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Entry
EC 6.3.3.4                  Enzyme                                 

Name
(carboxyethyl)arginine beta-lactam-synthase;
L-2-N-(2-carboxyethyl)arginine cyclo-ligase (AMP-forming)
Class
Ligases;
Forming carbon-nitrogen bonds;
Cyclo-ligases
BRITE hierarchy
Sysname
L-N2-(2-carboxyethyl)arginine cyclo-ligase (AMP-forming)
Reaction(IUBMB)
ATP + L-N2-(2-carboxyethyl)arginine = AMP + diphosphate + deoxyamidinoproclavaminate [RN:R05467]
Reaction(KEGG)
Substrate
ATP [CPD:C00002];
L-N2-(2-carboxyethyl)arginine [CPD:C06655]
Product
AMP [CPD:C00020];
diphosphate [CPD:C00013];
deoxyamidinoproclavaminate [CPD:C06656]
Comment
Forms part of the pathway for the biosythesis of the beta-lactamase inhibitor clavulanate in Streptomyces clavuligerus. It has been proposed [3] that L-N2-(2-carboxyethyl)arginine is first converted into an acyl-AMP by reaction with ATP and loss of diphosphate, and that the beta-lactam ring is then formed by the intramolecular attack of the beta-nitrogen on the activated carboxy group.
History
EC 6.3.3.4 created 2003
Pathway
ec00331  Clavulanic acid biosynthesis
ec01130  Biosynthesis of antibiotics
Orthology
K12674  (carboxyethyl)arginine beta-lactam-synthase
Genes
SFA: Sfla_0556
STRP: F750_6323
SCLF: BB341_07810
SFK: KY5_8017c
KAB: B7C62_18885
KAU: B6264_26750
SVI: Svir_33380
Taxonomy
Reference
1  [PMID:11472170]
  Authors
Zhou J, Kelly WL, Bachmann BO, Gunsior M, Townsend CA, Solomon EI.
  Title
Spectroscopic studies of substrate interactions with clavaminate synthase 2, a multifunctional alpha-KG-dependent non-heme iron enzyme: correlation with mechanisms and reactivities.
  Journal
J Am Chem Soc 123:7388-98 (2001)
DOI:10.1021/ja004025+
Reference
2  [PMID:12413541]
  Authors
Townsend CA.
  Title
New reactions in clavulanic acid biosynthesis.
  Journal
Curr Opin Chem Biol 6:583-9 (2002)
DOI:10.1016/S1367-5931(02)00392-7
Reference
3  [PMID:9689037]
  Authors
Bachmann BO, Li R, Townsend CA.
  Title
beta-Lactam synthetase: a new biosynthetic enzyme.
  Journal
Proc Natl Acad Sci U S A 95:9082-6 (1998)
DOI:10.1073/pnas.95.16.9082
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 6.3.3.4
IUBMB Enzyme Nomenclature: 6.3.3.4
ExPASy - ENZYME nomenclature database: 6.3.3.4
BRENDA, the Enzyme Database: 6.3.3.4

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