Deracemization of sec-Alcohols through Sequential Application of C. albicans and Ketoreductases

Author(s)

Nasario, Fabio D. ^[1] ; Moran, Paulo J. S. ^[1] ; Rodrigues, Jose Augusto R. ^[1]

Affiliation

^[1] Univ Estadual Campinas, Inst Quim, Dept Quim Organ, BR-13084971 Campinas, SP - Brazil

• Document type: Journal article
• Source: Journal of the Brazilian Chemical Society; v. 30, n. 4, p. 772-779, APR 2019.
• Web of Science Citations: 0

Abstract

A biocatalytic cascade process was developed using immobilized cells of the wild type yeast Candida albicans CCT 0776 in calcium alginate beads and a commercially available ketoreductase. The aim was to promote deracemization by stereoinversion of (±)-1-arylethanols in high substrate concentration (above 100 mmol L-1) to prepare the (R)-enantiomers of the alcohols (90-99%), with a high enantiomeric excess (83-99%) after 2 to 19 h. The (R)-1-(3-methoxyphenyl)ethanol, with 70% yield and 91% ee, obtained after 5 h was used to prepare (S)-1-(3-methoxyphenyl)-ethylamine with 60% yield and 91% ee after two steps, a key intermediate in the synthesis of (S)-rivastigmine. (AU)

• FAPESP's process: 16/12074-7 - Biocatalysis in Organic Synthesis Using Whole Cells of Microorganisms and Isolated Enzymes
• Grantee: José Augusto Rosário Rodrigues
• Support Opportunities: Regular Research Grants