Development of baker's yeast-mediated bioreduction for preparin of optically active glycidol derivatives

1992 Fiscal Year Final Research Report Summary

• Project/Area Number: 03556017
• Research Category: Grant-in-Aid for Developmental Scientific Research (B)
• Allocation Type: Single-year Grants
• Research Field: 製造化学・食品
• Research Institution: Toyama National College of Technology
• Principal Investigator: KITATSUJI Eitaro Toyama National College of Technology Industrial Chemistry, Professor, 物質工学科, 教授 (80019116)
• Co-Investigator(Kenkyū-buntansha): YOSHII Hidefumi Associate Professor, 物質工学科, 助教授 (60174885) ; KOMETANI Tadashi Associate Professor, 物質工学科, 助教授 (60042842) ; NISIMURA Hisataka Professor, 物質工学科, 教授 (10042805)
• Project Period (FY): 1991 – 1992
• Keywords: baker's yeast / assymetric reduction / optically active alcohol / selective oxidation / bubble-column reactor

Research Abstract

The baker's yeast-mediated bioreduction of prochiral ketones has been recognized as a useful technique for synthetic organic chemist. This research is to develop a procedure for preparing chiral secondary alcohol by yeast-mediated bioreduction.
Recently, we reported a new procedure for the yeast-mediated bioreduction using ethanol instead of sugar as the energy source. The new procedure is more efficient and clean than the original procedure, and it should be suitable for mass production.
1. Large-scale preparation of (S)-ethyl 3-hydroxybutanoate with a high enantiomeric excess through baker's yeast-mediated bioreduction The yeast-mediated bioreduction of ethyl acetoacetate by the new procedure was investigated to produce (S)-(+)-ethyl 3-hydroxybutanoate with high optical purity on a large scale. Improvements in the yield and the enantiomeric excess of the product were accomplished by applying the fed-batch operation to the procedure of the bioreduction. Then, a bubble-column reactor was chosen for the scale-up of the procedure. The reactor favorably underwent bioreduction in the large scale and the final reaction medium contained 6 % (w/w) (S)-ethyl 3-hydroxybutanoate with > 99 % ee.
2. Large-scale preparation of (R)-(-)-1,2-propanediol with a high enantiomeric excess through baker's yeast-mediated bioreduction (R)-(-)-1,2-Propanediol, deoxy derivative of glycidol, was produced by the yea st-mediated bioreduction of acetol through the same procedure mentioned above. (>99% ee, 300 g/L)
3. Preparation of (S-)(-)-1,2-propanediol (S)-(-)-1,2-Propanediol was obtained by treatment of (*)-1,2-propanediol with baker's yeast followed by removal of the acetol produced by selective oxidation of (R)-(-)-1,2-propanediol. The procedure is the new one on yeast-mediated preparation of chiral alcohols.