Convenient enzymatic resolution of (R, S)‐2‐methylbutyric acid catalyzed by immobilized lipases. Issue 1 (30th October 2017)

• Record Type: Journal Article
• Authors: Mittersteiner, Mateus; Linshalm, Bruna Luiza; Vieira, Ana Paula Furlan; Brondani, Patrícia Bulegon; Scharf, Dilamara Riva; de Jesus, Paulo Cesar
• Is Part Of: Chirality. Volume 30:Issue 1(2018)
• Page Start: 106
• Page End: 111
• Publication Date: 2017-10-30
• Subjects: enantioselective esterification -- enzymatic acylation -- immobilized enzymes -- pheromones -- racemic acids; Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.22779
• Languages: English
• ISSNs: 0899-0042

Abstract

Abstract: 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%, eep 90%, and E = 35, while Thermomyces lanuginosus leads to c 18%, eep 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%, eep 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. Abstract :