Remarkable acceleration of a lipase-catalyzed reaction by a thiacrown ether additive: Buffer-free highly regioselective partial hydrolysis of 4-acetoxy-2-methylbut-2-enyl acetate

The reaction efficiency of the lipase-catalyzed partial hydrolysis of 4-acetoxy-2-methylbut-2-enyl acetate is greatly enhanced by the presence of 5 mol% of a thiacrown ether, particularly remarkable improvement being observed in CRL- and PCL-catalyzed reactions, 4-Hydroxy-2-methylbut-2-enyl acetate...

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Bibliographic Details
Published inJournal of the Chemical Society, Perkin Transactions 1 no. 16; pp. 2275 - 2278
Main Authors Itoh, T, Mitsukura, K, Kaihatsu, K, Hamada, H, Takagi, Y, Tsukube, H
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1997
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CANDIDA-RUGOSA LIPASE
SERINE PROTEASES
ENANTIOSELECTIVITY
CROWN-ETHERS
ORGANIC-SOLVENTS
ACYLATION
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Summary:The reaction efficiency of the lipase-catalyzed partial hydrolysis of 4-acetoxy-2-methylbut-2-enyl acetate is greatly enhanced by the presence of 5 mol% of a thiacrown ether, particularly remarkable improvement being observed in CRL- and PCL-catalyzed reactions, 4-Hydroxy-2-methylbut-2-enyl acetate has thus been simply prepared by buffer-free lipase-catalyzed hydrolysis.
ISSN:0300-922X
1364-5463
DOI:10.1039/a702894f