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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

Full text
Author(s):
de Paula, Bruno R. S. ; Zampieri, Davila ; Rodrigues, J. Augusto R. ; Moran, Paulo J. S.
Total Authors: 4
Document type: Journal article
Source: TETRAHEDRON-ASYMMETRY; v. 28, n. 4, p. 545-549, APR 15 2017.
Web of Science Citations: 1
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 type: 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 type: Regular Research Grants