Conclusions
-
1.
The optimum conformations of 2,5-diketomorpholine, 2,5-diketopiperazine, the trans- and cis-forms of methyl acetate and N-methylacetamide were calculated by a search for the extremes of the potential energy with variation of many variables.
-
2.
A method was developed for the calculation of the conformations of the simplest depsipeptide and peptide rings.
-
3.
The role of the nonvalence, electrostatic, and valence interactions in the stabilization of the transform of methyl acetate and N-methylacetamide was discussed.
-
4.
A calculation of the conformations of diketomorpholine and diketopiperazine indicated that the molecules have a nonplanar structure with angles of openingθ correspondingly 143.2 and 153.2°; considering nonvalence interactions of the atoms, the barriers for these molecules were 1.50 and 0.35 kcal/mole, respectively.
-
5.
A consideration of the electrostatic energy of interaction of the atoms does not introduce any appreciable changes into the conformation and magnitude of the barriers of the simplest depsipeptide and peptide rings.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
E. M. Popov, G. M. Lipkind, S. F. Arkhipova, and V. G. Dashevskii, Molek. Biologiya,22, 622 (1968).
R. Huisgen and H. Walz, Chem. Ber.,89, 2616 (1956).
R. Huisgen and H. Ott, Tetrahedron,6, 253 (1959).
E. M. Popov, V. G. Dashevskii, G. M. Lipkind, and S. F. Arkhipova, Molekul. Bio.,2, 612 (1968).
R. J. Kurland and E. B. Wilson, J. Chem. Phys.,27, 585 (1957).
D. Poland and H. A. Scheraga, Biochemistry,6, 3791 (1967).
R. A. Scott and H. A. Scheraga, J. Chem. Phys.,45, 2091 (1966).
A. Mathieson, Tetrahedron Letters, 81 (1963).
J. F. McConnell, A. Mathieson, and B. P. Schoenborn, Tetrahedron Letters, 445 (1962); Acta Cryst.,17, 472 (1964).
C. Romers, E. W. M. Rutten, C. A. A. van Dreil, and W. W. Sanders, Acta Cryst.,22, 893 (1967).
B. K. Vainshtein, Zh. Fiz. Khim.,29, 327 (1955).
R. Degeilh and E. Marsh, Acta Cryst.,12, 1007 (1959).
J. M. O'Gorman, W. Shand, and V. Schomaker, J. Amer. Chem. Soc.,72, 4222 (1950).
R. F. Curl, J. Chem. Phys.,30, 1529 (1959).
J. D. Swallen and C. C. Costain, J. Chem. Phys.,31, 1562 (1959).
W. J. Tabor, J. Chem. Phys.,27, 974 (1957).
W. M. Slie and T. A. Litovitz, J. Chem. Phys.,39, 1538 (1963).
J. E. Piercy and S. V. Subrahmanyam, J. Chem. Phys.,42, 1475 (1965).
S. V. Subrahmanyam and J. E. Piercy, J. Acoust. Soc. Amer.,37, 340 (1965).
K. M. Burundukov and V. F. Yakovlev, Zh. Fiz. Khimii,42, 2149 (1968).
C. C. Costain and J. M. Dowling, J. Chem. Phys.,32, 138 (1960).
R. Huisgen, H. Brade, and I. Glogger, Chem. Ber.,90, 1437 (1957).
R. Moccia and H. W. Thompson, Spectrochim. Acta.,10, 240 (1957).
J. L. Katz and B. Post, Acta Cryst.,13, 624 (1960).
D. Shaw, D. W. Lepard, and H. L. Welsh, J. Chem. Phys.,42, 3736 (1965).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 33–40, January, 1971.
Rights and permissions
About this article
Cite this article
Popov, E.M., Pletnev, V.Z., Lipkind, G.M. et al. Theoretical investigation of the conformations of cyclic peptide and depsipeptide compounds. Russ Chem Bull 20, 27–32 (1971). https://doi.org/10.1007/BF00849312
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00849312