Aldolase antibodies of remarkable scope

Journal of the American Chemical Society

Volumn 120, Issue 12, 1998, Pages 2768-2779

  Hoffmann, Torsten ^a   Zhong, Guofu ^a   List, Benjamin ^a   Shabat, Doron ^a   Anderson, James ^a   Gramatikova, Svetlana ^a   Lerner, Richard A ^a   Barbas III, Carlos F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODY; FRUCTOSE BISPHOSPHATE ALDOLASE;

ARTICLE; CATALYSIS; ENANTIOMER; ENZYME SPECIFICITY; ENZYME SUBSTRATE; ENZYME SYNTHESIS; NONHUMAN; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0032054562     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973676b     Document Type: Article

References (62)

1. For reviews of the aldol reaction, see: (a) Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3.
2. (b) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 12, 1.
3. (c) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
4. (d) Heathcock, C. H. Aldrichim. Acta 1990, 23, 99. Heathcock, C. H. Science 1981, 214, 395. Evans, D. A. Ibid. 1988, 240, 420. Masamune, S.; Choy, W.; Peterson, J.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1. Heathcock, C. H. et al. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, pp 133-319. Peterson, I. Pure Appl. Chem. 1992, 64, 1821.
5. (d) Heathcock, C. H. Aldrichim. Acta 1990, 23, 99. Heathcock, C. H. Science 1981, 214, 395. Evans, D. A. Ibid. 1988, 240, 420. Masamune, S.; Choy, W.; Peterson, J.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1. Heathcock, C. H. et al. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, pp 133-319. Peterson, I. Pure Appl. Chem. 1992, 64, 1821.
6. (d) Heathcock, C. H. Aldrichim. Acta 1990, 23, 99. Heathcock, C. H. Science 1981, 214, 395. Evans, D. A. Ibid. 1988, 240, 420. Masamune, S.; Choy, W.; Peterson, J.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1. Heathcock, C. H. et al. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, pp 133-319. Peterson, I. Pure Appl. Chem. 1992, 64, 1821.
7. (d) Heathcock, C. H. Aldrichim. Acta 1990, 23, 99. Heathcock, C. H. Science 1981, 214, 395. Evans, D. A. Ibid. 1988, 240, 420. Masamune, S.; Choy, W.; Peterson, J.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1. Heathcock, C. H. et al. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, pp 133-319. Peterson, I. Pure Appl. Chem. 1992, 64, 1821.
8. (d) Heathcock, C. H. Aldrichim. Acta 1990, 23, 99. Heathcock, C. H. Science 1981, 214, 395. Evans, D. A. Ibid. 1988, 240, 420. Masamune, S.; Choy, W.; Peterson, J.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1. Heathcock, C. H. et al. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, pp 133-319. Peterson, I. Pure Appl. Chem. 1992, 64, 1821.
9. (d) Heathcock, C. H. Aldrichim. Acta 1990, 23, 99. Heathcock, C. H. Science 1981, 214, 395. Evans, D. A. Ibid. 1988, 240, 420. Masamune, S.; Choy, W.; Peterson, J.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1. Heathcock, C. H. et al. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, pp 133-319. Peterson, I. Pure Appl. Chem. 1992, 64, 1821.
10. (d) Heathcock, C. H. Aldrichim. Acta 1990, 23, 99. Heathcock, C. H. Science 1981, 214, 395. Evans, D. A. Ibid. 1988, 240, 420. Masamune, S.; Choy, W.; Peterson, J.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1. Heathcock, C. H. et al. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, pp 133-319. Peterson, I. Pure Appl. Chem. 1992, 64, 1821.
11. (a) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.: Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319 and references therein. Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417 and references therein. Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871.
12. (a) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.: Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319 and references therein. Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417 and references therein. Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871.
13. (a) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.: Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319 and references therein. Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417 and references therein. Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871.
14. (b) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649.
15. (a) Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443.
16. (b) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 412-432.
17. (b) Henderson, I.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 558.
18. (c) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994. Bednarski, M. D. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, p 455. Gijsen, H. J. M., Wong, C.-H. Ibid. 1995, 117, 2947. Wong, C.-H. et al. Ibid. 1995, 117, 3333. Chen, L.; Dumas, D. P.; Wong, C.-H. Ibid. 1992, 114, 741.
19. (c) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994. Bednarski, M. D. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, p 455. Gijsen, H. J. M., Wong, C.-H. Ibid. 1995, 117, 2947. Wong, C.-H. et al. Ibid. 1995, 117, 3333. Chen, L.; Dumas, D. P.; Wong, C.-H. Ibid. 1992, 114, 741.
20. (c) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994. Bednarski, M. D. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, p 455. Gijsen, H. J. M., Wong, C.-H. Ibid. 1995, 117, 2947. Wong, C.-H. et al. Ibid. 1995, 117, 3333. Chen, L.; Dumas, D. P.; Wong, C.-H. Ibid. 1992, 114, 741.
21. (c) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994. Bednarski, M. D. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, p 455. Gijsen, H. J. M., Wong, C.-H. Ibid. 1995, 117, 2947. Wong, C.-H. et al. Ibid. 1995, 117, 3333. Chen, L.; Dumas, D. P.; Wong, C.-H. Ibid. 1992, 114, 741.
22. (c) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994. Bednarski, M. D. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, p 455. Gijsen, H. J. M., Wong, C.-H. Ibid. 1995, 117, 2947. Wong, C.-H. et al. Ibid. 1995, 117, 3333. Chen, L.; Dumas, D. P.; Wong, C.-H. Ibid. 1992, 114, 741.
23. (a) Wagner, J.; Lerner, R. A.; Barbas III, C. F. Science 1995, 270, 1797.
24. (b) Zhong, G.; Hoffmann, T.; Lerner, R. A.; Danishefsky, S.; Barbas III, C. F. J. Am. Chem. Soc. 1997, 119, 8131.
25. (c) Barbas III, C. F.; Heine, A.; Zhong, G.; Hoffmann, T.; Gramatikova, S.; Björnestedt, R.; List, B.; Anderson, J.; Stura, E. A.; Wilson, E. A.; Lerner, R. A. Science 1997, 278, 2085.
26. Björnestedt, R.; Zhong, G.; Lerner, R. A.; Barbas III, C. F. J. Am. Chem. Soc. 1996, 118, 11720.
27. Hupe, D. J.; Kendall, M. C. R.; Spencer, T. A. J. Am. Chem. Soc. 1973, 95, 2271.
28. Baldwin, J. E.; Lusch, M. J. Tetrahedron 1982, 38, 2939.
29. Dickens, J. C.; Gutman, A.; Payne, T. L.; Ryker, L. C.; Rudinsky, J. A. J. Chem. Ecol. 1983, 9, 1383. Libbey, L. M.; Oehlschlager, A. C.; Ryker, L. C. J. Chem. Ecol. 1983, 9, 1533.
30. Dickens, J. C.; Gutman, A.; Payne, T. L.; Ryker, L. C.; Rudinsky, J. A. J. Chem. Ecol. 1983, 9, 1383. Libbey, L. M.; Oehlschlager, A. C.; Ryker, L. C. J. Chem. Ecol. 1983, 9, 1533.
31. Paterson, I.; Goodman, J. M.; Lister, M. A.; Schumann, C.; McClure, C. K.; Norcross, R. D. Tetrahedron 1990, 46, 4663.
32. (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. Walsh, P. J., Sharpless, K. B. Synlett 1993, 605.
33. (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. Walsh, P. J., Sharpless, K. B. Synlett 1993, 605.
34. Barbas III, C. F., Wang, Y.-F., Wong, C.-H. J. Am. Chem. Soc. 1990, 112, 2013.
35. Welch, J. T.; Seper, K.; Eswarakrishnan, S.; Samartino, J. J. Org. Chem. 1984, 49, 4720. House, H. O.; Fischer, W. F.; Gall, M.; McLaughlin, T. E.; Peet, N. P. J. Org. Chem. 1971, 36, 3429-3437. Kowalski, C.; Creary, X.; Rollin, A. J.; Burke, M. C. J. Org. Chem. 1978, 43, 2601.
36. Welch, J. T.; Seper, K.; Eswarakrishnan, S.; Samartino, J. J. Org. Chem. 1984, 49, 4720. House, H. O.; Fischer, W. F.; Gall, M.; McLaughlin, T. E.; Peet, N. P. J. Org. Chem. 1971, 36, 3429-3437. Kowalski, C.; Creary, X.; Rollin, A. J.; Burke, M. C. J. Org. Chem. 1978, 43, 2601.
37. Welch, J. T.; Seper, K.; Eswarakrishnan, S.; Samartino, J. J. Org. Chem. 1984, 49, 4720. House, H. O.; Fischer, W. F.; Gall, M.; McLaughlin, T. E.; Peet, N. P. J. Org. Chem. 1971, 36, 3429-3437. Kowalski, C.; Creary, X.; Rollin, A. J.; Burke, M. C. J. Org. Chem. 1978, 43, 2601.
38. Iriye, R.; Takai, K.; Noguchi, M. Bioorg. Med. Chem. Lett. 1997, 7, 199. Konieczny, M. T.; Toma, P. H.; Cushman, M. J. Org. Chem. 1993, 58, 4619.
39. Iriye, R.; Takai, K.; Noguchi, M. Bioorg. Med. Chem. Lett. 1997, 7, 199. Konieczny, M. T.; Toma, P. H.; Cushman, M. J. Org. Chem. 1993, 58, 4619.
40. Reymond, J.-L.; Chen, Y. J. Org. Chem. 1995, 60, 6979.
41. Reymond, J.-L. Angew. Chem., Int. Ed. Engl. 1995, 34, 2285.
42. Dean, J. A. In Lange's Handbook of Chemistry; McGraw-Hill: San Francisco, CA, 1992; pp 8.19-8.71.
43. Hupe, D. J.; Kendall, M. C. R.; Spencer, T. A. J. Am. Chem. Soc. 1972, 94, 1254.
44. Westheimer, F. H. Proceeding of the Robert A. Welch Found. Conf. Chem. Res. 1971, 15, 7. Westheimer, F. H. Tetrahedron 1995, 51, 3. Highbarger, L. A.; Gerlt, J. A.; Kenyon, G. L. Biochemistry 1996, 35, 41.
45. Westheimer, F. H. Proceeding of the Robert A. Welch Found. Conf. Chem. Res. 1971, 15, 7. Westheimer, F. H. Tetrahedron 1995, 51, 3. Highbarger, L. A.; Gerlt, J. A.; Kenyon, G. L. Biochemistry 1996, 35, 41.
46. Westheimer, F. H. Proceeding of the Robert A. Welch Found. Conf. Chem. Res. 1971, 15, 7. Westheimer, F. H. Tetrahedron 1995, 51, 3. Highbarger, L. A.; Gerlt, J. A.; Kenyon, G. L. Biochemistry 1996, 35, 41.
47. Reichardt, C. In Solvents and Solvents Effects in Organic Chemistry, 2nd ed.; Ebel, H. F., Wentrup-Byne, E., Eds.; New York, 1990; pp 1-511. Heathcock, C. H. Stereoselective Aldol Condensations. In Comprehensive Carbanion Chemistry; Buncel, E., Durst, T., Eds.; Elsevier: Amsterdam, 1984: part B, p 177ff (particularly p 198).
48. Reichardt, C. In Solvents and Solvents Effects in Organic Chemistry, 2nd ed.; Ebel, H. F., Wentrup-Byne, E., Eds.; New York, 1990; pp 1-511. Heathcock, C. H. Stereoselective Aldol Condensations. In Comprehensive Carbanion Chemistry; Buncel, E., Durst, T., Eds.; Elsevier: Amsterdam, 1984: part B, p 177ff (particularly p 198).
49. Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207. For a general review including experimental procedures, see: Whitesell, J. K., Whitesell, M. A. Synthesis 1983, 517-536.
50. Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207. For a general review including experimental procedures, see: Whitesell, J. K., Whitesell, M. A. Synthesis 1983, 517-536.
51. Lucero, M. J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 826. For leading references, see: Pfau, M.; Revial, G.; Guingant, A.; d'Angelo, J. J. J. Am. Chem. Soc. 1985, 107, 273. d'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1995, 6, 1795. Cavé, C.; Desmaële, D.; d'Angelo, J. J. Org. Chem. 1996, 61, 4361.
52. Lucero, M. J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 826. For leading references, see: Pfau, M.; Revial, G.; Guingant, A.; d'Angelo, J. J. J. Am. Chem. Soc. 1985, 107, 273. d'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1995, 6, 1795. Cavé, C.; Desmaële, D.; d'Angelo, J. J. Org. Chem. 1996, 61, 4361.
53. Lucero, M. J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 826. For leading references, see: Pfau, M.; Revial, G.; Guingant, A.; d'Angelo, J. J. J. Am. Chem. Soc. 1985, 107, 273. d'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1995, 6, 1795. Cavé, C.; Desmaële, D.; d'Angelo, J. J. Org. Chem. 1996, 61, 4361.
54. Lucero, M. J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 826. For leading references, see: Pfau, M.; Revial, G.; Guingant, A.; d'Angelo, J. J. J. Am. Chem. Soc. 1985, 107, 273. d'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1995, 6, 1795. Cavé, C.; Desmaële, D.; d'Angelo, J. J. Org. Chem. 1996, 61, 4361.
55. Lucero, M. J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 826. For leading references, see: Pfau, M.; Revial, G.; Guingant, A.; d'Angelo, J. J. J. Am. Chem. Soc. 1985, 107, 273. d'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1995, 6, 1795. Cavé, C.; Desmaële, D.; d'Angelo, J. J. Org. Chem. 1996, 61, 4361.
56. Lin, J.-F.; Wu; C.-C.; Lien, M.-H. J. Phys. Chem. 1995, 99, 16903.
57. List, B.; Shabat, D.; Barbas III, C. F.; Lerner, R. A. Chem. Eur. J. In press.
58. Zhong, G. et al., submitted.
59. Hiatt, A. Nature 1990, 334, 469. Hiatt, A.; Ma, J. K. Int. Rev. Immunol. 1993, 10, 139. Ma, J. K.; Hiatt, A.; Hein, M.; Vine, N. D.; Wang, F.; Stabila, P.; van Dolleweerd, C.; Mostov, K.; Lehner, T. Science 1995, 268, 716. Franken, E.; Teuschel, U.; Hain, R. Curr. Opin. Biotechnol. 1997, 8, 411.
60. Hiatt, A. Nature 1990, 334, 469. Hiatt, A.; Ma, J. K. Int. Rev. Immunol. 1993, 10, 139. Ma, J. K.; Hiatt, A.; Hein, M.; Vine, N. D.; Wang, F.; Stabila, P.; van Dolleweerd, C.; Mostov, K.; Lehner, T. Science 1995, 268, 716. Franken, E.; Teuschel, U.; Hain, R. Curr. Opin. Biotechnol. 1997, 8, 411.
61. Hiatt, A. Nature 1990, 334, 469. Hiatt, A.; Ma, J. K. Int. Rev. Immunol. 1993, 10, 139. Ma, J. K.; Hiatt, A.; Hein, M.; Vine, N. D.; Wang, F.; Stabila, P.; van Dolleweerd, C.; Mostov, K.; Lehner, T. Science 1995, 268, 716. Franken, E.; Teuschel, U.; Hain, R. Curr. Opin. Biotechnol. 1997, 8, 411.
62. Hiatt, A. Nature 1990, 334, 469. Hiatt, A.; Ma, J. K. Int. Rev. Immunol. 1993, 10, 139. Ma, J. K.; Hiatt, A.; Hein, M.; Vine, N. D.; Wang, F.; Stabila, P.; van Dolleweerd, C.; Mostov, K.; Lehner, T. Science 1995, 268, 716. Franken, E.; Teuschel, U.; Hain, R. Curr. Opin. Biotechnol. 1997, 8, 411.