| Autor: |
Venkat Nanduri, David Brozozowski, Jeffrey M. Howell, Clyde G. McNamee, Ramesh N. Patel, David Mirfakhrae, Laszlo J. Szarka, John K. Thottathil, Amit Banerjee |
| Rok vydání: |
1993 |
| Předmět: |
|
| Zdroj: |
Tetrahedron: Asymmetry. 4:2069-2084 |
| ISSN: |
0957-4166 |
| DOI: |
10.1016/s0957-4166(00)82256-9 |
| Popis: |
The chiral intermediate (2R,3S)-(−)-N-benzoyl-3-phenyl isoserine ethyl ester 2a , a potential taxol 5 side-chain synthon, was prepared by microbial and enzymatic processes. Taxol 5 is an anticancer compound recently approved by FDA for the treatment of ovarian cancer. The stereoselective reduction of racemic 2-keto-3-(N-benzoylamino)-3-phenylpropionic acid ethyl ester 1 to the corresponding alcohol 2 was carried out using microbial cultures. Among microorganisms evaluated, Hansenula polymorpha SC 13865 and Hansenula fabianii SC 13894 effectively reduced compound 1 to the desired syn diastereomer 2a . Reaction yields of >80% and enantiomeric excesses of >98% were observed for these bioreduction process. About 10–20% of anti diastereomers ( 2c,2d ) were produced during bioreduction. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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