KEGG   ENZYME: 4.2.1.27Help
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
BRITE hierarchy
Sysname
3-oxopropanoate hydro-lyase (propynoate-forming)
Reaction(IUBMB)
3-oxopropanoate = propynoate + H2O [RN:R01611]
Reaction(KEGG)
R01611;
(other) R01367
Show
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
beta-Alanine metabolism
Propanoate metabolism
Butanoate metabolism
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 (1985) 3155-3162.
Reference
2  [PMID:13654296]
  Authors
YAMADA EW, JAKOBY WB.
  Title
Enzymatic utilization of acetylenic compounds. II. Acetylenemonocarboxylic acid hydrase.
  Journal
J. Biol. Chem. 234 (1959) 941-5.
  Organism
Pseudomonas sp.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 
CAS: 
9024-26-4

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