Biotransformation of 3-azidomethy1-4-phenyl-3-buten-2-one and analogs by Saccharomyces cerevisiae: New evidence for an S(N)2 ' mechanism

Author(s)

de Paula, Bruno R. S. ; Zampieri, Davila ; Rodrigues, J. Augusto R. ; Moran, Paulo J. S.

• Document type: Journal article
• Source: TETRAHEDRON-ASYMMETRY; v. 28, n. 4, p. 5-pg., 2017-04-15.

Abstract

(Z)-3-XCH2-4-(C6H5)-3-buten-2-one enones (X = SCN, N-3, SO2Me, OC6H5) were synthesized and submitted to biotransformations using whole Saccharomyces cerevisiae cells. The enone (X = SCN) produced (R)-4-(phenyl)-3-methylbutan-2-one (R)-6 with 93% ee and enones (X = N-3, SO2Me, OC6H5) yielded a mixture of (R)-6 and the corresponding C=C bond reduction products. Biotransformation with enone (X = N3) mediated by Saccharomyces cerevisiae resulted in two products via two different routes: (i) the ketone (R)-4-azido-3-benzylbutan-2-one in 28% yield and with >99% ee by C=C bond reduction; (ii) ketone (R)-6 in 51% yield and with 95% ee via cascade reactions beginning with azido group displacement by the formal hydride from flavin mononucleotide in an S(N)2 ' type reaction followed by reduction of the newly formed C=C bond. (C) 2017 Elsevier Ltd. All rights reserved. (AU)

• FAPESP's process: 12/08385-6 - Study of enzymatic reductions of alpha,beta-unsaturated ketones, and their applications in the preparation of compounds of synthetic interest
• Grantee: Bruno Ricardo Silva de Paula
• Support Opportunities: Scholarships in Brazil - Doctorate
• 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