The production of single enantiomers of γ and β-nitroalcohols by microbial bioreduction has been studied. A restricted screening among 14 yeasts was performed using 1-phenyl-4-nitro-1-butanone 1 as substrate. Pichia minuta (CBS 1708) and Pichia etchellsii (CBS 2011) gave the highest enantiopreference for (S)-alcohol 3 formation (e.e. 85% and 80%, respectively), while Kluyveromyces marxianus (CBS 397) was the only strain able to preferentially furnish the (R) enantiomer (e.e. 70%). These three microorganisms, along with baker's yeast, were then employed in reactions performed in water/organic solvent systems using different solvents (hexane, benzene and dibutyl ether) affording alcohol 3 in high enantiomeric excesses (>95-97%). These strains were also employed to reduce 1-phenyl-3-nitro-1- propanone 2, maintaining the same stereobias observed with γ-nitroketone 1 and showing high enantioselectivity in both simple aqueous (>85-97%) and biphasic media (>97%).

Microbial biotransformations in water/organic solvent system. Enantioselective reduction of aromatic β- and γ-nitroketones / E.G. Occhiato, F. Aragozzini, A. Guarna, F. Molinari. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 9:8(1998), pp. 1389-1394. [10.1016/S0957-4166(98)00096-2]

Microbial biotransformations in water/organic solvent system. Enantioselective reduction of aromatic β- and γ-nitroketones

F. Molinari
1998

Abstract

The production of single enantiomers of γ and β-nitroalcohols by microbial bioreduction has been studied. A restricted screening among 14 yeasts was performed using 1-phenyl-4-nitro-1-butanone 1 as substrate. Pichia minuta (CBS 1708) and Pichia etchellsii (CBS 2011) gave the highest enantiopreference for (S)-alcohol 3 formation (e.e. 85% and 80%, respectively), while Kluyveromyces marxianus (CBS 397) was the only strain able to preferentially furnish the (R) enantiomer (e.e. 70%). These three microorganisms, along with baker's yeast, were then employed in reactions performed in water/organic solvent systems using different solvents (hexane, benzene and dibutyl ether) affording alcohol 3 in high enantiomeric excesses (>95-97%). These strains were also employed to reduce 1-phenyl-3-nitro-1- propanone 2, maintaining the same stereobias observed with γ-nitroketone 1 and showing high enantioselectivity in both simple aqueous (>85-97%) and biphasic media (>97%).
Settore CHIM/11 - Chimica e Biotecnologia delle Fermentazioni
Settore CHIM/06 - Chimica Organica
TETRAHEDRON-ASYMMETRY
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/179376
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