KEGG   ORTHOLOGY: K12673
Entry
K12673                      KO                                     

Name
ceaS
Definition
N2-(2-carboxyethyl)arginine synthase [EC:2.5.1.66]
Pathway
ko00331  Clavulanic acid biosynthesis
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
Module
M00674  Clavaminate biosynthesis, arginine + glyceraldehyde-3P => clavaminate
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00331 Clavulanic acid biosynthesis
    K12673  ceaS; N2-(2-carboxyethyl)arginine synthase
Enzymes [BR:ko01000]
 2. Transferases
  2.5  Transferring alkyl or aryl groups, other than methyl groups
   2.5.1  Transferring alkyl or aryl groups, other than methyl groups (only sub-subclass identified to date)
    2.5.1.66  N2-(2-carboxyethyl)arginine synthase
     K12673  ceaS; N2-(2-carboxyethyl)arginine synthase
Other DBs
RN: R05465
GO: 0033848
Genes
SFA: Sfla_0555
STRP: F750_6324
SCLF: BB341_07805
SFK: KY5_8018c
KAB: B7C62_18880
KAU: B6264_26755
SVI: Svir_33370
Reference
PMID:14982786 (S.viridis)
  Authors
Tahlan K, Park HU, Wong A, Beatty PH, Jensen SE
  Title
Two sets of paralogous genes encode the enzymes involved in the early stages of clavulanic acid and clavam metabolite biosynthesis in Streptomyces clavuligerus.
  Journal
Antimicrob Agents Chemother 48:930-9 (2004)
DOI:10.1128/AAC.48.3.930-939.2004

KEGG   ENZYME: 2.5.1.66
Entry
EC 2.5.1.66                 Enzyme                                 

Name
N2-(2-carboxyethyl)arginine synthase;
CEAS;
N2-(2-carboxyethyl)arginine synthetase;
CEA synthetase;
glyceraldehyde-3-phosphate:L-arginine 2-N-(2-hydroxy-3-oxopropyl) transferase (2-carboxyethyl-forming)
Class
Transferases;
Transferring alkyl or aryl groups, other than methyl groups;
Transferring alkyl or aryl groups, other than methyl groups (only sub-subclass identified to date)
Sysname
glyceraldehyde-3-phosphate:L-arginine N2-(2-hydroxy-3-oxopropyl) transferase (2-carboxyethyl-forming)
Reaction(IUBMB)
D-glyceraldehyde 3-phosphate + L-arginine = N2-(2-carboxyethyl)-L-arginine + phosphate [RN:R05465]
Reaction(KEGG)
R05465
Substrate
D-glyceraldehyde 3-phosphate [CPD:C00118];
L-arginine [CPD:C00062]
Product
N2-(2-carboxyethyl)-L-arginine [CPD:C06655];
phosphate [CPD:C00009]
Comment
The enzyme requires thiamine diphosphate and catalyses the first step in the clavulanic-acid-biosynthesis pathway. The 2-hydroxy-3-oxo group transferred from glyceraldehyde 3-phosphate is isomerized during transfer to form the 2-carboxyethyl group.
History
EC 2.5.1.66 created 2004
Pathway
ec00331  Clavulanic acid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K12673  N2-(2-carboxyethyl)arginine synthase
Genes
SFA: Sfla_0555
STRP: F750_6324
SCLF: BB341_07805
SFK: KY5_8018c
KAB: B7C62_18880
KAU: B6264_26755
SVI: Svir_33370
Reference
1  [PMID:14623876]
  Authors
Caines ME, Elkins JM, Hewitson KS, Schofield CJ.
  Title
Crystal structure and mechanistic implications of N2-(2-carboxyethyl)arginine synthase, the first enzyme in the clavulanic acid biosynthesis pathway.
  Journal
J Biol Chem 279:5685-92 (2004)
DOI:10.1074/jbc.M310803200
  Sequence
Reference
2
  Authors
Khaleeli, N., Li, R. and Townsend, C.A.
  Title
Origin of the beta-lactam carbons in clavulanic acid from an unusual thiamine pyrophosphate-mediated reaction.
  Journal
J Am Chem Soc 121:9223-9224 (1999)
Other DBs
ExplorEnz - The Enzyme Database: 2.5.1.66
IUBMB Enzyme Nomenclature: 2.5.1.66
ExPASy - ENZYME nomenclature database: 2.5.1.66
BRENDA, the Enzyme Database: 2.5.1.66
CAS: 250207-48-8

KEGG   REACTION: R05465
Entry
R05465                      Reaction                               

Definition
D-Glyceraldehyde 3-phosphate + L-Arginine <=> L-N2-(2-Carboxyethyl)arginine + Orthophosphate
Equation
Reaction class
RC00215  C00062_C06655
Enzyme
Pathway
rn00331  Clavulanic acid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00674  Clavaminate biosynthesis, arginine + glyceraldehyde-3P => clavaminate
Orthology
K12673  N2-(2-carboxyethyl)arginine synthase [EC:2.5.1.66]
Other DBs
RHEA: 10559

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