Chiral induction in cyclopentyl-derived 1,3-meso-diesters: enantioselective hydrolyses with electric eel acetylcholinesterase

Tetrahedron Asymmetry

Volumn 10, Issue 11, 1999, Pages 2139-2152

  Deardorff, Donald R ^a   Amador, Roberto B ^a   Morton, James W ^a   Kim, Henry Y ^a   Taniguchi, Cullen M ^a   Balbuena, Arnel A ^a   Warren, Sam A ^a   Fanous, Vadim ^a   Choe, S W Tina ^a  

^a OCCIDENTAL COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCHOLINESTERASE; CYCLOPENTANE DERIVATIVE; ESTER DERIVATIVE;

ARTICLE; CHIRALITY; DRUG HYDROLYSIS; EEL; ELECTROPHORUS; ENANTIOMER; ENZYME MECHANISM; PARTIAL DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0033522727     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00236-0     Document Type: Article

References (24)

1. Deardorff, D. R.; Savin, K. A.; Justman, C. J.; Karanjawala, Z. E.; Sheppeck II, J. E.; Hager, D. C.; Aydin, N. J. Org. Chem. 1996, 61, 3616-3622.
2. Deardorff, D. R.; Matthews, A. J.; McMeekin, D. S.; Craney, C. L. Tetrahedron Lett. 1986, 1255-1256.
3. Deardorff, D. R.; Windham, C. Q.; Craney, C. L. Org. Synth. 1996, 73, 25-35.
4. Johnson, C. R.; Penning, T. D. J. Am. Chem. Soc. 1986, 108, 5655.
5. Pearson, A. J.; Bansal, H. S.; Lai, Y.-S. J. Chem. Soc., Chem. Commun. 1987, 519-520.
6. Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1991, 113, 5863-5864.
7. Schink, H. E.; Bäckvall, J.-E. J. Org. Chem. 1992, 57, 1588-1591.
8. Johnson, C. R.; Senanayake, C. H. J. Org. Chem. 1989, 54, 736-738.
9. Deardorff, D. R.; Myles, D. C.; MacFerrin, K. D. Tetrahedron Lett. 1985, 5615.
10. Deardorff, D. R.; Myles, D. C. Org. Synth. 1989, 67, 114-120.
11. Simmons, E. H.; Cairns, T. L.; Vladuchik, S. A.; Hoiness, C. M. Org. Reactions 1973, 20, 1-131.
12. Theil, F.; Schick, H.; Winter, G.; Reck, G. Tetrahedron 1991, 47, 7569-7582.
13. Alexakis, A.; Mutti, S.; Normant, J. F.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 437-440.
14. Deardorff, D. R.; Linde II, R. G.; Martin, A. M.; Shulman, M. J. J. Org. Chem. 1989, 54, 2759-2762.
15. Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1996, 118, 9526-9538.
16. The absolute configuration has been challenged by LeGrand, D. M.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1992, 1751-1752. Griffith and Danishefsky, however, reaffirm their confidence in this assignment in Ref. 15.
17. Radic, Z.; Pickering, N. A.; Vellom, D. C.; Camp, S.; Taylor, P. Biochemistry 1993, 32, 12074-12084.
18. Harel, M.; Sussman, J. L.; Krejci, E.; Bon, S.; Chanal, P.; Massoulie, J.; Silman, I. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 10827-10831.
19. Cox, P.; Newton, C.; Palfreyman, M. PCT Int. Appl. 106.
20. Borcherding, D.; Peet, N.; Munson, H.; Zhang, H.; Hoffman, P.; Bowlin, T.; Edwards, C. J. Med. Chem. 1996, 39, 2615-2620.
21. Takai, K.; Kakiuchi, T.; Utimoto, K. J. Org. Chem. 1994, 59, 2671-2673.
22. Smith, R. D.; Simmons, H. E. Org. Synth. 1973, Coll. Vol. 5, 855-858.
23. Laumen, K.; Schneider, M. Tetrahedron Lett. 1984, 25, 5875-5878.
24. Theil, F.; Schick, H.; Lapitskaya, M. A.; Pivnitskii, K. K. Liebigs Ann. Chem. 1991, 3, 195-200.