Convergence of catalytic antibody and terpene cyclase mechanisms: Polyene cyclization directed by carbocation - π interactions

Angewandte Chemie - International Edition

Volumn 38, Issue 12, 1999, Pages 1743-1747

  Paschall, Chiana M ^a   Hasserodt, Jens ^b   Jones, Terri ^b   Lerner, Richard A ^b   Janda, Kim D ^b   Christianson, David W ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Carbocations; Catalytic antibodies; Cyclases; Protein structures; Terpenoids

Indexed keywords

CATALYTIC ANTIBODY; HAPTEN; IMMUNOGLOBULIN F(AB) FRAGMENT; POLYENE; TERPENE; TERPENOID CYCLASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CYCLIZATION; ENZYME ACTIVE SITE; ENZYME MECHANISM; ENZYME SUBSTRATE; MOLECULAR INTERACTION; MOLECULAR STABILITY;

EID: 0033553805     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990614)38:12<1743::AID-ANIE1743>3.0.CO;2-3     Document Type: Article

References (47)

1. a) L. Ruzicka, Experientia 1953, 9, 357-367
2. (one of the six subheadings of this paper is entitled "Biogenesis of Steroids and Terpenic Compounds". Underneath Ruzicka adds a parenthetical comment "(together with A. Eschenmoser and H. Heusser)", along with a citation to Eschenmoser's PhD thesis (ETH Zürich, 1952));
3. b) J. W. Cornforth, Angew. Chem. 1968, 80, 977-985;
4. Angew. Chem. Int. Ed. Engl. 1968, 7, 903-911;
5. c) W. S. Johnson, Acc. Chem. Res. 1968, 1, 1-8;
6. d) D. Arigoni, Pure Appl. Chem. 1975, 41, 219-245;
7. e) D. E. Cane, Chem. Rev. 1990, 90, 1089-1103;
8. f) D. McCaskill, R. Croteau, Adv. Biochem. Eng. Biotechnol. 1997, 55, 107-146.
9. a) I. Abe, M. Rohmer, G. D. Prestwich, Chem. Rev. 1993, 93, 2189-2206;
10. b) C. Pale-Grosdemange, C. Feil, M. Rohmer, K. Poralla, Angew. Chem. 1998, 110, 2355-2358;
11. Angew. Chem. Int. Ed. 1998, 57, 2237-2240.
12. a) C. A. Lesburg, G. Zhai, D. E. Cane, D. W. Christianson, Science 1997, 277, 1820-1824;
13. b) C. M. Starks, K. Back, J. Chappell, J. P. Noel, Science 1997, 277, 1815-1820;
14. c) K. U. Wendt, K. Poralla, G. E. Schulz, Science 1997, 277, 1811-1815;
15. d) K. U. Wendt, G. E. Schulz, Structure 1998, 6, 127-133;
16. e) C. A. Lesburg, J. Caruthers, C. M. Paschall, D. W. Christianson, Curr. Opin. Struct. Biol. 1998, 8, 695-703.
17. a) S. K. Burley, G. A. Petsko, Adv. Protein Chem. 1988, 39, 125-189;
18. b) D. A. Dougherty, Science 1996, 271, 163-168;
19. c) C. Jenson, W. L. Jorgensen, J. Am. Chem. Soc. 1997, 119, 10846-10854;
20. d) J. C. Ma, D. A. Dougherty, Chem Rev. 1997, 97, 1303-1324.
21. a) P. G. Schultz, R. A. Lerner, Science 1995, 269, 1835-1842;
22. b) T. Li, R. A. Lerner, K. D. Janda, Acc. Chem. Res. 1997, 30, 115-121.
23. a) T. Li, K. D. Janda, J. A. Ashley, R. A. Lerner, Science 1994, 264, 1289-1293;
24. b) T. Li, S. Hilton, K. D. Janda, J. Am. Chem. Soc. 1995, 117, 3308-3309;
25. c) T. Li, K. D. Janda, R. A. Lerner, Nature 1996, 379, 326-327;
26. d) J. Hasserodt, K. D. Janda, R. A. Lerner, J. Am. Chem. Soc. 1996, 118, 11654-11655.
27. J. Hasserodt, K. D. Janda, R. A. Lerner, J. Am. Chem. Soc. 1997, 119, 5993-5998.
28. a) K. D. Janda, M. I. Weinhouse, D. M. Schloeder, R. A. Lerner, S. J. Benkovic, J. Am. Chem. Soc. 1990, 112, 1274-1275;
29. b) K. D. Janda, M. I. Weinhouse, T. Danon, K. A. Pacelli, D. M. Schloeder, J. Am. Chem. Soc. 1991, 113, 5427-5434.
30. M. I. Page, W. P. Jencks, Proc. Natl. Acad. Sci. USA 1971, 68, 1678-1683.
31. E. J. Corey, H. Cheng, C. H. Baker, S. P. T. Matsuda, D. Li, X. Song, J. Am. Chem. Soc. 1997, 119, 1277-1288.
32. a) W. S. Johnson, S. J. Telfer, S. Cheng, U. Schubert, J. Am. Chem. Soc. 1987, 109, 2517-2518;
33. b) W. S. Johnson, S. D. Lindell, J. Steele, J. Am. Chem. Soc. 1987, 109, 5852-5853.
34. J. Hasserodt, K. D. Janda, Tetrahedron 1997, 53, 11237-11256.
35. B. Seckler, K. Poralla, Biochim. Biophys. Acta 1986, 881, 356-363.
36. W. D. Huse, L. Sastry, S. A. Iverson, A. S. Kang, M. Alting-Mees, D. R. Burton, S. J. Benkovic, R. A. Lerner, Science 1989, 246, 1275-1281.
37. D. Radar, C. F. Barbas, Curr. Opin. Biotechnol. 1997, 8, 503-508.
38. C. F. Barbas, A. S. Kang, R. A. Lerner, S. J. Benkovic, Proc. Natl. Acad. Sci. USA 1991, 88, 7978-7982.
39. B. Gigant, J.-B. Charbonnier, Z. Eshhar, B. S. Green, M. Knossow, Proc. Natl. Acad. Sci. USA 1997, 94, 7857-7861.
40. J. Navaza, Acta Crystallogr. Sect. A 1994, 50, 157-163.
41. A. T. Brünger, J. Kuriyan, M. Karplus, Science 1987, 235, 458-460.
42. T. A. Jones, J.-Y. Zou, S. W. Cowan, M. Kjeldgaard, Acta. Crystallogr. Sect. A 1991, 47, 110-119.
43. Figures were prepared with MOLSCRIPT: P. Kraulis, J. Appl. Crystallogr. 1991, 24, 946-950;
44. Raster3D: D. J. Bacon, W. F. Anderson, J. Mol. Graphics 1988, 6, 219-220;
45. E. A. Merritt, M. E. P. Murphy, Acta Crystallogr. Sect. D 1994, 50, 869-873;
46. BOBSCRIPT: R. M. Esnouf, J. Mol. Graphics 1997, 15, 132-134;
47. GRASP: B. Honig, A. Nicholls, Science 1995, 268, 1144-1149.