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, W.J.J. and De Bont, J.A.M.
  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

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

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