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Lipase‐Catalyzed Regioselective One‐Step Synthesis of Penta‐ O ‐acetyl‐3‐hydroxylactal
Author(s) -
Filice Marco,
Vanna Renzo,
Terreni Marco,
Guisan Jose M.,
Palomo Jose M.
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900357
Subject(s) - chemistry , rhizomucor miehei , regioselectivity , lipase , yield (engineering) , catalysis , hydrolysis , glycoconjugate , organic chemistry , acetylation , enzyme , triacylglycerol lipase , stereochemistry , combinatorial chemistry , biochemistry , materials science , metallurgy , gene
A highly efficient regioselective enzymatic preparation ofpenta‐ O ‐acetyl‐1,5‐anhydro‐2‐deoxy‐3‐hydroxy‐4‐ O ‐β‐galactopyranosyl‐ D ‐arabinohex‐1‐enitol has been successfully performed for the first time. This product was obtained in >99 % conversion (>95 % overall yield) by hydrolysis of per‐ O ‐acetylated lactal catalyzed by the lipase from Rhizomucor miehei immobilized on octylagarose. This molecule could be a potential building block for efficient synthesis of oligosaccharides or glycoconjugates.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)