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Acetylation of Racemic cis ‐ and trans ‐ α ‐Irols, Mediated by Porcine Pancreatic Lipase (PPL) − A New Route to (−) and (+)‐ cis ‐α‐Irone
Author(s) -
Aleu Josefina,
Bergamo Beatrice,
Brenna Elisabetta,
Fuganti Claudio,
Serra Stefano
Publication year - 2000
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 - 10.1002/1099-0690(200009)2000:17<3031::aid-ejoc3031>3.0.co;2-7
Subject(s) - chemistry , pancreatic lipase , acetylation , lipase , stereochemistry , biochemistry , organic chemistry , enzyme , gene
The mixture of the four racemic stereoisomers of α‐irol ( 5−8 ) was submitted to PPL‐mediated acetylation; cis ‐ α ‐irol 8b was converted more quickly than any other diastereoisomer and in enantiopure fashion. By chance, this latter derivative was the precursor of (−)‐ cis ‐α‐irone, the stereoisomer showing the strongest Orris butter character. Suitable manipulation of the material left unchanged by PPL provided (+)‐ cis ‐α‐irone. PPL’s mode of transformation of epoxy trans ‐ and cis ‐α‐irols was investigated, in order to ascertain the effect of chemical structure on the discriminating properties of this enzyme.