Premium
Studies on the Enzymatic Acylation of Quinic Acid, Shikimic Acid, Shikimic Acid, and Their Derivatives in Organic Solvents
Author(s) -
Danieli Bruno,
De Bellis Paolo,
Barzaghi Laura,
Carrea Giacomo,
Ottolina Gianluca,
Riva Sergio
Publication year - 1992
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19920750431
Subject(s) - chemistry , acylation , shikimic acid , lipase , quinic acid , organic chemistry , yield (engineering) , enzyme , regioselectivity , anthranilic acid , catalysis , materials science , metallurgy
Quinic acid ( 1a ), shikimic acid ( 2 ), and their derivatives were acylated in organic solvents by several lipases and by the protease subtilisin Carlsberg. The most satisfactory results were obtained with methyl (or benzyl) quinate ( 7a (or 8a )) and lipase from Chromobacterium viscosum adsorbed on Celite , which showed an overshelming preference towards the acylation of OH–C(4). Under optimized conditions, the syntehtically useful 4‐ O ‐acetylquinate 8d was isolated in ca. 90% yield. On the other hand, acylation of methyl shikimate ( 10a ) showed no regioselectivity with any of the enzymes tested. A possible rationale for the different behavior of Chromobacterium viscosum lipase towards 7a and 10a is given, comparing the conformations of these two molecules, as deducted from 1 H‐NMR and molecular‐mechanics calculation.