Asymmetric Reduction of Methyl 3-Oxopentanoate by Chlorella

概要

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Chlorella pyrenoidosa Chick catalyzed the reduction of methyl 3-oxopentanoate(Me 3-oxoPen)to the corresponding(S)-(+)-3-hydroxy ester in 60% enantiomeric excess(ee). An improvement of the ee of(S)-(+)-3-hydroxy ester was achieved by increasing substrate concentration and by the addition of 1% metal salts, namely, NaCl and KCl(75-78% ee). No shift of ee toward the(R)-(-)-3-hydroxy ester was observed following this addition. The addition of allyl alcohol brought about a decrease in both the chemical yields and the ee of(S)-(+)-3-hydorxy ester. Differences in the ability to reduce Me 3-oxoPen were observed among three strains of Chlorella, of which C.pyrenoidosa Chick yields the(S)-(+)-3-hydroxy ester but C.regularis and C.vulgaris Beijerinck yield(R)-(-)-enantiomer. In particular, C.regularis transformed Me 3-oxoPen to(R)-(-)-3-hudroxy ester in 79% ee, with a 10% yield.
公益社団法人日本生物工学会の論文
1998-04-25