Abstract
A wide range of chemical transformations can be catalyzed by antibody molecules elicited with rationally designed transition state analogs. The development of catalytic antibodies consequently represents one of the most versatile and general strategies for creating new enzymes to emerge in the last several years. Recent advances in the production and characterization of these agents are reviewed.
This contribution originally appeared in the NATO ASI series volume entitled “Chemical Synthesis: Gnosis to Prognosis” (C. Chatgilialoglu and V. Snieckus, eds.), 1995.
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References
This contribution originally appeared in the NATO ASI series volume entitled “Chemical Synthesis: Gnosis to Prognosis” (C. Chatgilialoglu and V. Snieckus, eds.), 1995.
Pressman, D.; Grossberg, A. (1968) The Structrual Basis of Antibody Specificity, Benjamin, New York.
Nisonoff, A., Hopper, J., and Spring, S. (1975) The Antibody Molecule, Academic Press, New York.
Kabat, E.A. (1976) Structural Concepts in Immunology and Immunochemistry, Holt, Reinhart and Winston, New York.
Alt, F.W., Blackwell, T.K., and Yancopoulos, G.D. (1987) Development of the primary antibody repertoire, Science 238, 1079.
Rajewsky, K., Förster, I., and Cumang, A. (1987) Evolutionary and somatic selection of the antibody repertoire in the mouse, Science 238, 1088.
Lerner, R.A., Benkovic, S.J., and Schultz, P.G. (1991) At the crossroads of chemistry and immunology: Catalytic antibodies, Science 252, 659.
Davies, D.R., Padlan, E.A., and Sheriff, S. (1990) Antibody-antigen complexes, Ann. Rev. Biochem. 59, 439.
Wilson, I.A. and Stanfield, R.L. (1993) Antibody-antigen interactions, Current Opinion in Struct. Biol 3, 113.
Jencks, W.P. (1969) Catalysis in Chemistry and Enzymology; McGraw-Hill: New York, p. 288.
Pauling, L. (1948) Chemical achievement and hope for the future, Am. Sci. 36, 51.
Andrews, P.R., Smith, G.D., and Young, I.G. (1973) Transition-state stabilization and enzymic catalysis. Kinetic and molecular orbital studies of the rearrangement of chorismate to prephenate, Biochemistry 12, 3492.
Sogo, S.G., Widlanski, T.S., Hoare, J.H., Grimshaw, C.E., Berchtold, G.A., and Knowles, J.R. (1984) Stereochemistry of the rearrangement of chorismate to prephenate: Chorismate mutase involves a chair transition state, J Am. Chem. Soc. 106, 2701.
Andrews, P.R., Cain, E.N., Rizardo, E., and Smith, G.D. (1977) Rearrangement of chorismate to prephenate. Use of chorismate mutase inhibitors to define the transition state structure, Biochemistry 16, 4848.
Addadi, L., Jaffe, E.K., and Knowles, J.R. (1984) Secondary tritium isotope effects as probes of the enzymic and nonenzymic conversion of chorismate to prephenate, Biochemistry 22, 4494.
Copley, S.D. and Knowles, J.R. (1987) The conformational equilibrium of chorismate in solution: Implications for the mechanism of the nonenzymic and the enzyme-catalyzed rearrangement of chorismate to prephenate, J. Am. Chem. Soc. 109, 5008.
Severence, D.L. and Jorgensen, W.L. (1992) Effects of hydration on the Claisen rearrangement of allyl vinyl ether from computer simulations, J. Am. Chem. Soc. 114, 10966.
Westheimer, F.H. (1962) Mechanisms related to enzyme catalysis, Adv. Enzymol. 24, 441.
Görisch, J. (1978) On the mechanism of the chorismate mutase reaction, Biochemistry 17, 3700.
Bartlett, P.A., Nakagawa, Y., Johnson, C.R., Reich, S.H., and Luis, A. (1988) Chorismate mutase inhibitors: Synthesis and evaluation of some potential transition-state analogues, J. Org. Chem. 53, 3195.
Hilvert, D., Carpenter, S.H., Nared, K.D., and Auditor, M.-T.M. (1988) Catalysis of concerted reactions by antibodies: The Claisen rearrangement, Proc. Natl. Acad. Sci. USA 85, 4953.
Jackson, D.Y., Jacobs, J.W., Sugasawara, R., Reich, S.H., Bartlett, P.A., and Schultz, P.G. (1988) An antibody-catalyzed Claisen rearrangement, J. Am. Chenu Soc. 110, 4841.
Hilvert, D. and Nared, K.D. (1988) Stereospecific Claisen rearrangement catalyzed by an antibody, J. Am Chem. Soc. 110, 5593.
Jackson, D.Y., Liang, M.N., Bartlett, P.A. and Schultz, P.G. (1992) Activation parameters and stereochemistry of an antibody-catalyzed Claisen rearrangement, Angew. Chem Int. Ed. Engl. 31, 182.
Campbell, A.P., Tarasow, T.M., Massefski, W., Wright, P.E., and Hilvert, D. (1993) Binding of a high-energy substrate conformer in antibody catalysis, Proc. Natl. Acad Sci. USA 90, 8663.
Haynes, M.R., Stura, E.A., Hilvert, D., and Wilson, I.A. (1994) Routes to catalysis: Structure of a catalytic antibody and comparison with its natural counterpart, Science 263, 646.
Chook, Y.M., Ke, H., and Lipscomb, W.N. (1993) Crystal structures of the monofunctional chorismate mutase from Bacillus subtilis and its complex with a transition state analog, Proc. Natl. Acad. Sci. USA 90, 8600.
Dunitz, J. (1994) The entropie cost of bound water in crystals and biomolecules, Science 264, 670.
Garrard, L.J. and Zhukovsky, E.A. (1992) Antibody expression in bacteriophage systems: The future of monoclonal antibodies? Current Opinion in Biotechnology 3, 474.
Tang, Y., Hicks, J.B., and Hilvert, D. (1991) In vivo catalysis of a metabolically essential reaction by an antibody, Proc. Natl. Acad. Sci. USA 88, 8784.
Stewart, J.D., Liotta, L.J., and Benkovic, S.J. (1993) Reaction mechanisms displayed by catalytic antibodies, Acc. Chem Res. 26, 396.
Golinelli-Pimpaneau, B., Gigant, B., Bizebard, T., Navaza, J., Saludjian, P., Zemel, R., Tawfik, D.S., Eshhar, Z., Green, B.S., and Knossow, M. (1994) Crystal structure of a catalytic antibody Fab with esterase-like activity, Structure 2, 175.
Stewart, J.D., Roberts, V.A., Thomas, N.R., Getzoff, E.D., and Benkovic, S.J. (1994) Site-directed mutagenesis of a catalytic antibody: An arginine and a histidine residue play key roles, Biochemistry 33, 1994, and references therein.
Janda, K.D., Schloeder, D., Benkovic, S.J., and Lerner, R.A. (1988) Induction of an antibody that catalyzes the hydrolysis of an amide bond, Science 241, 1188.
Lewis, C., Krämer, T., Robinson, S., and Hilvert, D. (1991) Medium effects in antibody-catalyzed reactions, Science 253, 1019.
Kemp, D.S. and Paul, K.G. (1975) The physical organic chemistry of benzisoxazoles. III. The mechanism and the effects of solents on rates of decarboxylation of benzisoxazole-3-carboxylic acids, J. Am Chem. Soc. 97, 7305.
Tarasow, T.M., Lewis, C., and Hilvert, D. (1994). Investigation of medium effects in a family of decarboxylase antibodies. J. Am. Chem. Soc. 116, 7959.
Casey, M.L., Kemp, D.S., Paul, K.G., and Cox, D.D. (1973) The physical organic chemistry of benzisoxazoles. I. The mechanism of the base-catalyzed decomposition of benzisoxazoles, J. Org. Chem. 38, 2294.
Thorn, S. N., Daniels, R. G., Auditor, M.-T. M. and Hilvert, D. (1995). Large rate accelerations in antibody catalysis by strategic use of haptenic charge. Nature 373, 228.
Hilvert, D., Hill, K.W., Nared, K.D., and Auditor, M.-T.M. (1989) Antibody catalysis of a Diels-Alder reaction, J. Am. Chem. Soc. 111, 9261.
Braisted, A.C. and Schultz, P.G. (1990) An antibody-catalyzed bimolecular Diels-Alder reaction, J. Am. Chem. Soc. 112, 7430.
Gouverneur, V.E., Houk, K.N., Pascual-Teresa, B., Beno, B., Janda, K.D., and Lerner, R.A. (1993) Control of the exo and endo pathways of the Diels-Alder reaction by antibody catalysis. Science 262, 204.
Hilvert, D. (1993). Antibody catalysis of carbon-carbon bond formation and cleavage. Acc. Chem. Res. 26, 552.
Arevalo, J.H., Stura, E.A., Taussig, M.J., and Wilson, I.A. (1993) Three-dimensional structure of an anti-steroid Fab’ and progesterone-Fab’ complex, J. Mol. Biol. 231, 103.
MacBeath, G. and Hilvert, D. (1994) Monitoring catalytic activity by immunoassay: Implications for screening, J. Am. Chem. Soc. 116, 6101.
Cravatt, B.F., Ashley, J.A., Janda, K.D., Boger, D.L., and Lerner, R.A. (1994) Crossing extreme mechanistic barriers by antibody catalysis: Syn elimination to a cis olefin, J. Am. Chem. Soc. 116, 6013.
Li, T., Janda, K.D., Ashley, J.A., and Lerner, R.A. (1994) Antibody catalyzed cationic cyclization, Science 264, 1289.
Sinha, S.C., Keinan, E., and Reymond, J.-L. (1993) Antibody-catalyzed reversal of chemoselectivity, Proc. Natl. Acad. Sci. USA 90, 11910.
Hsieh, L.C., Yonkovich, S., Kochersperger, L., and Schultz P.G. (1993) Controlling chemical reactivity with antibodies, Science 260, 337.
Janda, K.D., Shevlin, C.G., and Lerner, R.A. (1993) Antibody catalysis of a disfavored chemical transformation, Science 259, 490.
Na, J., Houk, K.N., Shevlin, C.G., Janda, K.D., and Lerner, R.A. (1993) The energetic advantage of 5-exo versus 6-endo epoxide openings: A preference overwhelmed by antibody catalysis, J. Am. Chenu. Soc. 115, 8453.
Reymond, J.-L., Reber, J.-L., and Lerner, R.A. (1994) Enantioselective, multigram-scale synthesis with a catalytic antibody, Angew. Chem. Int. Ed. Engl. 33, 475.
Tramontano, A., Janda, K.D., and Lerner, R.A. (1986) Catalytic antibodies, Science 234, 1566.
Pollack, S.J., Jacobs, J.W., and Schultz, P.G. (1986) Selective chemical catalysis by an antibody, Science 234, 1570.
Iverson, B.L. and Lerner, R.A. (1989) Sequence-specific peptide cleavage catalyzed by an antibody, Science 243, 1184.
Tawfik, D.S., Green, B.S., Chap, R., Sela, M., and Eshhar, Z. (1993) catELISA: A facile general route to catalytic antibodies, Proc. Natl. Acad. Sci. USA 90, 373.
Lesley, S.A., Patten, P.A., and Schultz, P.G. (1993) A genetic approach to the generation of antibodies with enhanced catalytic activities. Proc. Natl. Acad. Sci. USA 90, 1160.
Fischer, E. (1894) Einfluss der Configuration auf die Wirkung der Enzyme, Ber. Dt. Chem. Ges. 27, 2985.
Eschenmoser, A. (1994) One hundred years lock-and-key principle. Angew. Chem. Int. Ed. Engl. 33, 2363.
Lichtenthaler, F.W. (1994) 100 Years “Schlüssel-Schloss-Prinzip”: What made Emil Fischer use this analogy? Angew. Chem. Int. Ed. Engl. 33, 2364.
Koshland, D.E., Jr. (1994) The Key-Lock Theory and the Induced Fit Theory. Angew. Chem. Int. Ed. Engl. 33, 2375.
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Hilvert, D. (1995). Principles of Antibody Catalysis. In: Siegel, J.S. (eds) Supramolecular Stereochemistry. NATO ASI Series, vol 473. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-0353-4_10
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DOI: https://doi.org/10.1007/978-94-011-0353-4_10
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