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Convenient enzymatic resolution of ( R , S )‐2‐methylbutyric acid catalyzed by immobilized lipases
Author(s) -
Mittersteiner Mateus,
Linshalm Bruna Luiza,
Vieira Ana Paula Furlan,
Brondani Patrícia Bulegon,
Scharf Dilamara Riva,
Jesus Paulo Cesar
Publication year - 2018
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22779
Subject(s) - chemistry , candida rugosa , candida antarctica , rhizopus oryzae , enantioselective synthesis , nucleophile , lipase , enantiomeric excess , catalysis , hexane , enantiomer , organic chemistry , solvent , chromatography , enzyme , fermentation
The application of several immobilized lipases has been explored in the enantioselective esterification of ( R , S )‐2‐methylbutyric acid, an insect pheromone precursor. With the use of Candida antarctica B, using hexane as solvent, ( R )‐pentyl 2‐methylbutyrate was prepared in 2 h with c 40%, ee p 90%, and E = 35, while Thermomyces lanuginosus leads to c 18%, ee p 91%, and E = 26. The ( S )‐enantiomer was obtained by the use of Candida rugosa or Rhizopus oryzae (2‐h reaction, c 34% and 35%, ee p 75 and 49%, and E = 10 and 4, respectively). Under optimal conditions, the effect of the solvent, the molar ratio, and the nucleophile were evaluated.