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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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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Abstract 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.
AbstractList 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.
Author Itoh, T
Takagi, Y
Mitsukura, K
Kaihatsu, K
Tsukube, H
Hamada, H
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Keywords CANDIDA-RUGOSA LIPASE
SERINE PROTEASES
ENANTIOSELECTIVITY
CROWN-ETHERS
ORGANIC-SOLVENTS
ACYLATION
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Takagi, Y (WOS:A1996UW73900047) 1996; 37
MORIMOTO, T (WOS:A1994ND46600065) 1994; 42
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PALMER, DC (WOS:A1994NA42700014) 1994; 35
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Snippet 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...
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Physical Sciences
Science & Technology
Title 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
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