71.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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