Synthesis of enantiomericalty pure 1,5,5-trideuterated cis- and trans-2,4-dioxa-3-phosphadecalins. 31P-NMR evidence of covalent-bond formation and the stereochemical implications in the course of the inhibition of δ-chymotrypsin

Helvetica Chimica Acta

Volumn 90, Issue 11, 2007, Pages 2058-2086

  Stöckli, Markus J ^a   Rüedi, Peter ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CHYMOTRYPSIN; COVALENT BOND FORMATION; IRREVERSIBLE INHIBITION;

COVALENT BONDS; ENANTIOMERS; ENZYME ACTIVITY; ENZYME INHIBITION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

CHYMOTRYPSIN INHIBITOR; DECALIN DERIVATIVE;

ARTICLE; CIS TRANS ISOMERISM; COVALENT BOND; DEUTERON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 36549047124     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200790215     Document Type: Article

References (41)

1. W. Ganci, E. J. M. Meier, F. Merckling, G. Przibille, U. Ringeisen, P. Rüedi, Helv. Chim. Acta 1997, 80, 421.
2. S. Furegati, W. Ganci, G. Przibille, P. Rüedi, Helv. Chim. Acta 1998, 81, 1127.
3. S. Furegati, W. Ganci, F. Gorla, U. Ringeisen, P. Rüedi, Helv. Chim. Acta 2004, 87, 2629.
4. S. Furegati, M. Binder, A. Linden, P. Rüedi, Helv. Chim. Acta 2006, 89, 1351, and refs. cit. therein.
5. M. J. Stöckli, P. Rüedi, Helv. Chim. Acta 2001, 84, 106.
6. J. Sanchez Real, J. Pascual, An. Fis. Quim., B 1953, 49, 445;
7. M. A. Febrer, P. Gomis, J. Pascual, An. Fis. Quim. 1964, 60, 671;
8. P. Gomis Torne, Rev. Real. Acad. Cienc. Exactas, Fis. Natur. Madrid 1966, 60, 419;
9. K. Chilina, U. Thomas, A. F. Tucci, K. D. Michael, C. M. Stevens, Biochemistry 1969, 8, 2846;
10. R. U. Lemieux, J. T. Brewer, Adv. Chem. Ser. 1973, 117, 121.
11. G. Przibille, Internal Progress Reports, University of Zurich, 1995, 1996;
12. S. Furegati, A. Linden, G. Przibille, D. Rentsch, P. Rüedi, '1st Electronic Conference on Synthetic Organic Chemistry' (ECSOC-1), 1-30 September 1997; http://unibas.ch/mdpi/ecsoc/a0034/a0034.htm.
13. M. Wächter, 'Herstellung optisch aktiver Organophosphate mit cis- und trans-Decalingerüst zur Untersuchung der Inhibition von Acetylcholinesterase', M. Sc. Thesis, University of Zurich, 2005.
14. N. K. Schaffer, C. S. May, W. H. Summerson, J. Biol. Chem. 1953, 202, 67;
15. D. M. Blow, J. J. Birktoft, B. S. Hartley, Nature 1969, 221, 337;
16. D. M. Blow, Acc. Chem. Res. 1976, 9, 145;
17. J. Kraut, Annu. Rev. Biochem. 1977, 46, 33;
18. P. A. Frei, S. A. Whitt, J. B. Tobin, Science 1981, 264, 1927;
19. T. A. Steitz, R. G. Shulman, Annu. Rev. Biophys. Bioeng. 1982, 11, 419;
20. L. Polgar, in 'Hydrolytic Enzymes', Eds. A. Neuenberger and K. Brocklehurst, Elsevier, Amsterdam, 1987.
21. F. Merckling, P. Rüedi, Tetrahedron Lett. 1996, 37, 2217.
22. G. R. J. Thatcher, R. Kluger, Adv. Phys. Org. Chem. 1989, 25, 99.
23. F. H. Westheimer, Acc. Chem. Res. 1968, 1, 70;
24. R. F. Hudson, C. Brown, Acc. Chem. Res. 1972, 5, 204;
25. P. Gillespie, F. Ramirez, I. Ugi, D. Marquarding, Angew. Chem., Int. Ed. 1973, 12, 109;
26. S. Tripett, Pure Appl. Chem. 1974, 40, 595.
27. F. Eckstein, P. J. Romaniuk, B. A. Connolly, Methods Enzymol. 1982, 87, 197;
28. S. A. Buchwald, D. E. Hansen, A. Hassett, J. R. Knowles, Methods Enzymol. 1982, 87, 279;
29. G. Lowe, Acc. Chem. Res. 1983, 16, 244.
30. R. Wolfenden, Acc. Chem. Res. 1972, 5, 10;
31. G. E. Lienhard, Science 1973, 180, 149;
32. R. Huber, W. Bode, Acc. Chem. Res. 1978, 11, 114;
33. A. Warshel, G. Naray-Szabo, F. Sussman, J. K. Hwang, Biochemistry 1989, 28, 3629.
34. N. S. Sampson, P. A. Bartlett, Biochemistry 1991, 30, 2255;
35. R. Bone, N. S. Sampson, P. A. Bartlett, D. A. Agard, Biochemistry 1991, 30, 2263.
36. C. M. Thomson, S. Ryu, C. E. Berkman, J. Am. Chem. Soc. 1992, 114, 10710.
37. R. F. Toia, J. E. Casida, Biochem. Pharmacol. 1979, 28, 3307;
38. A. C. M. van der Drift, H. C. Beck, W. H. Dekker, A. G. Hulst, E. R. J. Wils, Biochemistry 1985, 24, 6894;
39. J. Grunwald, Y. Segall, E. Shirin, D. Waysbort, N. Steinberg, I. Silman, Y. Ashani, Biochem. Pharmacol. 1989, 38, 3157.
40. C. A. Bunton, E. J. Fendler, J. H. Fendler, J. Am. Chem. Soc. 1967, 89, 1221.
41. C. J. Wilkins, J. Chem. Soc. 1951, 2726.