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R. Breslow, Centenary Lecture, Chern. Soc. , 1, 553 (1972). 2. R. L. van Etten, J. F. Sebastian, G. A. Clowes and M. C. Bender, J. Am. Chern. a. L Czarniecki and R. Breslow, J. Amer. Chern. , 100, 771 (1978); b. R. F. Czarniecki, J. Emert, and H. Hamaguchi, J. Amer. Chern. , 102, 762 (1980): c. G. Trainor, R. Breslow, J. Ame;-: Chern. , 103, 154 (1981); d. R. Breslow, G. Trainor, and A. Ueno, J. Am. Chern. , 105,2739 (1983). 4. J. Ie Noble, S. Srivastava, R. Breslow and G. Trainor, J. Am. Chern.
E. Overman, J. Amer. Chern. , 92, 1075 (1970). 6. g. B. Siegel, A. Pinter, and R. Breslow, J. Amer. Chern. , 99, 2309 (1977). 7. G. Trainor, unpublished work. 8. A. Ueno, R. , 23, 3451-3454 (1982). 9. R. W. Czarnik, J. Am. Chern. , 105, 1390 (1983). 10. K. Nakasuji. unpublished work. 11. D. J. Cram and H. E. Katz. J. Am. Chern. Soc •• lOS. 135 (1983). 12. D. Cram, International Symposium on Bioorganic Chemistry, New York, 1985. 13. D. Rideout, R. Breslow. J. Amer. Chern. , 102,7816 (1980). 14. R.
It seemed to us likely that we could achieve stereochemical control of the synthesis of amino acids during transamination if we could attach a proton transfer catalytic group to pyridoxamine, and if it would act not only to remove the proton from the CH group of pyridoxamine but also to put that proton on the new asymmetric carbon of the product amino acid. As we have described,(21) kinetic studies indicate that this mechanism operates provided we use a sufficiently long flexible base. With such a basic arm attached at C-5 of pyridoxamine we observe much faster transamination, and the dependence of the rate on the length of the basic arm indicates clearly that the base is acting to deliver the proton to the new carbon, not just remove it from the CH~ group.