KEGG   ENZYME: 4.2.1.166
Entry
EC 4.2.1.166                Enzyme                                 
Name
phosphinomethylmalate isomerase;
pmi (gene name)
Class
Lyases;
Carbon-oxygen lyases;
Hydro-lyases
Sysname
2-(phosphinomethyl)malate hydro-lyase [3-(phosphinomethyl)malate-forming]
Reaction(IUBMB)
2-(hydroxyphosphonoylmethyl)malate = 3-(hydroxyphosphonoylmethyl)malate (overall reaction) [RN:R11408];
(1a) 2-(hydroxyphosphonoylmethyl)malate = 2-(phosphinatomethylidene)butanedioate + H2O;
(1b) 2-(phosphinatomethylidene)butanedioate + H2O = 3-(hydroxyphosphonoylmethyl)malate
Reaction(KEGG)
R11408
Substrate
2-(hydroxyphosphonoylmethyl)malate;
2-(phosphinatomethylidene)butanedioate;
H2O [CPD:C00001]
Product
3-(hydroxyphosphonoylmethyl)malate;
2-(phosphinatomethylidene)butanedioate;
H2O [CPD:C00001]
Comment
The enzyme, characterized from the bacterium Streptomyces viridochromogenes, is involved in bialaphos biosynthesis. The enzyme from the bacterium Kitasatospora phosalacinea participates in the biosynthesis of the related compound phosalacine. Both compounds contain the nonproteinogenic amino acid L-phosphinothricin that acts as a potent inhibitor of EC 6.3.1.2, glutamine synthetase. The similar enzyme EC 4.2.1.3, aconitate hydratase, cannot catalyse this reaction.
History
EC 4.2.1.166 created 2016
Pathway
ec00440  Phosphonate and phosphinate metabolism
ec01110  Biosynthesis of secondary metabolites
Orthology
K20930  phosphinomethylmalate isomerase
Reference
1  [PMID:11472937]
  Authors
Heinzelmann E, Kienzlen G, Kaspar S, Recktenwald J, Wohlleben W, Schwartz D
  Title
The phosphinomethylmalate isomerase gene pmi, encoding an aconitase-like enzyme, is involved in the synthesis of phosphinothricin tripeptide in Streptomyces viridochromogenes.
  Journal
Appl Environ Microbiol 67:3603-9 (2001)
DOI:10.1128/AEM.67.8.3603-3609.2001
  Sequence
[ag:CAJ14040]
Other DBs
ExplorEnz - The Enzyme Database: 4.2.1.166
IUBMB Enzyme Nomenclature: 4.2.1.166
ExPASy - ENZYME nomenclature database: 4.2.1.166
BRENDA, the Enzyme Database: 4.2.1.166

  All links  
Pathway (4)   
   KEGG PATHWAY (4)   
Chemical substance (2)   
   KEGG COMPOUND (2)   
Chemical reaction (2)   
   KEGG REACTION (1)   
   KEGG RCLASS (1)   
Gene (2)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (1)   
All databases (10)   

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