KEGG   ENZYME: 2.3.1.226
Entry
EC 2.3.1.226                Enzyme                                 
Name
carboxymethylproline synthase;
CarB (ambiguous)
Class
Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups
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)
R10485
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
ec00332  Carbapenem biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K18317  carboxymethylproline synthase
K18583  carboxymethylproline synthase
Genes
SERASer39006_009925
SERQCWC46_09920
PARII2D83_01755
PPAVLOZ86_02765
DZEDd1591_0212
DAQDAQ1742_04175(cpmB)
PAOPat9b_5316
PLUplu0183(cpmB)
PLUMA4R40_00885
PTTVY86_09610
PRGRB151_027390(echA8)
VSRVspart_02936(echA8)
BGPBGL_2c27610
BPLAbpln_2g27650
BVZBRAD3257_7533
PFTJBW_01239
SCTSCAT_p0824(thnE)
SCYSCATT_p09110
SFASfla_0164
STRPF750_6857
 » show all
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 279:6730-6 (2004)
DOI:10.1074/jbc.M311824200
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 43:15936-45 (2004)
DOI:10.1021/bi0483662
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) 1155-7 (2005)
DOI:10.1039/b416423g
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 280:34956-65 (2005)
DOI:10.1074/jbc.M507196200
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 47:9322-5 (2008)
DOI:10.1002/anie.200803906
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 3:365-71 (2011)
DOI:10.1038/nchem.1011
Other DBs
ExplorEnz - The Enzyme Database: 2.3.1.226
IUBMB Enzyme Nomenclature: 2.3.1.226
ExPASy - ENZYME nomenclature database: 2.3.1.226
BRENDA, the Enzyme Database: 2.3.1.226

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