Stereoselective reduction of 2-azido-1-phenylethanone derivatives by whole cells of marine-derived fungi applied to synthesis of enantioenriched beta-hydroxy-1,2,3-triazoles

Autor(es)

Alvarenga, Natalia ^[1] ; Porto, Andre L. M. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Quim Sao Carlos, Ave Joao Dagnone 1100, BR-13563120 Sao Carlos, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: BIOCATALYSIS AND BIOTRANSFORMATION; v. 35, n. 6, p. 388-396, 2017.
• Citações Web of Science: 1

Resumo

Several marine-derived fungi were evaluated by the bioreduction of 2-azido-1-phenylethanone 1, and the strains A. sydowii CBMAI 935 and M. racemosus CBMAI 847 were selected for the reduction of 2-azido-1-phenylethanone derivatives 2-4. Whole cells of A. sydowii CBMAI 935 promoted the reduction of 2-azido-1-phenylethanones 1-4 with high selectivities to yield the (S)-2-azido-1-phenylethanols 1a-4a. Bioreduction of compounds 1-4 by M. racemosus CBMAI 847 led to (R)-2azido-1-phenylethanols for 1, 2 and 4 and (S)-2-azido-1-phenylethanol 3. Enantiomerically enriched 2-azido-1-phenylethanols 1a-4a and phenylacetylene 5 were applied in the synthesis of b-hydroxy-1,2,3-triazoles using CuSO4 and sodium ascorbate leading to regioselective formation of enantioenriched 1,4-disubstituted 1,2,3-triazole compounds 1b-4b. (AU)

• Processo FAPESP: 14/18257-0 - Novas abordagens em reações biocatalíticas
• Beneficiário: Andre Luiz Meleiro Porto
• Modalidade de apoio: Auxílio à Pesquisa - Regular