Baker's yeast: production of D- and L-3-hydroxy esters

Allan Carsten Dahl, Jørgen Øgaard Madsen

    Research output: Contribution to journalJournal articleResearchpeer-review


    Baker's yeast grown under oxygen limited conditions and used in the reduction of 3-oxo esters results in a shift of the stereoselectivity of the yeast towards D-hydroxy esters as compared with ordinary baker's yeast. The highest degree of stereoselectivity was obtained with growing yeast or yeast harvested while growing. In contrast, the stereoselectivity was shifted towards L-hydroxy esters when the oxo esters were added slowly to ordinary baker's yeast supplied with gluconolactone as co-substrate. The reduction rate with gluconolactone was increased by active aeration. Ethyl L-(S)-3-hydroxybutanoate was afforded in >99% ee. Both enantiomers of ethyl 3-hydroxypentanoate, D-(R) in 96% ee and L-(S) in 93% ee, and of ethyl 4-chloro-3-hydroxybutanoate, D-(S) in 98% ee and L-(R) in 94% ee, were obtained. The results demonstrate that the stereoselectivity of baker's yeast can be controlled to a large extent without the use of inhibitors, heat treatment, etc. (C) 1998 Elsevier Science Ltd. All rights reserved.
    Original languageEnglish
    JournalTetrahedron: Asymmetry
    Issue number24
    Pages (from-to)4395-4417
    Publication statusPublished - 1998


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