KEGG ENZYME: 2.3.1.226

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

PROD:

PCO85_15485

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)

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

PFT:

JBW_01239

SFA:

Sfla_0164

STRP:

F750_6857

SFIY:

F0344_10135

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

DBGET integrated database retrieval system