Ab initio study toward designing transition-state analogues which elicit proteolytic catalytic antibodies

Journal of Physical Organic Chemistry

Volumn 13, Issue 3, 2000, Pages 167-175

  Shimazaki, Kazuko ^a   Kakinuma, Hiroyuki ^a   Takahashi, Kyoko ^a   Niihata, Shigeo ^a   Takahashi, Naoko ^a   Matsushita, Hajime ^a   Nishi, Yoshisuke ^a   Sakakibara, Kazuhisa ^b  

^a JAPAN TOBACCO INC   (Japan)

^b YOKOHAMA NATIONAL UNIVERSITY   (Japan)

Author keywords

Catalytic antibody; Phosphonamidate; Proteolytic activity; Transition state analogue

Indexed keywords

EID: 0000226724     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1395(200003)13:3<167::AID-POC215>3.0.CO;2-M     Document Type: Article

References (33)

1. Pollack SJ, Jacobs JW, Schultz PG. Science 1986; 234: 1570-1573.
2. Tramantano A, Janda KD, Lerner RA. Science 1986; 234: 1566-1570.
3. Zhou G-W, Guo J, Huang W, Fletterick RJ, Scanlan TS. Science 1994; 265: 1059-1064.
4. Tawfik DS, Zemel RR, Arad-Yellin R, Green BS, Eshhar Z. Biochemistry 1990; 29: 9916-9921.
5. Charbonnier J-B, Carpenter E, Gigant B, G-Pimpaneau B, Eshhar Z, Green BS, Knossow M. Proc. Natl. Acad. Sci. USA 1995; 92: 11721-11725.
6. Janda KD, Schloeder D, Benkovic SJ, Lerner RA. Science 1988; 241: 1188-1191.
7. Stewart JD, Litta LJ, Benkovic SJ. Acc. Chem. Res. 1993; 26: 396-404.
8. Jacobs JW. Biotechnology 1991; 9: 258-262.
9. Pranata J. J. Phys. Chem. 1994; 98: 1180-1184.
10. O'Brien JF, Pranata J. J. Phys. Chem. 1995; 99: 12759-12763.
11. Hori K. J. Chem. Soc., Perkin Trans. 1992; 2: 1629-1633.
12. Hori K, Kamimura A, Ando K, Mizumura M, Ihara Y. Tetrahedron 1997; 53: 4317-4330.
13. Krug JP, Popelier PLA, Bader RFW. J. Phys. Chem. 1992; 96: 7604-7616.
14. Teraishi K, Saito M, Fujii I, Nakamura H. Tetrahedron Lett. 1992; 33: 7153-7156.
15. Tapia O, Paulino M, Stamato FMLG. Mol. Eng. 1994; 3: 377-414.
16. Kollman PA. Curr. Opin. Struct. Biol. 1992; 2: 765-771.
17. Scheiner S, Lipscomb WN. Proc. Natl. Acad. Sci. USA 1976; 73: 432-436.
18. Stamato FMLG, Longo E, Yoshioka LM, Ferreira RC. J. Theor. Biol. 1984; 107: 329-538.
19. Stamato FMLG, Tapia O. Int. J. Quantum. Chem. 1988; 33: 187-194.
20. Dive G, Dehareng D, Peeters D. Int. J. Quantum. Chem. 1996; 58: 85-107.
21. Weiner SJ, Seibel GL, Kollman PA. Proc. Natl. Acad. Sci. USA 1986; 83: 649-653.
22. Daggett V, Schröder S, Kollman P. J. Am. Chem. Soc. 1991; 113: 8926-8935.
23. Stanton RV, Peräkylä M, Bakowles D, Kollman PA. J. Am. Chem. Soc. 1998; 120: 3448-3457.
24. Fujinaga M, Sielecki AR, Read RJ, Ardelt W, Laskowski M, James MNG. J. Mol. Biol. 1987; 195: 397-418.
25. Komiyama M, Bender ML. Pro. Natl. Acad. Sci. USA, 1979; 76: 557-560.
26. Frisch MJ, Trucks GW, Schlegel HB, Gill PMW, Johnson BG, Robb MA, Cheeseman JR, Keith T, Petersson GA, Montgomery JA, Raghavachari K, Al-Laham MA, Zakrzewski VG, Ortiz JV, Foresman JB, Cioslowski J, Stefanov BB, Nanayakkara A, Challacombe M, Peng CY, Ayala PY, Chen W, Wong MW, Andres JL, Replogle ES, Gomperts R, Martin RL, Fox DJ, Binkley JS, Defrees DJ, Baker J, Stewart JP, Head-Gordon M, Gonzalez C, Pople JA. Gaussian 94. Revision D.4. Gaussian: Pittsburgh, PA, 1995.
27. Taira K, Gorenstein DG. Bull. Chem. Soc. Jpn. 1987; 60: 3625-3632.
28. Radkiewicz JL, McAllister MA, Goldstein E, Houk KN. J. Org. Chem. 1998; 63: 1419-1428.
29. Kakinuma H, Shimazaki K, Takahashi N, Takahashi K, Niihatu S, Aoki Y, Hamada K, Matsushita H, Nishi Y. Tetrahedron, 1999; 55: 2559-2572.
30. MacBeath G, Hilvert D. Chem. Biol. 1996; 3: 433-445.
31. Siuzdak G, Krebs JF, Benkovic SJ, Dyson HJ. J. Am. Chem. Soc. 1994; 116: 7937-7938.
32. Juaristi E, Cuevas G. The Anomeric Effect. CRC Press: Boca Raton, FL, 1995; 17-48.
33. Boys SF. Rev. Mod. Phys. 1960; 32: 296-299.