Conclusions
-
1.
We have synthesized chiral Ni(II) complexes containing a Schiff base of dehydroalanine with (S)-o-(N-benzylprolyl)aminoacetophenone and (S)-o-(N-benzylprolyl)aminobenzophenone.
-
2.
Addition of thiophenol and benzylmercaptan to the double bond of dehydroalanine in these complexes with subsequent separation of the diastereomeric complexes of S-phenylcysteine and S-benzylcysteine formed gives optically pure L-S-phenylcysteine and L-S-benzylcysteine.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
A. E. Braunstein, The Enzymes, Vol. 9 (3rd ed.), P. D. Boyer (ed.), Academic Press, New York (1973), pp. 379–481.
L. Davis and D. E. Metzler, The Enzymes, Vol. 7 (3rd ed.), P. D. Boyer (ed.), Academic Press, New York (1972), pp. 33–74.
U. Schmidt and E. Oler, Angew. Chem. Int. Ed. Engl., 15 (1976).
K. Sano and O. I. Sii, J. Chem. Appl. Microbiol.,16, 94 (1971).
S. Ikeeda, I. Fujita, and J. Hirose, Agr. Biol. Chem.,40, 517 (1976).
M. R. Bovarnik, J. Biol. Chem.,148, 151 (1943).
J. H. Brewster and C. J. Ciotti, J. Am. Chem. Soc.,7, 6214 (1955).
Yu. N. Belokon', A. G. Bulychev, S. V. Vitt, et al., J. Am. Chem. Soc.,107, 4552 (1985).
Yu. N. Belokon', A. S. Sagiyan, I. V. Ponomarenko, et al., J. Chem. Soc., Perkin Trans.2, 21 (1985).
Yu. N. Belokon', V. I. Maleyev, S. V. Vitt, et al., J. Chem. Soc Dalton Trans., 17 (1985).
J. P. Greenstein, S. M. Birnbaum, and M. C. Otey, J. Biol. Chem.,204, 307 (1953).
M. Walter and L. Ramaley, Anal. Chem.,45, 165 (1973).
A. Gordon and R. Ford, A Chemist's Companion: A Handbook of Practical Data, Techniques, and References, Wiley, New York (1973).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1618–1624, July, 1988.
Rights and permissions
About this article
Cite this article
Belokon', Y.N., Dzhamgaryan, S.M., Sagiyan, A.S. et al. Asymmetric biomimetic synthesis of S-substituted L- and D-cysteines via chiral Ni(II) complexes of dehydroalanine. Russ Chem Bull 37, 1434–1440 (1988). https://doi.org/10.1007/BF00962757
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00962757