Antibody-Catalyzed Enantioselective Epoxide Hydrolysis

Journal of the American Chemical Society

Volumn 115, Issue 11, 1993, Pages 4893-4894

  Sinha, Subhash C ^a   Keinan, Ehud ^a   Reymond, Jean Louis ^b  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000693982     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00064a061     Document Type: Article

References (22)

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13. B) Reymond, J.-L.; Janda, K. D.; Lerner, R. A. J. Am. Chem. Soc. 1992, 114, 2257.
14. c) Sinha, S. C.; Keinan, E.; Reymond, J.-L. J. Am. Chem. Soc., preceding communication in this issue,
15. d) Reymond, J.-L.; Jahangiri, G. K.; Stoudt, C.; Lerner, R. A. J. Am. Chem. Soc., in press.
16. An antibody-catalyzed formation of a tetrahydropyran ring from an epoxy alcohol has been recently reported: Janda, K. D.; Shevlin, C. G.; Lerner, R. A. Science 1993, 259, 490.
17. 4(Negishi, E.-I.; Matsushita, H.; Nobuhisa, O. Tetrahedron Lett. 1981, 22, 2715) to give (4-(methoxycarbonyl)phenyl)-l-cyclopentenylmethane;
18. N2-type attack of a chloride ion at the epoxide primary carbon (Addy, J. K.; Parker, R. E. J. Chem. Soc. 1965, 644). Its rate of formation increases linearly with NaCl concentration in both buffer solutions. Typically, at pH range of 5–6.5, 24 °C and 100 mM NaCl, both 5 and 8 are formed in comparable amounts.
19. 1H NMR signals related to the methyl carbinol group in the corresponding Mosher's esters: δS, 1.179; R, 1.166.
20. Using the asymmetric dihydroxylation reaction (a) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
21. 1H NMR signals related to the methyl carbinol group in the corresponding Mosher's monoester: δS, 1.168; R, 1.181. This level of enantiomeric purity may be increased by using benzyl instead of methyl esters and by recrystallizing the corresponding diols from cold diethyl ether. The diols were converted to the corresponding substrates 4S and 4R via a four-step sequence:
22. Jackson, D. Y.; Schultz, P. G. J. Am. Chem. Soc. 1991, 113, 2319.