KEGG   ORTHOLOGY: K18317
Entry
K18317                      KO                                     
Symbol
cpmB, carB
Name
carboxymethylproline synthase [EC:2.3.1.226]
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
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00332 Carbapenem biosynthesis
    K18317  cpmB, carB; carboxymethylproline synthase
 09140 Cellular Processes
  09145 Cellular community - prokaryotes
   02024 Quorum sensing
    K18317  cpmB, carB; carboxymethylproline synthase
Enzymes [BR:ko01000]
 2. Transferases
  2.3  Acyltransferases
   2.3.1  Transferring groups other than aminoacyl groups
    2.3.1.226  carboxymethylproline synthase
     K18317  cpmB, carB; carboxymethylproline synthase
Other DBs
RN: R10485
COG: COG1024
Genes
SERA: Ser39006_009925
SERQ: CWC46_09920
PARI: I2D83_01755
PPAV: LOZ86_02765
DZE: Dd1591_0212
DAQ: DAQ1742_04175(cpmB)
PAO: Pat9b_5316
PLU: plu0183(cpmB)
PLUM: A4R40_00885
PTT: VY86_09610
PRG: RB151_027390(echA8)
VSR: Vspart_02936(echA8)
PFT: JBW_01239
 » 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: K18583
Entry
K18583                      KO                                     
Symbol
thnE
Name
carboxymethylproline synthase [EC:2.3.1.226]
Pathway
map00332  Carbapenem biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00332 Carbapenem biosynthesis
    K18583  thnE; carboxymethylproline synthase
Enzymes [BR:ko01000]
 2. Transferases
  2.3  Acyltransferases
   2.3.1  Transferring groups other than aminoacyl groups
    2.3.1.226  carboxymethylproline synthase
     K18583  thnE; carboxymethylproline synthase
Other DBs
RN: R10485
COG: COG1024
Genes
SCT: SCAT_p0824(thnE)
SCY: SCATT_p09110
SFA: Sfla_0164
STRP: F750_6857
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
Hamed RB, Batchelar ET, Mecinovic J, Claridge TD, Schofield CJ
  Title
Evidence that thienamycin biosynthesis proceeds via C-5 epimerization: ThnE catalyzes the formation of (2S,5S)-trans-carboxymethylproline.
  Journal
Chembiochem 10:246-50 (2009)
DOI:10.1002/cbic.200800652
Reference
  Authors
Bodner MJ, Li R, Phelan RM, Freeman MF, Moshos KA, Lloyd EP, Townsend CA
  Title
Definition of the common and divergent steps in carbapenem beta-lactam antibiotic biosynthesis.
  Journal
Chembiochem 12:2159-65 (2011)
DOI:10.1002/cbic.201100366

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

KEGG   REACTION: R10485
Entry
R10485                      Reaction                               
Name
malonyl-CoA:(S)-1-pyrroline-5-carboxylate malonyltransferase (cyclizing)
Definition
Malonyl-CoA + (S)-1-Pyrroline-5-carboxylate + H2O <=> CoA + (2S,5S)-trans-Carboxymethylproline + CO2
Equation
Reaction class
RC00004  C00010_C00083
RC03182  C03912_C17366
Enzyme
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
K18317  carboxymethylproline synthase [EC:2.3.1.226]
K18583  carboxymethylproline synthase [EC:2.3.1.226]
Other DBs
RHEA: 36666

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