Selectivity with Catalytic Antibodies - What Can Be Achieved?

Catalytic Antibodies

Volumn , Issue , 2005, Pages 370-417

  Gouverneur, Veronique ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Acyl transfer reactions; Additions; Aldol reactions; Catalytic antibodies; Cyclization; Eliminations; Glycosyl group transfer; Pericyclic reactions; Phosphoryl group transfer; Selectivity with catalytic antibodies

Indexed keywords

CYCLIZATION; KETONES;

ACYL TRANSFER REACTION; ADDITIONS; ALDOL REACTIONS; CATALYTIC ANTIBODIES; ELIMINATIONS; GLYCOSYL GROUP; PERICYCLIC REACTION; PHOSPHORYL GROUP TRANSFER;

ANTIBODIES;

EID: 85018193587     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/3527603662.ch14     Document Type: Chapter

References (148)

1. Keinan, E., Sinha, S. C., Shabat, D., Itzhaky, H., Reymond, J.-L., "Asymmetric Organic Synthesis with Catalytic Antibodies", Acta Chem. Scand. 50 (1996), p. 679-687
2. Hasserodt, J., "Organic Synthesis Supported by Antibody Catalysis", Synlett 12 (1999), p. 2007-2012
3. Hilvert, D., "Stereoselective Reactions with Catalytic Antibodies", Top. Stereochem. 22 (1999), p. 83-135
4. Stevenson, J. D., Thomas, N. R., "Catalytic antibodies and other biomimetic catalysts", Nat. Prod. Rep. 17 (2000), p. 535-577
5. Thomas, N. R., "Catalytic Antibodies - Reaching Adolescence?", Nat. Prod. Rep. 17 (1996), p. 479-511
6. Blackburn, G. M., Garcon, A., "Catalytic Antibodies", Biotechnology (2000), p. 403-490.
7. Pollack, S. J., Jacobs, J. W., Schultz, P. G., "Selective chemical catalysis by an antibody", Science 234 (1986), p. 1570
8. Janda, K. D., Schloeder, D., Benkovic, S. J., Lerner, R. A., "Induction of an antibody that catalyzes the hydrolysis of an amide bond", Science 241 (1988), p. 1188-1191
9. Brummer, O., Wentworth P. Jr., Weiner, D. P., Janda, K. D., "Phosphorodithioates: synthesis and evaluation of new haptens for the generation of antibody acyl transferases", Tetrahedron Lett. 40 (1999), p. 7307-7310
10. Benedetti, F., Berti, F., Colombatti, A., Ebert, C., Linda, P., Tonizzo, F., "Anti-sulfonamide antibodies catalyze the hydrolysis of a heterocyclic amide", J. Chem. Soc. Chem. Commun. (1996), p. 1417-1418
11. Kitazume, T., Tsukamoto, T., Yoshimura, K., "A catalytic antibody elicited by a hapten of tetrahedral carbon-type", J. Chem. Soc. Chem. Commun. (1994), p. 1355.
12. Shokat, K. M., Ko, K. M., Scanlan, T. S., Kochesperger, L., Yonkovich, S., Thaisrivongs, S., Schultz, P. G, "Catalytic antibodies: a new class of transition-state analogs to produce hydrolytic antibodies", Angew. Chem. Int. Ed. Engl. 29 (1990), p. 1296
13. Tantillo, D. J., Houk, K. N., "Canonical binding arrays as molecular recognition elements in the immune system: tetrahedral anions and the ester hydrolysis transition state", Chem. Biol. 8(6) (2001), p. 535-545
14. Tantillo, D. J., Houk, K. N., "Fidelity in Hapten Design: How Analogous Are Phosphonate Haptens to the Transition States of Alkaline Hydrolyzes of Aryl Esters", J. Org. Chem. 64 (1999), p. 3066-3076
15. Janda, K. D., Weinhouse, M. I., Schloeder, D. M., Lerner, R. A., Benkovic, S. J., "Bait and switch strategy for obtaining catalytic antibodies with acyl-transfer capabilities", J. Am. Chem. Soc. 112 (1990), p. 1274-1275
16. Janda, K. D., Weinhouse, M. I., Danon T., Pacelli, K. A., Schloeder, D. M., "Antibody bait and switch catalysis: a survey of antigens capable of inducing antibodies with acyl-transfer properties", J. Am. Chem. Soc. 113 (1991), p. 5427-5434
17. Saga, H., Ersoy, O., Williams, S. F., Tsumuraya, T., Margolies, M. N., Sinskey, A. J., Masamune, S., "Catalytic antibodies generated via heterologous immunization", J. Am. Chem. Soc. 116 (1994), p. 6025-6026
18. Tsumuraya, T., Saga, H., Meguro, S., Tsunakawa, A., Masamune, S., "Catalytic Antibodies Generated via Homologous and Heterologous Immunization", J. Am. Chem. Soc. 117 (1995), p. 11390-11396
19. Wirsching, P., Ashley, J. A., Lo, C.-H. L., Janda, K. D., Lerner, R. A., "Reactive immunization", Science 270 (1995), p. 1775-1782
20. Grynszpan, F., Keinan, E., "Use of antibodies to dissect the components of a catalytic event. The cyclopropenone hapten", Chem. Commun. 8(1998), p. 865-866
21. Janda, K. D., Benkovic, S. J., Lerner, R. A., "Catalytic antibodies with lipase activity and R or S substrate selectivity", Science 244 (1989), p. 437-440
22. Pollack, S. J., Hsiun, P., Schultz, P. G., "Stereospecific Hydrolysis of Alkyl Esters by Antibodies", J. Am. Chem. Soc. 111 (1989), p. 5961-5962
23. Lo, C-H. L., Wentworth, P., Jung, K. W., Yoon, J., Ashley, J. A., Janda, K. D., "Reactive Immunization Strategy Generates Antibodies with High Catalytic Proficiencies", J. Am. Chem. Soc. 119 (1997), p. 10251-10252
24. Datta, A., Wentworth, P., Shaw, J. P., Simeonov, A., Janda, K. D., "Catalytically Distinct Antibodies Prepared by the Reactive Immunization versus Transition State Analog Hapten Manifolds", J. Am. Chem. Soc. 121 (1999), p. 10461-10467
25. Guo, J., Huang, W., Scanlan, T. S, "Kinetic and Mechanistic Characterization of an Efficient Hydrolytic Antibody: Evidence for the Formation of an Acyl Intermediate", J. Am. Chem. Soc. 116 (1994), p. 6062-6069
26. Zhou, G. W., Guo, J., Huang, W., Fletterick, R. J., Scanlan, T. S., "Crystal structure of a catalytic antibody with a serine pro-tease active site", Science 265 (1994), p. 1059-1064
27. Wade, H., Scanlan, T. S., "P1-S1 Interactions Control the Enantioselectivity and Hydrolytic Activity of the Norleucine Phenylesterase Catalytic Antibody 17E8", J. Am. Chem. Soc. 118 (1996), p. 6510-6511
28. Kitazume, T., Lin, J. T., Takeda, M., Yamazaki, T., "Stereoselective Synthesis of Fluorinated Materials Catalyzed by an Antibody", J. Am. Chem. Soc. 113 (1991), p. 2123-2126
29. Kitazume, T., Lin, J. T., Yamamoto, T., Yamazaki, T., "Antibody-Catalyzed Double Stereoselection in Fluorinated Materials", J. Am. Chem. Soc. 137 (1991), p. 8573-8575
30. Iwabuchi, Y., Miyashita, H., Tanimura, R., Kinoshita, K., Kikuchi, M., Fujii, I., "Regio- and Stereoselective Deprotection of Acylated Carbohydrates via Catalytic Antibodies", J. Am. Chem. Soc. 116 (1994), p. 771-772
31. Tanaka, F., Kinoshita, K., Tanimura, R., Fujii, I., "Relaxing Substrate Specificity in Antibody-Catalyzed Reactions: Enantioselective Hydrolysis of N-Cbz-Amino Acid Esters", J. Am. Chem. Soc. 118 (1996), p. 2332-2339
32. Li, T., Hilton, S., Janda, K. D., "The Potential Application of Catalytic Antibodies to Protecting Group Removal: Catalytic Antibodies with Broad Substrate Tolerance", J. Am. Chem. Soc. 117 (1995), p. 2123-2127
33. Kurihara, S., Tsumuraya, T., Susuki, K., Kuroda, M., Liu, L., Takaoka, Y., Fujii, I., "Antibody-Catalyzed Removal of the p-Nitrobenzyl Ester Protecting Group: The Molecular Basis of Broad Substrate Specificity", Chem. Eur. J. 6(9) (2000), p. 1656-1662
34. Wong, CH., Whitesides, G. M., "Enzymes in Synthetic Organic Chemistry", Tetrahedron Organic Chemistry Series Volume 12 (1994), p. 41-130
35. Shoji, I., Weinhouse, M. I., Janda, K. D., Lerner, R. A., Danishefsky, S. J., "Asymmetric induction via a catalytic antibody", J. Am. Chem. Soc. 113 (1990), p. 7763-7764
36. Fernholz, E., Schloeder, D., Liu, K.-C., Bradshaw, C. W., Huang, H., Janda, K., Lerner, R. A., Wong, C.-H., "Specificity of Antibody-Catalyzed Transesterifications Using Enol Ethers: A Comparison with Lipase Reactions", J. Org. Chem. 57 (1992), p. 4756-4761
37. Jacobsen, J. R., Prudent, J. R., Kochersperger, L., Yonkovich, S., Schultz, P. G., "An efficient antibody-catalyzed aminacylation reaction", Science 256 (1992), p. 365-367
38. Hirschmann, R., Smith III, A. B., Taylor, C. M., Benkovic, P. A., Taylor, C. M., Yager, K. M., Witherington, J., Philips, B. W., Sprengler, P. A., Benkovic, S. J., "Peptide synthesis catalyzed by an antibody containing a binding site for variable amino acids", Science 265 (1994), p. 234-237
39. Napper, A. D., Benkovic, S. J., Tramontano, A., Lerner, R. A., "A stereospecific cyclization catalyzed by an antibody", Science 237 (1987), p. 1041-1043.
40. Bryant, R. A. R., Hansen, D. E., "Direct Measurement of the Uncatalyzed Rate of Hydrolysis of a Peptide Bond", J. Am. Chem. Soc. 118 (1996), p. 5498-5499
41. Wiberg, K. B. In, "The Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry, and Material Science", Greenberg, A., Breneman, C. M., Liebman, J. F., Eds.; John Wiley & Sons, Inc, New York 2000, p. 35-45
42. Stewart, J. D., Krebs, J. F., Siuzdak, G., Berdis, A. J., Smithrud, D. B., Benkovic, S. J., "Dissection of an Antibody-Catalyzed Reaction", Proc. Natl. Acad. Sci. USA 91 (1994), p. 7404-7409
43. Martin, M. T., Angeles, T. S., Sugasawara, R., Aman, N. I., Napper, A. D., Darsley, M. J., Sanchez, R. I., Booth, P., Titmas, R. C., "AntibodyCatalyzed Hydrolysis of an Unsubstituted Amide", J. Am. Chem. Soc. 116 (1994), p. 6508-6512
44. Gibbs, R. A., Taylor, S., Benkovic, S. J., "Antibody-catalyzed rearrangement of the peptide bond", Science 258 (1992), p. 803-805
45. Ersoy, O., Fleck, R., Sinskey, A., Masamune, S., "Antibody catalyzed cleavage of an amide bond using an external nucleophilic cofactor", J. Am. Chem. Soc. 120 (1998), p. 817-818
46. Dwek, R. A., Edge, C. J., Harvey, D. J., Wormald, M. R., Parekh, R. B., "Analysis of glycoprotein-associated oligosaccharides", Annu. Rev. Biochem. 62 (1993), p. 65-100
47. Reymond, J.-L., Janda, K. D., Lerner, R. A., "Antibody-catalyzed hydrolysis of glycosidic compounds", Angew. Chem. Int. Ed. Engl. 30 (1991), p. 1711-1713
48. Yu, J., Hsieh, L., Kochersperger, L., Yonkovich, S., Stephans, J. C., Gallop, M. A., Schultz, P. G., "On the path to antibody glycosidases", Angew. Chem. Int. Ed. Engl. 33 (1994), p. 339-341
49. Schramm, V. L., Horenstein, B. A., Kline, P. C., "Transition state analysis and inhibitor design for enzymatic reactions", J. Biol. Chem. 269 (1994), p. 18259-18262
50. Kuroki, R., Weaver, L. H., Matthews, B. W., "A covalent enzyme-substrate intermediate with saccharide distortion in a mutant T4 lysozyme", Science 262 (1993), p. 2030-2033
51. Suga, H., Tanimoto, N., Sinskey, A. J., Masamune, S., "Glycosidase Antibodies Induced to a Half-Chair Transition-State Analog", J. Am. Chem. Soc. 116 (1994), p. 11197-11198
52. Janda, K. D., Lo, L.-C., Lo, C.-H. L., Sim, M.-N., Wang, R., Wong, C.-H., Lerner, R. A., "Chemical selection for catalysis in combinatorial antibody libraries", Science 275 (1997), p. 945-948
53. Yu, J., Choi, S. Y., Moon, K-D., Chung, H. H., Youn, H.J., Jeong, H. J., Park, H., Schultz P. G., "A glycosidase antibody elicited against a chair-like transition state analog by in vitro immunization", Proc. Natl. Acad. Sci. USA 95 (1998), p. 2880-2884
54. Chin, J., "Developing artificial hydrolytic metalloenzymes by a unified mechanistic approach", Acc. Chem. Res 24 (1991), p. 145-152
55. Scanlan, T. S., Prudent, J. R., Schultz, P. G., "Antibody-catalyzed hydrolysis of phosphate monoesters", J. Am. Chem. Soc. 113 (1991), p. 9397-9398
56. Lavey, B. J., Janda, K. D., "Catalytic Antibody mediated Hydrolysis of Paraoxon", J. Org. Chem. 61 (1996), p. 7633-7636
57. Rosenblum, J. S., Lo, S.-C., Li, T., Janda, K. D., Lerner, R. A., "Antibodycatalyzed Phosphate Triester Hydrolysis", Angew. Chem. Int. Ed. Engl. 34 (1995), p. 2275-2277
58. Weiner, D. P., Wiemann, T., Wolfe, M. M., Wentworth, P. J., Janda, K. D., "A Pentacoordinate Oxorhenium (V) Metallochelate Elicits Antibody Catalysts for Phosphodiester Cleavage", J. Am. Chem. Soc. 117 (1997), p. 4088-4089
59. Abraham, L., Czerwonka, R., Hiersmann, M., "The Catalytic Enantioselective Claisen Rearrangement of an Allyl Vinyl Ether", Angew. Chem. Int. Ed. 40, (2001), p. 4700-4703
60. Yoon, T. P., MacMillan, D. W. C., " Enantioselective Claisen Rearrangements: Development of a First Generation Asymmetric Acyl-Claisen Reaction", J. Am. Chem. Soc. 123 (2001), p. 2911-2912
61. Bartlett, P. A., Nakagawa, Y., Johnson, C. R., Reich, S. H., Luis, A., "Chorismate Mutase Inhibitor: Synthesis and Evaluation of Some Potential Transition-State Analogs", J. Org. Chem. 53 (1988), p. 3195-3210
62. Jackson, D. Y., Jacobs, J. W., Sugasawara, R., Reich, S. H., Bartlett, P. A., Schultz, P. G., "An antibody-catalyzed Claisen rearrangement", J. Am. Chem. Soc. 110 (1988), p. 4841-4842
63. D. Y. Jackson, K. D., Liang, M. N., Bartlett, P. A., Schultz P. G., "Activation Parameters and Stereochemistry of an Antibody-Catalyzed Claisen Rearrangement", Angew. Chem. Int. Ed. Engl. 31 (1992), p. 182-183
64. Hilvert, D., Carpenter, S. H., Nared, K. D., Auditor, M.-T. M., "Catalysis of concerted reactions by antibody: the Claisen rearrangement", Proc. Natl. Acad. Sci. USA 85 (1988), p. 4953-4955.
65. Hilvert, D., Nared, K. D., "Stereospecific Claisen rearrangement catalyzed by an antibody", J. Am. Chem. Soc. 110 (1988), p. 5593-5594
66. Haynes, M. R., Stura, E. A., Hilvert, D., Wilson, I. A., "Routes to catalysis: structure of a catalytic antibody and comparison with its natural counterpart", Science 263 (1994), p. 646-652
67. Tang, Y., Hicks, J. B., Hilvert D., "In vivo catalysis of a metabolically essential reaction by an antibody", Proc. Natl. Acad. Sci. USA 88 (1991), p. 8784-8786
68. Braisted, A. C., Schultz, P. G., "An Antibody-Catalyzed Oxy-Cope Rearrangement", J. Am. Chem. Soc. 116 (1994), p. 2211-2212
69. Ulrich, H. D., Driggers, E. M., Schultz P. G., "Antibody catalysis of peri-cyclic reactions", Acta Chim. Scand. 50 (1996), p. 328-332
70. Ullrich, H. D., Mundorff, E., Santarsiero, B. D., Driggers, E. M., Stevens, R. C., Schultz, P. G., "The interplay between binding energy and catalysis in the evolution of a catalytic antibody", Nature 389 (1997), p. 271-275
71. Zhou, Z. S., Jiang, N., Hilvert, D., "An Antibody-Catalyzed Selenoxide Elimination", J. Am. Chem. Soc. 119 (1997), p. 3623-3624
72. Hlvert, D., Hill, K. W., Nared, K. D., Auditor M.-T. M., "Antibody catalysis of the Diels-Alder reaction", J. Am. Chem. Soc. 111 (1989), p. 9261-9262
73. Braisted, A. C., Schultz, P. G., "An Antibody-catalyzed bimolecular Diels-Alder reaction", J. Am. Chem. Soc. 112 (1990), p. 7430-7431
74. Gouverneur, V. E., Houk, K. N., de Pascual-Teresa, B., Beno, B., Janda, K. D., Lerner, R. A., "Control of the exo and endo Pathways of the Diels-alder Reaction by Antibody Catalysis", Science 262 (1993), p. 204-208
75. Yli-Kauhaluoma, J. T., Ashley, J. A., Lo, C.-H., Tucker, L., Wolfe, M. M., Janda, K. D., "Anti-Metallocene Antibodies: A New Approach to Enantioselective Catalysis of the Diels-Alder Reaction", J. Am. Chem. Soc. 117 (1995), p. 7041
76. Heine, A., Stura, E. A., YliKauhaluoma, J. T., Gao, C., Deng, Q., Beno, B. R., Houk, K. N., Janda, K. D., Wilson, I. A., "An antibody exo Diels-Alderase inhibitor complex at 1.95 angstrom resolution", Science 279 (1998), p. 1934
77. Meekel, A. A. P., Resmini, M., Pandit, U. K., "Regioselectivity and Enantioselectivity in an Antibody Catalyzed Hetero Diels-Alder Reaction", Bioorg. Med. Chem. 4(1996), p. 1051-1057
78. Meekel, A. A. P., Resmini, M., Pandit, U. K., "First example of an antibody-catalyzed hetero Diels-Alder reaction", J. Chem. Soc., Chem. Commun. 571 (1995)
79. Resmini, M., Meekel, A. A. P., Pandit, U. K., "Catalytic antibodies: regio- and enantioselectivity in a hetero Diels-Alder reaction", Pure Appl. Chem. 68 (1996), p. 2025-2028
80. Hu, Y.-J., Ji, Y.-Y., Wu, Y.-L., Yang, B. H., Yeh, M., "Polyclonal Catalytic Antibody for hetero-Cycloaddition of Hepta-1,3-diene with Ethyl Glyoxy-late An Approach to the Synthesis of 2-Nonulosonic Acid Analogs", Bioorg. Med. Chem. Lett 7(1997), p. 1601-1606
81. Shi, Z.-D., Yang, B.-H., Wu, Y-L., Pan, Y. J., Ji, Y. Y., Yeh, M., "First Example of an Antibody-Catalyzed Aza Diels-Alder Reaction", Bioorg. Med. Chem. Lett. 12 (2002), p. 2321-2324
82. Toker, J. D., Wentworth, P., Hu, Y., Houk, K. N., Janda, K. D., "AntibodyCatalysis of a Biomolecular Asymmetric 1,3-Dipolar Cycloaddition Reaction", J. Am. Chem. Soc. 122 (2000), p. 3244-3245
83. Machajewski, T. D., Wong, C-H., "The Catalytic Asymmetric Aldol Reaction", Angew. Chem. Int. Ed. 39 (2000), p. 1352-1374
84. Yamada, Y. M. A., Yoshikawa, N., Sasai, H., Shibasaki, M., "Direct catalytic asymmetric aldol reactions of aldehydes with unmodified ke-tones", Angew. Chem. Int. Ed. Engl. 36 (1997), p. 1871-1873
85. Koch, T., Reymond, J.-L., Lerner, R. A., "Antibody catalysis of multistep reactions: an aldol addition followed by a disfavoured elimination", J. Am. Chem. Soc. 117 (1995), p. 9383-9387
86. Reymond, J.-L., Chen, Y., "Catalytic, Enantioselective Aldol reaction with an Artificial Aldolase Assembled from a Primary Amine and an Antibody", J. Org. Chem. 60 (1995), p. 6970-6979
87. Reymond, J.-L., Angew. Chem. Int. Ed. 34 (1995), p. 2285-2287
88. Wagner, J., Lerner, R. A., Barbas III C. F., "Efficient aldolase catalytic antibodies that use the enamine mechanism of natural enzymes", Science 270 (1995), p. 1797-1800
89. Barbas III, C. F., Heine, A., Zhong, G., Hoffman, T., Gramatikova, S., Bjornestedt, R., List, B., Anderson, J., Stura, E. A., Wilson, I. A., Lerner, R. A., "Immune versus natural selection: antibody aldolases with enzymic rates but broader scope", Science 278 (1997), p. 2085
90. Hoffman, T., Zhong, G., List, B., Shabat, D., Anderson, J., Gramatikova, S., Lerner, R. A., Barbas III, C. F., "Aldolase Antibodies of Remarkable Scope", J. Am. Chem. Soc. 120 (1998), p. 2768-2779
91. Zhong, G., Hoffman, T., Lerner, R. A., Danishefsky, S., Barbas III, C. F., "Antibody-Catalyzed Enantioselective Robinson Annulation", J. Am. Chem. Soc. 119 (1997), p. 8131-8132
92. Chen, L., Dumas, D. P., Wong, C.-H., "Deoxyribose 5-phosphate aldolase as a catalyst in asymmetric aldol condensation", J. Am. Chem. Soc. 114 (1992), 741
93. Zhong, G., Shabat, D., List, B., Anderson, J., Sinha, S. C., Lerner, R. A., Barbas III, C. F., "Catalytic Enantioselective Retro-Aldol Reactions: Kinetic Resolution of â-Hydroxyketones with Aldolase Antibodies", Angew. Chem. Int. Ed. 37 (1998), p. 2481-2484
94. List, B., Shabat, D., Zhong, G., Turner, J. M., Li, A., Bui, T., Anderson, J., Lerner, R. A., Barbas III, C. F., "A Catalytic Enantioselective Route to Hydroxy-Substituted Quaternary Carbon Centers: Resolution of Tertiary Aldols with a Catalytic Antibody", J. Am. Chem. Soc. 121 (1999), p. 7283-7291
95. List, B., Lerner, R. A., Barbas III, C. F., "Enantioselective Aldol Cyclodehydrations Catalyzed by Antibody 38C2", Org. Lett. 1(1999), p. 59-61
96. Zhong, G., Lerner, R. A., Barbas III, C. F., "Broadening the Aldolase Catalytic Antibody Repertoire by Combining Reactive Immunization and Transition State Theory: New Enantio- and Diastereoselectivities", Angew. Chem. Int. Ed. 38 (1999), p. 3738-3741
97. Maggiotti, V., Resmini, M., Gouverneur, V., "Unprecedented Regiocontrol Using an Aldolase I Antibody", Angew. Chem. Int. Ed. 41 (2002), p. 1012-1014
98. Shulma, A., Sitry, D., Shulman, H., Keinan, E., "Highly Efficient Antibody-Catalyzed Deuteration of Carbonyl Compounds", Chem. Eur. J. 8(2002), p. 229-239
99. Flanagan, M. E., Jacobsen, J. R., Sweet, E., Schultz, P. G., "AntibodyCatalyzed Retro-Aldol Reaction", J. Am. Chem. Soc. 118 (1996), p. 6078-6079
100. Janda, K. D., Shevlin, C. G., Lerner, R. A., "Antibody catalysis of a disfavoured chemical transformation", Science 259 (1993), p. 490-493
101. Na, J., Houk, K. N., Shevlin, C. G., Janda, K. D., Lerner, R. A., "The Energetic Advantage of 5-Exo Versus 6-Endo Epoxide Openings: A Preference Overwhelmed by Antibody Catalysis", J. Am. Chem. Soc. 115 (1993), p. 8543
102. Shevlin, C. G., Hilton, S., Janda, K. D., "Automation of antibody catalysis: a practical methodology for the use of catalytic antibodies in organic synthesis", Bioorg. Med. Chem. Lett. 4(2) (1994), p. 297-302
103. Janda, K. D., Shevlin, C. G., Lerner, R. A., "Oxepane Synthesis Along a disfavored Pathway: The Rerouting of a Chemical Reaction Using a Catalytic Antibody", J. Am. Chem. Soc. 117 (1995), p. 2659-2660
104. Kitazume, T., Takeda M., "A cyclization reaction catalyzed by antibodies", J. Chem. Soc., Chem. Commun. (1995), p. 39-40
105. Abe, I., Rohmer, M., Prestwich, G. D., "Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes", Chem. Rev. 93 (1993), p. 2189-2206
106. Pale-Grosdemange, C., Feil, C., Rohmer, M., Poralla, K., "Occurrence of Cationic Intermediates and Deficient Control during the Enzymatic Cyclization of Squalene to Hopanoids", Angew. Chem. Int. Ed. 37 (1998), p. 2237-2240
107. Li, T., Janda, K. D., Ashley, J. A., Lerner, R. A., "Antibody catalyzed cationic cyclization", Science 264 (1994), 1289-1293
108. Li, T., Janda, K. D., Lerner, R. A., "Cationic cyclopropanation by antibody catalysis", Nature 379 (1996), p. 326-327
109. Li, S. Hilton, K. D. Janda, "Remarkable Ability of Different Antibody Catalysts To Control and Diversify the Product Outcome of Cationic Cyclization Reactions", J. Am. Chem. Soc. 117 (1995), p. 3308-3309
110. Hasserodt, J., Janda, K. D., Lerner, R. A., "Formation of Bridge-Methylated Decalins by Antibody-Catalyzed Tandem Cationic Cyclization", J. Am. Chem. Soc. 119 (1997), p. 5994-5998
111. Paschall, C. M., Hasserodt, J., Jones, T., Lerner, R. A., Janda, K. D., Christianson, D. W., "Convergence of Catalytic Antibody and Terpene Cyclase Mechanisms: Polyene Cyclization Directed by Carbocation-ð Interactions", Angew. Chem. Int. Ed. 38 (1999), p. 1743-1747
112. Hasserodt, J., Janda, J. D., Lerner, R. A., "Antibodies Mimic of Natural Oxidosqualene-Cyclase Action in Steroid Ring A Formation", J. Am. Chem. Soc. 122 (2000), p. 40-45
113. Jakoby, W. B., Ziegler, D. M., "The enzymes of detoxification", J. Biol. Chem. 265 (1990), p. 20715-20718
114. Holland, H. L., "Chiral sulfoxidation by biotransformation of organic sulfides", Chem. Rev. 88 (1988), p. 473-485
115. Kim, J. I., Nagano, T., Higuchi, T., Hirobe, M., Shimada, I., Arada, Y., "Conformation and stereoselective reduction of hapten side chains in the antibody combining site", J. Am. Chem. Soc. 113 (1991), p. 9392-9394
116. Nakayama, G. R., Schultz, P. G., "Stereospecific antibody-catalyzed reduction of an alpha-keto amide", J. Am. Chem. Soc. 114 (1992), p. 780-781
117. L. C. Hsieh, S. Yonkovich, L. Kochersperger, P. G. Schultz, "Controlling chemical reactivity with antibodies", Science 260 (1993), p. 337-339
118. Jacobsen, E. N., Finney, N. S., "Synthetic and biological catalysts in chemical synthesis: how to assess practical utility?", Chem. Biol. 1(1994), p. 85-90
119. Allain, E. J., Hager, L. P., Deng, L., Jacobsen, E. N., "Highly enantioselective epoxidation of disubstituted alkenes with hydrogen peroxide catalyzed by chloroperoxidase", J. Am. Chem. Soc. 115 (1993), p. 4415
120. Koch, A., Reymond, J.-L., Lerner, R. A., "Antibody-Catalyzed Activation of Unfunctionalized Olefins for Highly Enantioselective Asymmetric Epoxidation", J. Am. Chem. Soc. 116 (1994), p. 803-804
121. Chen, Y., Reymond, J.-L., "Enantios-elective epoxidation with a library of catalytic antibodies", Synthesis 6 (2001), p. 934-936
122. Hsieh, L. C., Stephans, J. C., Schultz, P. G., "An Efficient Antibody-Catalyzed Oxygenation Reaction", J. Am. Chem. Soc. 116 (1994), p. 2167-2168
123. Hsieh-Wilson, L. C., Schultz, P. G., Stevens, R. C., "Insights into antibody catalysis: Structure of an oxygenation catalyst at 1.9-A resolution", Proc. Natl. Acad. Sci. USA 93 (1996), p. 5363-5367
124. Eames, J., Weerasooriya N. "Recent advances into the enantioselective protonation of prostereogenic enol derivatives", Tetrahedron: Asymmetry 12 (2001), p. 1-24
125. Matsumoto, K., Tsutsumi, S., Ihori, T., Ohta, H., "Enzyme-mediated enantioface-differentiating hydrolysis of alpha-substituted cycloalkanone enol esters", J. Am. Chem. Soc. 112 (1990), p. 9614
126. Fujii, I., Lerner, R. A., Janda, K. D., "Enantiofacial protonation by catalytic antibodies", J. Am. Chem. Soc. 113 (1991), p. 8528-8529
127. Reymond, J-L., Janda, K. D., Lerner, R. A., "Highly Enantioselective Protonation Catalyzed by an Antibody", J. Am. Chem. Soc. 114 (1992), p. 2257-2258
128. Sinha, S. C., Keinan, E., "á-Multistriatin: the first total synthesis of a natural product via antibody catalysis", Isr. J. Chem. 36 (1996), p. 185-193
129. Sinha, S. C., Keinan, E., "Catalytic Antibodies in Organic Synthesis. Asymmetric Synthesis of (-)-á-Multistriatin", J. Am. Chem. Soc. 117 (1995), p. 3653-3654
130. Sinha, S. C., Keinan, E., Reymond, J.-L., "Antibody-catalyzed reversal of chemoselectivity", Proc. Natl. Acd. Sci. USA 90 (1993), p. 11910-11913
131. Shabat, D., Shulman, H., Itzhaky, H., Reymond, J-L., Keinan, "Enantioselectivity vs. kinetic resolution in antibody catalysis: formation of the (S) product despite preferential binding of the (R) intermediate", Chem. Commun. 8(1998), p. 1759-1760
132. Bartsch, R. A., Zavada, J., "Stereochemical and base species dichotomies in olefin-forming E2 eliminations", Chem. Rev. 80, (1980), p. 453-494
133. Cravatt, B. F., Ashley, J. A., Janda, K. D., Boger, D. L., Lerner, R. A., "Crossing Extreme Mechanistic Barriers by Antibody Catalysis: Syn Elimination to a Cis Olefin", J. Am. Chem. Soc. 116 (1994), p. 6013-6014
134. Briot, A., Bujard, M., Gouverneur, V., Mioskowski, C., "Design and Synthesis of Haptens for the Catalytic Antibody-Promoted Dynamic Kinetic Resolution of Oxazolin-5-ones", Eur. J. Org. Chem. (2002), p. 139-144
135. Vedejs, E., Chen, X., "Kinetic Resolution of Secondary Alcohols. Enantioseelctive Acylation Mediated by a Chiral (Dimethylamino)pyridine Derivative", J. Am. Chem. Soc. 118 (1996), p. 1809-1810
136. Wallace, J. S., Baldwin, B. W., Morrow, C. J., "Separation of remote diol and triol stereoisomers by enzyme-catalyzed esterification in organic media or hydrolysis in aqueous media", J. Org. Chem. 57 (1992), p. 5231-5239
137. Cook, C. E., Allen, D. A., Miller, D. B., Whisnant, C. C., "AntibodyCatalyzed Michael Reaction of Cyanide with an á, â-Unsaturated Ketone", J. Am. Chem. Soc. 117 (1995), p. 7269-7270
138. Sharpless, K. B., Verhoeven, T. R., "Metal-catalyzed highly selective oxygenations of olefins and acetylenes with tert-butyl hydroperoxide. Practical considerations and mechanisms", Aldrichimica Acta 12 (1979), 63-74
139. Hoveyda, A. H., Evans, D. A., Fu, G. C., "Substrate-directable chemical reactions", Chem. Rev. 93 (1993), p. 1307-1370
140. Johnson, R. A., Sharpless, K. B., In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCA, Weinheim 1993, p. 227-272
141. Takaya, H., Ohta, T., Noyori, R. ref 112, p. 1-39
142. Jacobsen, E. N., Zhang, W., Muci, A. R., Ecker, J. R., Deng, Li., "Highly enantioselective epoxidation catalysts derived from 1,2-aminocyclohexane", J. Am. Chem. Soc. 113 (1991), p. 7063
143. Sinha, S. C., Sun, J., Miller, G. P., Wartmann, M., Lerner, R. A., "Catalytic antibody route to the naturally occurring epothilones: total synthesis of epothilones A-F", Chem. Eur. J. 7(2001), p. 1691-1702
144. Sinha, S. C., Barbas III, C. F., Lerner, R. A., "The antibody catalysis route to the total synthesis of epothilones", Proc. Natl. Acad. Sci 25 (1998), p. 14603-14608
145. Sinha, S.C., Sun, J., Miller, G. P., Wartmann, M., Lerner, R. A., "Catalytic antibody route to the naturally occurring epothilones: total synthesis of epothilones A-F", Chemistry 7 (2001), p. 1691-1702
146. Sinha, S. C., Sun, J., Wartman, M., Lerner, R. A., "Synthesis of Epothilones Analogs by Antibody-Catalyzed Resolution of Thiazole Aldol Synthons on a Multi-gram Scale. Biological Consequences of C-13 Alkylation of Epothilones", ChemBioChem 2(2001), p. 656-665
147. List, B., Shabat, D., Barbas III, C. F., Lerner, R. A., "Enantioselective Total Synthesis of Some Brevicomins Using Aldolase Antibody 38C2", Chem. Eur. J. 4(1998), p. 881-885
148. Hilvert, D., "Critical analysis of Antibody Catalysis", Annu. Rev. Biochem. 69 (2000), p. 751-793