Biotransformation of electron-poor alkenes by yeasts: Asymmetric reduction of ( 4S)-(+)-carvone by yeast enoate reductases

Within the framework of a large-scale screening carried out on 146 yeasts of environmental origin, 16 strains (11% of the total) exhibited the ability to biotransform ( 4S)-(+)-carvone. Such positive yeasts, belonging to 14 species of 6 genera ( Candida, Cryptococcus, Hanseniaspora, Kluyveromyces, P...

Full description

Saved in:
Bibliographic Details
Published in:Enzyme and microbial technology 2009-12, Vol.45 (6), p.463-468
Main Authors: Goretti, Marta, Ponzoni, Chiara, Caselli, Elisa, Marchigiani, Elisabetta, Cramarossa, Maria Rita, Turchetti, Benedetta, Buzzini, Pietro, Forti, Luca
Format: Article
Language:English
Subjects:
( 4S)-(+)-carvone
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Biotransformation
Candida
Cryptococcus
Enoate reductase
Fundamental and applied biological sciences. Psychology
Hanseniaspora
Kluyveromyces
Methods. Procedures. Technologies
Pichia
Saccharomyces
Yeasts
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Within the framework of a large-scale screening carried out on 146 yeasts of environmental origin, 16 strains (11% of the total) exhibited the ability to biotransform ( 4S)-(+)-carvone. Such positive yeasts, belonging to 14 species of 6 genera ( Candida, Cryptococcus, Hanseniaspora, Kluyveromyces, Pichia and Saccharomyces), were thus used under different physiological state (growing, resting and lyophilised cells). Yields (expressed as% of biotransformation) varied from 0.14 to 30.04%, in dependence of both the strain and the physiological state of the cells. Products obtained from reduction of ( 4S)-(+)-carvone were 1S, 4S- and 1R, 4S-dihydrocarvone, ( 1S, 2S, 4S)-, ( 1S, 2R, 4S)- and ( 1R, 2S, 4S)-dihydrocarveol. Only traces of ( 1R, 2R, 4S)-dihydrocarveol were observed in a few strains. As far as the stereoselectivity of the biocatalysis, with the sole exception of a few strains, the use of yeasts determined the prevalent accumulation of 1S, 4S-isomers [( 1S, 4S)-dihydrocarvone + ( 1S, 2S, 4S)-dihydrocarveol + ( 1S, 2R, 4S)-dihydrocarveol]. The addition of glucose (acting as auxiliary substrate for cofactor-recycling system) to lyophilised yeast cells determined a considerable increase of biocatalytic activity: in particular, two strains showed a surprising increase of the% of biotransformation of ( 4S)-(+)-carvone (to values >98%).
ISSN:0141-0229
1879-0909
DOI:10.1016/j.enzmictec.2009.09.004