KEGG ORTHOLOGY: K18317

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

Reaction

R10485

malonyl-CoA:(S)-1-pyrroline-5-carboxylate malonyltransferase (cyclizing)

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

COG:

COG1024

Genes

SERA:

SERQ:

PARI:

PPAV:

PCAC:

PACB:

DZE:	Dd1591_0212

DAQ:	DAQ1742_04175(cpmB)

PROD:

PCO85_15485

PAO:	Pat9b_5316

PLU:	plu0183(cpmB)

PLUM:

A4R40_00885

PTT:	VY86_09610

PRG:	RB151_027390(echA8)

VSR:	Vspart_02936(echA8)

VRU:	RND59_08415

BGP:	BGL_2c27610

BPLA:

bpln_2g27650

BVZ:	BRAD3257_7533

PFT:

JBW_01239

» 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

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

Reaction

R10485

malonyl-CoA:(S)-1-pyrroline-5-carboxylate malonyltransferase (cyclizing)

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

COG:

COG1024

Genes

BAUT:

QA635_32915 QA635_32930

BBRA:

QA636_34575

BRAY:

ML401_37740 ML401_37745

SFA:

STRP:

SFIY:

SCAJ:

SCT:	SCAT_p0824(thnE)

SCY:	SCATT_p09110

MENO:

Jiend_48450

Reference

PMID:21263049

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

[sct:SCAT_p0824]

Reference

PMID:19090510

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

PMID:21913298

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

LinkDB

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

SERA:

Ser39006_009925

SERQ:

CWC46_09920

PARI:

I2D83_01755

PPAV:

LOZ86_02765

PCAC:

OI450_17090

PACB:

M9782_00170

DZE:	Dd1591_0212

DAQ:	DAQ1742_04175(cpmB)

PROD:

PCO85_15485

PAO:	Pat9b_5316

PLU:	plu0183(cpmB)

PLUM:

A4R40_00885

PTT:	VY86_09610

PRG:	RB151_027390(echA8)

VSR:	Vspart_02936(echA8)

VRU:	RND59_08415

BGP:	BGL_2c27610

BPLA:

bpln_2g27650

BVZ:	BRAD3257_7533

BAUT:

QA635_32915 QA635_32930

BBRA:

QA636_34575

BRAY:

ML401_37740 ML401_37745

PFT:

JBW_01239

SFA:

Sfla_0164

STRP:

F750_6857

SFIY:

F0344_10135

SCAJ:

O1G22_15275

SCT:	SCAT_p0824(thnE)

SCY:	SCATT_p09110

MENO:

Jiend_48450

» 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

LinkDB

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

C00083 + C03912 + C00001 <=> C00010 + C17366 + C00011

Reaction class

RC00004

C00010_C00083

RC03182

C03912_C17366

Enzyme

2.3.1.226

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]
2. Transferase reactions
  2.3  Acyltransferases
   2.3.1  Transferring groups other than aminoacyl groups
    2.3.1.226
     R10485  Malonyl-CoA + (S)-1-Pyrroline-5-carboxylate + H2O <=> CoA + (2S,5S)-trans-Carboxymethylproline + CO2

Orthology

K18317

carboxymethylproline synthase [EC:2.3.1.226]

K18583

carboxymethylproline synthase [EC:2.3.1.226]

Other DBs

RHEA:

36666

LinkDB

DBGET integrated database retrieval system