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Lipase Regioselective O ‐Acetylations of a myo ‐Inositol Derivative: Efficient Desymmetrization of 1,3‐Di‐ O ‐benzyl‐ myo ‐inositol
Author(s) -
Ribeiro Marcela F. P.,
Pais Karla C.,
de Jesus Barbara S. M.,
FernandezLafuente Roberto,
Freire Denise M. G.,
Manoel Evelin A.,
Simas Alessandro B. C.
Publication year - 2018
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.201701417
Subject(s) - desymmetrization , chemistry , regioselectivity , inositol , enantioselective synthesis , kinetic resolution , stereochemistry , trifluoromethanesulfonate , substrate (aquarium) , derivative (finance) , lipase , derivatization , organic chemistry , catalysis , enzyme , biochemistry , receptor , oceanography , high performance liquid chromatography , geology , financial economics , economics
Chiral myo ‐inositol derivatives play key roles in cell‐signaling processes. Despite the relevance of these compounds, few syntheses of them rely on enantioselective catalytic reactions. Even fewer reports describe the use of desymmetrization of myo ‐inositol derivatives. In fact, most routes involve resolution by derivatization. Thus, a symmetrical partially protected myo ‐inositol derivative, 1,3‐di‐ O ‐benzyl‐ myo ‐inositol ( 1 ), was used as a substrate in fast lipase‐catalyzed desymmetrization reactions. Among the lipases tested, both Lipozyme RM‐IM and Lipozyme TL‐IM were effective in catalyzing the formation of the chiral acetate l ‐(+)‐6‐ O ‐acetyl‐1,3‐di‐ O ‐benzyl‐ myo ‐inositol [ l ‐(+)‐ 2 ] with high conversion (98–99 %) and ee (>99 %). Conversely, Novozyme 435 and Lipomod 34P as biocatalysts showed different regioselectivity, leading to the formation of the symmetrical 5‐ O ‐acetylated product. We were able to reuse TL‐IM lipase seven times without any noticeable decrease in the conversion. Acetate l ‐(+)‐ 2 is a potential precursor of biologically active myo ‐inositol derivatives and other relevant materials for cell biology studies.