Reaction: 3-oxopropanoate = propynoate + H2O
Other name(s): acetylenemonocarboxylate hydratase; alkynoate hydratase; acetylenemonocarboxylate hydrase; acetylenemonocarboxylic acid hydrase; malonate-semialdehyde dehydratase; 3-oxopropanoate hydro-lyase
Systematic name: 3-oxopropanoate hydro-lyase (propynoate-forming)
Comments: 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 220.127.116.11, acetylenedicarboxylate decarboxylase, in its mechanism.
Links to other databases: BRENDA, EXPASY, KEGG, Metacyc, CAS registry number: 9024-26-4
1. Van den Tweel, W.J.J. and De Bont, J.A.M. Metabolism of 3-butyn-1-ol by Pseudomonas BB1. J. Gen. Microbiol. 131 (1985) 3155-3162. [PMID: 16525953]
2. Yamada, E.W. and Jakoby, W.B. Enzymatic utilization of acetylenic compounds. II. Acetylenemonocarboxylic acid hydrase. J. Biol. Chem. 234 (1959) 941-945. [PMID: 13654296]