Summary
1. All the conformational states of the methylamide of N-acetyl-L-histidine have been calculated.
2. It has been shown that in the case of the tautomer of the imidazole ring with a hydrogen atom on the\({\text{N}}^{\varepsilon _2 }\) atom, form R of the main chain is preferred, and in the tautomer with the proton on\({\text{N}}^\delta _1\) and also in the protonated state of the side chain B forms are preferred.
3. The conformational equilibrium is displaced in the direction of form I.
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Literature cited
E. M. Popov and G. M. Lipkind, Molekul. Biol.,5, 624 (1971).
G. M. Lipkind and E. M. Popov, Molekul. Biol.,5, 667 (1971).
E. M. Popov, G. M. Lipkind, S. F. Arkhipova, and V. G. Dashevskii, Molekul. Biol.,2, 612 (1968).
G. M. Lipkind, S. F. Arkhipova, and E. M. Popov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 315 (1970).
M. A. Kreissler, G. M. Lipkind, S. F. Arkhipova, and E. M. Popov, J. Chim. Phys., 913 (1974).
G. M. Lipkind and E. M. Popov, Int. J. Peptide Protein Res.,5, 371 (1973).
G. M. Lipkind, S. F. Arkhipova, and E. M. Popov, Int. J. Peptide Protein Res.,5, 381 (1973).
C. Long, Biochemists' Handbook, London (1961).
Biochim. Biophys. Acta,229, 1 (1971).
L. Pauling, The Nature of the Chemical Bond, third ed., Cornell Univ. Press, New York (1960).
M. S. Lehman, T. F. Koetzle, and W. C. Hamilton, Int. J. Peptide Protein Res.,4, 229 (1972).
J. Donohue and A. Caron, Acta Cryst.,17, 1178 (1964).
E. M. Popov, V. G. Dashevskii, G. M. Lipkind, and S. F. Arkhipova, Molekul. Biol.,2, 612 (1968).
D. Poland and H. A. Scheraga, Biochem.,6, 3791 (1967).
G. M. Lipkind, S. F. Arkhipova, and E. M. Popov, Zh. Strukt. Khim.,11, 121 (1970).
I. A. Shellmann, Compt. Rend. Trav. Lab. Carlsberg, Ser. Chim.,29, 223 (1955).
G. Pimentel and O. McClellan, The Hydrogen Bond, W. H. Freeman, San Francisco (1960).
R. A. Scott and H. A. Scheraga, J. Chem. Phys.,45, 2091 (1966).
H. A. Scheraga, Adv. Phys. Org. Chem.,6, 103 (1968).
P. N. Lewis, F. A. Momany, and H. A. Scheraga, Israel J. Chemistry,11, 121 (1973).
H. C. Watson, Progr. Stereochemistry,4, 299 (1969).
J. J. Birktoft and D. M. Blow, J. Mol. Biol.,68, 187 (1972).
F. A. Quiocho and W. N. Lipscomb, Advan. Protein Chem.,25, 1 (1971).
H. W. Wyckoff, D. Tsernoglou, A. W. Hanson, J. R. Kuox, B. Lee, and F. M. Richard, J. Biol. Chem.,245, 305 (1970).
Additional information
M. M. Shemyakin Institute of Biochemistry, Academy of Sciences of the USSR, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 371–378, May–June, 1976.
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Berlin, P., Kreisler, M., Arkhipova, S.F. et al. An investigation of the conformational states of the methylamide of N-acetyl-L-histidine. Chem Nat Compd 12, 323–328 (1976). https://doi.org/10.1007/BF00567808
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DOI: https://doi.org/10.1007/BF00567808