KEGG   ENZYME: 4.2.1.27
Entry
EC 4.2.1.27                 Enzyme                                 
Name
acetylenecarboxylate hydratase;
acetylenemonocarboxylate hydratase;
alkynoate hydratase;
acetylenemonocarboxylate hydrase;
acetylenemonocarboxylic acid hydrase;
malonate-semialdehyde dehydratase;
3-oxopropanoate hydro-lyase
Class
Lyases;
Carbon-oxygen lyases;
Hydro-lyases
Sysname
3-oxopropanoate hydro-lyase (propynoate-forming)
Reaction(IUBMB)
3-oxopropanoate = propynoate + H2O [RN:R01611]
Reaction(KEGG)
R01611;
(other) R01367
Substrate
3-oxopropanoate [CPD:C00222]
Product
propynoate [CPD:C00804];
H2O [CPD:C00001]
Comment
The reaction is effectively irreversible, favouring oxopropanoate (malonic semialdehyde) and its tautomers. Also acts on but-3-ynoate forming acetoacetate. The mechanism appears to involve hydration of the acetylene to 3-hydroxypropenoate, which will spontaneously tautomerize to 3-oxopropanoate. It is thus analogous to EC 4.1.1.78, acetylenedicarboxylate decarboxylase, in its mechanism.
History
EC 4.2.1.27 created 1965, (EC 4.2.1.71 created 1978, modified 1989, modified 2000, incorporated 2004) modified 2004
Pathway
ec00410  beta-Alanine metabolism
ec00640  Propanoate metabolism
ec00650  Butanoate metabolism
ec01100  Metabolic pathways
Reference
1
  Authors
Van den Tweel WJJ, De Bont JAM.
  Title
Metabolism of 3-butyn-1-ol by Pseudomonas BB1.
  Journal
J Gen Microbiol 131:3155-3162 (1985)
Reference
2  [PMID:13654296]
  Authors
YAMADA EW, JAKOBY WB.
  Title
Enzymatic utilization of acetylenic compounds. II. Acetylenemonocarboxylic acid hydrase.
  Journal
J Biol Chem 234:941-5 (1959)
Other DBs
ExplorEnz - The Enzyme Database: 4.2.1.27
IUBMB Enzyme Nomenclature: 4.2.1.27
ExPASy - ENZYME nomenclature database: 4.2.1.27
BRENDA, the Enzyme Database: 4.2.1.27
CAS: 9024-26-4

  All links  
Pathway (8)   
   KEGG PATHWAY (8)   
Chemical substance (5)   
   KEGG COMPOUND (5)   
Chemical reaction (4)   
   KEGG REACTION (2)   
   KEGG RCLASS (2)   
All databases (17)   

Download RDF
DBGET integrated database retrieval system