KEGG ORTHOLOGY: K18315

ORTHOLOGY: K18315

Entry

K18315                      KO

Symbol

cpmC, carC

Name

(5R)-carbapenem-3-carboxylate synthase [EC:1.14.20.3]

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

R10415

(3S,5S)-carbapenam-3-carboxylate,2-oxoglutarate:oxygen oxidoreductase (dehydrating)

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00332 Carbapenem biosynthesis
    K18315  cpmC, carC; (5R)-carbapenem-3-carboxylate synthase
09140 Cellular Processes
  09145 Cellular community - prokaryotes
   02024 Quorum sensing
    K18315  cpmC, carC; (5R)-carbapenem-3-carboxylate synthase
Enzymes [BR:ko01000]
1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.20  With 2-oxoglutarate as one donor, and the other dehydrogenated
    1.14.20.3  (5R)-carbapenem-3-carboxylate synthase
     K18315  cpmC, carC; (5R)-carbapenem-3-carboxylate synthase

Other DBs

COG:

COG2175

Genes

SERA:

SERQ:

PARI:

PPAV:

PCAC:

PACB:

DZE:	Dd1591_0211

DAQ:	DAQ1742_04176(cpmC)

PROD:

PCO85_15480

PAO:	Pat9b_5315

PLU:	plu0184(cpmC)

PLUM:

A4R40_00890

PTT:	VY86_09605

PRG:	RB151_027400(carC)

PRJ:	NCTC6933_00419

VSR:	Vspart_02937

VRU:	RND59_08410

BGP:	BGL_2c27600

BPLA:

bpln_2g27640

» 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: K18562

Entry

K18562                      KO

Symbol

thnQ, cmmQ

Name

2-oxoglutarate-dependent dioxygenase [EC:1.14.20.-]

Pathway

map00332

Carbapenem biosynthesis

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

Reaction

R10415

(3S,5S)-carbapenam-3-carboxylate,2-oxoglutarate:oxygen oxidoreductase (dehydrating)

R10735

OA-6129-A,2-oxoglutarate:oxygen oxidoreductase (8-hydroxylating)

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00332 Carbapenem biosynthesis
    K18562  thnQ, cmmQ; 2-oxoglutarate-dependent dioxygenase

Genes

DAG:	PSQ19_18825

DRP:	PSQ90_01635

GYJ:	AADW23_08005 AADW23_10430

STEL:

PAUU:

PSPN:

SFA:

STRP:

SMOB:

SFIY:

SCT:	SCAT_p0836(thnQ)

SCY:	SCATT_p08990

RHAL:

LQF10_09425

KSL:	OG809_24400

KRI:	OX958_24820

LEPT:

JVX88_35125

TOG:	HNI00_15945

TSIN:

OXH18_17685

PUO:	RZN69_18375

MTAR:

DF168_01250(ectD_7) DF168_01753 DF168_02179(ectD_10)

AMOB:

HG15A2_21170

BGOK:

Pr1d_47440(ptlH_2)

GFM:	Enr17x_01500(ptlH)

GAW:	V144x_19550

TPOL:

Mal48_27590 Mal48_34080(ptlH_2)

PVAR:

SH412_004081

RCG:	N7E81_07850

» show all

Reference

PMID:20017478

Authors

Bodner MJ, Phelan RM, Freeman MF, Li R, Townsend CA

Title

Non-heme iron oxygenases generate natural structural diversity in carbapenem antibiotics.

Journal

J Am Chem Soc 132:12-3 (2010)
DOI:10.1021/ja907320n

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_p0836]

Reference

PMID:24420617

Authors

Li R, Lloyd EP, Moshos KA, Townsend CA

Title

Identification and characterization of the carbapenem MM 4550 and its gene cluster in Streptomyces argenteolus ATCC 11009.

Journal

Chembiochem 15:320-31 (2014)
DOI:10.1002/cbic.201300319

LinkDB

ENZYME: 1.14.20.3

Entry

EC 1.14.20.3                Enzyme

Name

(5R)-carbapenem-3-carboxylate synthase;
carC (gene name)

Class

Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With 2-oxoglutarate as one donor, and the other dehydrogenated

Sysname

(3S,5S)-carbapenam-3-carboxylate,2-oxoglutarate:oxygen oxidoreductase (dehydrating)

Reaction(IUBMB)

(3S,5S)-carbapenam-3-carboxylate + 2-oxoglutarate + O2 = (5R)-carbapen-2-em-3-carboxylate + succinate + CO2 + H2O [RN:R10415]

Reaction(KEGG)

R10415

Substrate

(3S,5S)-carbapenam-3-carboxylate [CPD:C17367];
2-oxoglutarate [CPD:C00026];
O2 [CPD:C00007]

Product

(5R)-carbapen-2-em-3-carboxylate [CPD:C06669];
succinate [CPD:C00042];
CO2 [CPD:C00011];
H2O [CPD:C00001]

Comment

Requires Fe2+. The enzyme is involved in the biosynthesis of the carbapenem beta-lactam antibiotic (5R)-carbapen-2-em-3-carboxylate in the bacterium Pectobacterium carotovorum. It catalyses a stereoinversion at C-5 and introduces a double bond between C-2 and C-3.

History

EC 1.14.20.3 created 2013

Pathway

ec00332

Carbapenem biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K18315

(5R)-carbapenem-3-carboxylate synthase

Genes

SERA:

Ser39006_009930

SERQ:

CWC46_09925

PARI:

I2D83_01760

PPAV:

LOZ86_02770

PCAC:

OI450_17085

PACB:

M9782_00165

DZE:	Dd1591_0211

DAQ:	DAQ1742_04176(cpmC)

PROD:

PCO85_15480

PAO:	Pat9b_5315

PLU:	plu0184(cpmC)

PLUM:

A4R40_00890

PTT:	VY86_09605

PRG:	RB151_027400(carC)

PRJ:	NCTC6933_00419

VSR:	Vspart_02937

VRU:	RND59_08410

BGP:	BGL_2c27600

BPLA:

bpln_2g27640

» show all

Reference

1 [PMID:12611886]

Authors

Clifton IJ, Doan LX, Sleeman MC, Topf M, Suzuki H, Wilmouth RC, Schofield CJ

Title

Crystal structure of carbapenem synthase (CarC).

Journal

J Biol Chem 278:20843-50 (2003)
DOI:10.1074/jbc.M213054200

Reference

2 [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

Reference

3 [PMID:15174175]

Authors

Sleeman MC, Smith P, Kellam B, Chhabra SR, Bycroft BW, Schofield CJ

Title

Biosynthesis of carbapenem antibiotics: new carbapenam substrates for carbapenem synthase (CarC).

Journal

Chembiochem 5:879-82 (2004)
DOI:10.1002/cbic.200300908

Other DBs

ExplorEnz - The Enzyme Database:

1.14.20.3

IUBMB Enzyme Nomenclature:

1.14.20.3

ExPASy - ENZYME nomenclature database:

1.14.20.3

BRENDA, the Enzyme Database:

1.14.20.3

LinkDB

REACTION: R10415

Entry

R10415                      Reaction

Name

(3S,5S)-carbapenam-3-carboxylate,2-oxoglutarate:oxygen oxidoreductase (dehydrating)

Definition

(3S,5S)-Carbapenam-3-carboxylic acid + 2-Oxoglutarate + Oxygen <=> (5R)-Carbapen-2-em-3-carboxylate + Succinate + CO2 + H2O

Equation

C17367 + C00026 + C00007 <=> C06669 + C00042 + C00011 + C00001

Reaction class

RC03174

C06669_C17367

Enzyme

1.14.20.3 1.14.20.-

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]
1. Oxidoreductase reactions
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.20  With 2-oxoglutarate as one donor, and the other dehydrogenated
    1.14.20.3
     R10415  (3S,5S)-Carbapenam-3-carboxylic acid + 2-Oxoglutarate + Oxygen <=> (5R)-Carbapen-2-em-3-carboxylate + Succinate + CO2 + H2O
    1.14.20.-
     R10415  (3S,5S)-Carbapenam-3-carboxylic acid + 2-Oxoglutarate + Oxygen <=> (5R)-Carbapen-2-em-3-carboxylate + Succinate + CO2 + H2O

Orthology

K18315

(5R)-carbapenem-3-carboxylate synthase [EC:1.14.20.3]

K18562

2-oxoglutarate-dependent dioxygenase [EC:1.14.20.-]

Other DBs

RHEA:

36614

LinkDB

DBGET integrated database retrieval system