KEGG   ORTHOLOGY: K12673
Entry
K12673                      KO                                     
Symbol
ceaS
Name
N2-(2-carboxyethyl)arginine synthase [EC:2.5.1.66]
Pathway
map00331  Clavulanic acid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00674  Clavaminate biosynthesis, arginine + glyceraldehyde-3P => clavaminate
Reaction
R05465  
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
GO: 0033848
Genes
SYM: K6K13_21960
AAYD: B379_05105
SFA: Sfla_0555
STRP: F750_6324
SCLF: BB341_07805 BB341_29465
SGM: GCM10017557_20580
SFK: KY5_8018c
SKA: CP970_43095
SVR: CP971_33685
SSPB: CP982_00540
 » show all
Reference
  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
Reference
  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
  Sequence
LinkDB

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
SYMK6K13_21960
AAYDB379_05105
SFASfla_0555
STRPF750_6324
SCLFBB341_07805 BB341_29465
SGMGCM10017557_20580
SFKKY5_8018c
SKACP970_43095
SVRCP971_33685
SSPBCP982_00540
SOVQZH56_31615
SFIYF0344_21150
KABB7C62_18880
KAUB6264_26755
SVISvir_33370
 » show all
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, Townsend CA.
  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
LinkDB

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
Brite
Enzymatic reactions [BR:br08201]
 2. Transferase reactions
  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
     R05465  D-Glyceraldehyde 3-phosphate + L-Arginine <=> L-N2-(2-Carboxyethyl)arginine + Orthophosphate
Orthology
K12673  N2-(2-carboxyethyl)arginine synthase [EC:2.5.1.66]
Other DBs
RHEA: 10559
LinkDB

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