Substrate Modification as a Means of Enhancing the Enantioselectivity of Microbial Reductions of β-Keto Esters. An (R)- or (S)-1,3,5-Trihydroxypentane Synthon

Journal of Organic Chemistry

Volumn 52, Issue 2, 1987, Pages 192-196

  Brooks, Dee W ^a   Kellogg, Rosemary P ^a   Cooper, Curt S ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845283440     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00378a007     Document Type: Article

References (15)

1. For pertinent reviews of this topic refer to: (a) Enzymes in Organic Synthesis; Ciba Foundation Symposium III; Pitman: London, 1985. (b) Whitesides, G. M.; Wong, C. H. Aldrichimica Acta 1983,16,27. (c) Sih, C. J.; Rosaza, J. P. Applications of Biochemical Systems in Organic Chemistry; Jones, J. B., Sih, C. J., Perlman, D., Eds.; Wiley: New York, 1976; Part I.,Chapter III. (d) Kieslich, K. Microbial Transformations of Chemical Compounds Excluding Steroids and Noncyclic Structures; G. Thieme Verlag: Stuttgart, 1976.
2. For typical recent examples see: (a) Brooks, D. W.; Mazdiyasni, H.; Chakrabarti, S. Tetrahedron Lett. 1984, 25, 1241. (b) Akita, H.; Koshhi, H.; Furuichi, A.; Horikoshi, K.; Oishi, T. Tetrahedron Lett. 1983, 24, 2009. (c) Zueger, M. F.; Giovannin, F.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1983. 22. 1012.
3. Neuberg, C. Adv. Carbohydr. Chem. 1949, 4, 75. (b) MacLeod, R.; Prosser, H.; Fikentscher, L.; Lanyi, J.; Mosher, H. S. Biochemistry 1964, 3, 838. (c) Deol, B. S.; Ridley, D. D.; Simpson, G. W. Aust. J. Chem. 1976, 29, 2459. (d) Seebach, D.; Renaud, P.; Schweizer, W. B.; Zuger, M. F.; Brienne, M. J. Helv. Chim. Acta 1984, 67, 1843. (e) Nakamura, K.; Higaki, M.; Ushio, K.; Oka, S.; Ohno, A. Tetrahedron Lett. 1985, 26,4213.
4. The basic concepts determining enantioselectivity of enzymes and intact cells and strategies to control the stereochemical course of microbial reduction of carbonyl compounds is discussed by: Sih, C. J.; Chen, C. S. Angew. Chem., Int. Ed. Engl. 1984, 23, 570.
5. For a recent example see: Ushio, K.; Inouye, K.; Nakamura, K.; Oka, S.; Ohno, A. Tetrahedron Lett. 1986, 27, 2657.
6. Hirama, M.; Shimizu, M.; Iwashita, M. J. Chem. Soc., Chem. Commun. 1983, 599.
7. Zhou, B.; Gopalan, A. S.; Vanmiddlesworth, F.; Shieh, W. R.; Sih, C. J. J. Am. Chem. Soc. 1983, 105, 5925.
8. Brooks, D. W.; Castro de Lee, N.; Peevey, R. Tetrahedron Lett. 1984, 25, 4623.
9. Huckin, S. N.; Weiler, L. Can. J. Chem. 1974, 52, 2157.
10. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
11. Cohen, S. G.; Khedouri, J. J. Am. Chem. Soc. 1961, 83, 4228.
12. Our experience with chymotrypsin and related enzyme-catalyzed hydrolysis of esters is that optical yield is dependent on substrate concentration, temperature, and pH. For a detailed account, see: Lam, L. K. P.; Hui, R. A. H. F.; Jones, J. B. J. Org. Chem. 1986, 51, 2047. Also, the absolute value of the specific rotation observed for these products is variable depending on the concentration and solvent used and cannot be used as a reliable method of measuring optical purity as shown by: Rosen, T.; Watanabe, M.; Heathcock, C. H. J. Org. Chem. 1984, 49, 3657.
13. Brookes, M. H.; Golding, B. T.; Howes, D. A.; Hudson, A. T. J. Chem. Soc., Chem. Commun. 1983, 1051.
14. Guziec, F. S.; Luzzio, F. A. Synthesis 1980, 691.
15. Kuivila, H. G. Acc. Chem. Res. 1968, 1, 299.