Stereoselective Bioreduction of α-Azido Ketones by Whole Cells of Marine-Derived Fungi.
Seven strains of marine-derived fungi (Aspergillus sclerotiorum CBMAI 849, Cladosporium cladosporioides CBMAI 857, Penicillium raistrickii CBMAI 931, Penicillium citrinum CBMA 1186, Mucor racemosus CBMAI 847, Beauveria felina CBMAI 738, and Penicillium oxalicum CBMAI 1185) and terrestrial fungus Penicillium chrysogenum CBMA1199 were screened as catalysts for the asymmetric reduction of α-keto azides 5-8 to their corresponding β-azidophenylethanols 9-12. The marine fungi showed Prelog and anti-Prelog selectivities to the reduction α-keto azides 5-8. The fungi A. sclerotiorum CBMAI 849, C. cladosporioides CBMAI 857, P. raistrickii CBMAI 931, and P. citrinum CBMA 1186 catalyzed the reduction of azido ketone 6 to the corresponding (R)-2-azido-1-(4-methoxyphenyl)ethanol (10) with good conversions (68-100 %) and excellent enantiomeric excesses (>99 % ee) according to Prelog rule.
Instituto de Química de São Carlos, Universidade de São Paulo, Av. João Dagnone, 1100, J. Santa Angelina, 13563-120, São Carlos, SP, Brazil.|Faculdade Ingá - Uningá, Rodovia PR 317, 6114, 87035-510, Maringá, PR, Brazil.
Lenilson C
LC
Rocha
Departamento de Ecologia e Biologia Evolutiva, Universidade Federal de São Carlos, Via Washington Luís, Km 235, 13565-905, São Carlos, SP, Brazil.
Mirna H R
MH
Seleghim
Universidade Federal de São Paulo, Rua Prof. Artur Riedel, 275 J. Eldorado, 09972-270, Diadema, SP, Brazil.
João V
JV
Comasseto
Divisão de Recursos Microbianos, Centro Pluridisciplinar de Pesquisas Químicas, Biológicas e Agrícolas, CPQBA, Universidade Estadual de Campinas, Rua Alexandre Casellato, 999, 13140-000, Paulínia, SP, Brazil.
Lara D
LD
Sette
Instituto de Química de São Carlos, Universidade de São Paulo, Av. João Dagnone, 1100, J. Santa Angelina, 13563-120, São Carlos, SP, Brazil. almporto@iqsc.usp.br.
André L M
AL
Porto
D059001:Aquatic Organisms / Q000378:metabolism*; D001230:Aspergillus / Q000378:metabolism; D001386:Azides / Q000378:metabolism*; D052982:Beauveria / Q000378:metabolism; D001673:Biodegradation, Environmental; D002384:Catalysis; D002963:Cladosporium / Q000378:metabolism; D005658:Fungi / Q000378:metabolism*; D007659:Ketones / Q000378:metabolism*; D009089:Mucor / Q000378:metabolism; D010407:Penicillium / Q000378:metabolism; D010408:Penicillium chrysogenum / Q000378:metabolism; D013237:Stereoisomerism
D001386:Azides; D007659:Ketones
Azido alcohols; Biocatalysis; Biotransformation; Marine fungi; Mycelia