KEGG ORTHOLOGY: K12743

ORTHOLOGY: K12743

Entry

K12743                      KO

Symbol

PCBAB

Name

N-(5-amino-5-carboxypentanoyl)-L-cysteinyl-D-valine synthase [EC:6.3.2.26]

Pathway

map00311

Penicillin and cephalosporin biosynthesis

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

Module

M00672

Penicillin biosynthesis, aminoadipate + cycteine + valine => penicillin

M00673

Cephamycin C biosynthesis, aminoadipate + cycteine + valine => cephamycin C

Reaction

R04870

L-2-aminohexanedioate:L-cysteine:L-valine ligase (AMP-forming, valine-inverting)

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00311 Penicillin and cephalosporin biosynthesis
    K12743  PCBAB; N-(5-amino-5-carboxypentanoyl)-L-cysteinyl-D-valine synthase
09180 Brite Hierarchies
  09181 Protein families: metabolism
   01008 Polyketide biosynthesis proteins
    K12743  PCBAB; N-(5-amino-5-carboxypentanoyl)-L-cysteinyl-D-valine synthase
Enzymes [BR:ko01000]
6. Ligases
  6.3  Forming carbon-nitrogen bonds
   6.3.2  Acid-D-amino-acid ligases (peptide synthases)
    6.3.2.26  N-(5-amino-5-carboxypentanoyl)-L-cysteinyl-D-valine synthase
     K12743  PCBAB; N-(5-amino-5-carboxypentanoyl)-L-cysteinyl-D-valine synthase
Polyketide biosynthesis proteins [BR:ko01008]
Nonribosomal peptide synthetase (NRPS)
  Linear NRPS
   ACV synthetase
    K12743  PCBAB; N-(5-amino-5-carboxypentanoyl)-L-cysteinyl-D-valine synthase

Other DBs

GO:

0050564

Genes

BCOO:

119075341

PMEO:

129593796 129595266

PCHM:

VFPPC_08658

ANI:	ANIA_02621

AOR:	AO090038000543

AFV:	AFLA_009029

APUU:

APUU_12364S

ABE:

ARB_02226

TVE:

TRV_00553

XRY:	QN244_11740

SCLF:

BB341_07790

STIR:

DDW44_23095

SCT:	SCAT_5684(pcbAB)

SCY:	SCATT_56840

AAB:	A4R43_03220

AMYY:

YIM_39185(srfAA)

PSUU:

Psuf_059700

» show all

Reference

PMID:2061333

Authors

MacCabe AP, van Liempt H, Palissa H, Unkles SE, Riach MB, Pfeifer E, von Dohren H, Kinghorn JR

Title

Delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine synthetase from Aspergillus nidulans. Molecular characterization of the acvA gene encoding the first enzyme of the penicillin biosynthetic pathway.

Journal

J Biol Chem 266:12646-54 (1991)
DOI:10.1016/S0021-9258(18)98948-9

Sequence

[ani:ANIA_02621]

LinkDB

ENZYME: 6.3.2.26

Entry

EC 6.3.2.26                 Enzyme

Name

N-(5-amino-5-carboxypentanoyl)-L-cysteinyl-D-valine synthase;
L-delta-(alpha-aminoadipoyl)-L-cysteinyl-D-valine synthetase;
ACV synthetase;
L-alpha-aminoadipyl-cysteinyl-valine synthetase

Class

Ligases;
Forming carbon-nitrogen bonds;
Acid-D-amino-acid ligases (peptide synthases)

Sysname

L-2-aminohexanedioate:L-cysteine:L-valine ligase (AMP-forming, valine-inverting)

Reaction(IUBMB)

3 ATP + L-2-aminohexanedioate + L-cysteine + L-valine + H2O = 3 AMP + 3 diphosphate + N-[L-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine [RN:R04870]

Reaction(KEGG)

R04870

Substrate

ATP [CPD:C00002];
L-2-aminohexanedioate [CPD:C00956];
L-cysteine [CPD:C00097];
L-valine [CPD:C00183];
H2O [CPD:C00001]

Product

AMP [CPD:C00020];
diphosphate [CPD:C00013];
N-[L-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine [CPD:C05556]

Comment

Requires Mg2+. The enzyme contains 4'-phosphopantetheine, which may be involved in the mechanism of the reaction. Forms part of the penicillin biosynthesis pathway (for pathway, click here).

History

EC 6.3.2.26 created 2002

Pathway

ec00311

Penicillin and cephalosporin biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K12743

N-(5-amino-5-carboxypentanoyl)-L-cysteinyl-D-valine synthase

Genes

BCOO:

119075341

PMEO:

129593796 129595266

PCHM:

VFPPC_08658

ANI:	ANIA_02621

AOR:	AO090038000543

AFV:	AFLA_009029

APUU:

APUU_12364S

ABE:

ARB_02226

TVE:

TRV_00553

XRY:	QN244_11740

SCLF:

BB341_07790

STIR:

DDW44_23095

SCT:	SCAT_5684(pcbAB)

SCY:	SCATT_56840

AAB:	A4R43_03220

AMYY:

YIM_39185(srfAA)

PSUU:

Psuf_059700

» show all

Reference

1 [PMID:11851475]

Authors

Byford MF, Baldwin JE, Shiau CY, Schofield CJ.

Title

The Mechanism of ACV Synthetase.

Journal

Chem Rev 97:2631-2650 (1997)
DOI:10.1021/cr960018l

Reference

2 [PMID:9355751]

Authors

Theilgaard HB, Kristiansen KN, Henriksen CM, Nielsen J.

Title

Purification and characterization of delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine synthetase from Penicillium chrysogenum.

Journal

Biochem J 327 ( Pt 1):185-91 (1997)
DOI:10.1042/bj3270185

Other DBs

ExplorEnz - The Enzyme Database:

6.3.2.26

IUBMB Enzyme Nomenclature:

6.3.2.26

ExPASy - ENZYME nomenclature database:

6.3.2.26

BRENDA, the Enzyme Database:

6.3.2.26

CAS:	57219-73-5

LinkDB

REACTION: R04870

Entry

R04870                      Reaction

Name

L-2-aminohexanedioate:L-cysteine:L-valine ligase (AMP-forming, valine-inverting)

Definition

L-2-Aminoadipate + L-Valine + L-Cysteine + 3 ATP + H2O <=> delta-(L-2-Aminoadipyl)-L-cysteinyl-D-valine + 3 AMP + 3 Diphosphate

Equation

C00956 + C00183 + C00097 + 3 C00002 + C00001 <=> C05556 + 3 C00020 + 3 C00013

Comment

multi-step reaction

Reaction class

RC00090

C00956_C05556

RC01227

C00097_C05556

RC01228

C00183_C05556

Enzyme

6.3.2.26

Pathway

rn00311

Penicillin and cephalosporin biosynthesis

rn01100

Metabolic pathways

rn01110

Biosynthesis of secondary metabolites

Module

M00672

Penicillin biosynthesis, aminoadipate + cycteine + valine => penicillin

M00673

Cephamycin C biosynthesis, aminoadipate + cycteine + valine => cephamycin C

Brite

Enzymatic reactions [BR:br08201]
6. Ligase reactions
  6.3  Forming carbon-nitrogen bonds
   6.3.2  Acid-D-amino-acid ligases (peptide synthases)
    6.3.2.26
     R04870  L-2-Aminoadipate + L-Valine + L-Cysteine + 3 ATP + H2O <=> delta-(L-2-Aminoadipyl)-L-cysteinyl-D-valine + 3 AMP + 3 Diphosphate

Orthology

K12743

N-(5-amino-5-carboxypentanoyl)-L-cysteinyl-D-valine synthase [EC:6.3.2.26]

Other DBs

RHEA:

23199

LinkDB

DBGET integrated database retrieval system