Summary
1. An empirical method for the quantitative determination of the number of NH groups of different types in peptides based on measurements of the integral intensity of the amide A bands in the IR spectra has been developed.
2. The IR spectra of the diastereomeric cyclohexaalanyls in CHCl3 solutions have been studied; they indicate the participation of an average of four NH groups in IMBHs.
3. On the basis of a theoretical conformational analysis and of dipole-moment measurements, the system of IMHBs and the type of dominant conformation of the cyclohexapeptides in nonpolar solvents have been established.
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Literature cited
Yu. A. Ovchinnikov, V. T. Ivanov, V. V. Shilin, and G. A. Kogan, Molekul. Biol.,3, 600 (1969).
V. T. Ivanov, V. V. Shilin, Ya. Bernat, and Yu. A. Ovchinnikov, Zh. Obshch. Khim.,41, 2318 (1971).
V. T. Ivanov, G. A. Kogan, E. N. Meshcheryakova, V. V. Shilin, and Yu. A. Ovchinnikov, Khim. Prirodn. Soedin.,7, 309 (1971).
S. L. Portnova, T. A. Balashova, V. F. Bystrov, V. V. Shilin, Ya. Bernat, V. T. Ivanov, and Yu. A. Ovchinnikov, Khim. Prirodn. Soedin.,7, 323 (1971).
V. T. Ivanov, S. L. Portnova, T. A. Balashova, V. F. Bystrov, V. V. Shilin, Ya. Bernat, and Yu. A. Ovchinnikov, Khim. Prirodn. Soedin.,7, 339 (1971).
G. Hedestrand, Z. Phys. Chem.,B2, 428 (1929).
B. V. Ioffe, Refractometric Methods in Chemistry [in Russian] GNTI (1960).
Yu. N. Chirgadze, Infrared Spectra and the Structure of Polypeptides [in Russian], Moscow (1965).
T. Miyazawa, in: Polyamino Acids, Polypeptides, and Proteins (editor M. A. Stahnman), University of Wisconsin Press, Madison (1962), p. 201.
T. Miyazawa, in: Aspects of Protein Structure (editor G. N. Ramachandran), Academic Press, New York (1963), p. 257.
S. Mizushima, The Structure of Molecules and Internal Rotation, Academic Press, New York (1954).
S. Mizushima, T. Shimanouchi, M. Tsuboi, and T. Azakawa, J. Amer. Chem. Soc.,79, 5357 (1957).
M. Tsuboi, T. Shimanouchi, and S. Mizushima, J. Amer. Chem. Soc.,81, 1406 (1959).
J. E. Shields and S. T. McDowell, J. Amer. Chem. Soc.,89, 2499 (1967).
J. E. Shields, S. T. McDowell, J. Pavlos, and G. R. Gray, J. Amer. Chem. Soc.,90, 3549 (1968).
S. L. Portnova, V. F. Bystrov, V. I. Tsetlin, V. T. Ivanov, and Yu. A. Ovchinnikov, Zh. Obshch. Khim.,38, 428 (1968).
V. T. Ivanov, I. A. Laine, N. D. Abdullaev, L. B. Senyavina, E. M. Popov, Yu. A. Ovchinnikov, and M. M. Shemyakin, Biochem. Biophys. Res. Commun.,34, 803 (1960).
Yu. A. Ovchinnikov, V. T. Ivanov, V. F. Bystrov, A. I. Miroshnikov, E. N. Shepel, N. D. Abdullaev, E. S. Efremov, and L. B. Senyavina, Biochem. Biophys. Res. Commun.,39, 217 (1970).
M. Avignon and P. V. Huong, Biopolymers,9, 427 (1970).
M. Avignon, P. V. Huong, L. Lascombe, M. Marrand, and J. Heel, Biopolymers,8, 69 (1969).
E. M. Popov, G. M. Lipkind, S. F. Arkhipova, and V. G. Dashevskii, Molekulyarnaya Biologiya,2, 622 (1968).
G. Pimentel and O. MacClennan, The Hydrogen Bond, W. H. Freeman, San Francisco (1960).
N. D. Sokolov, The Hydrogen Bond [in Russian], Moscow (1964).
L. A. Dement'eva, A. V. Iogansen, and G. A. Kurkchi, Zh. Prikl. Spektrosk.,10, 625 (1969).
A. V. Iogansen, Dokl. Akad. Nauk SSSR,164, 610 (1965).
V. Iogansen, G. A. Kurkchi, and B. V. Rassadin, Zh. Prikl. Spektrosk.,11, 1054 (1969).
N. N. Khovratovich and N. A. Borisevich, in: Opt. i Spektrosk., Collection 3 on Molecular Spectroscopy [in Russian], Leningrad (1967), p. 123.
O. M. Boyarchuk and V. N. Nikitin, Dokl. Akad. Nauk SSSR,159, 397 (1964).
D. N. Shigorin, N. V. Mikhailova, and O. A. Klyueva, Zh. Fiz. Khim.,30, 1591 (1965).
I. V. Shablygin, D. N. Shigorin, and N. V. Mikhailova, Zh. Prikl. Spektrosk.,3, 56 (1965).
M. H. J. Taverne, Rec. Trav. Chim.,16, 31 (1897).
T. Hans et al., The Chemistry of Penicillin, Princeton University Press, Princeton, (1949), pp. 144, 177, 187.
R. B. Morin, B. J. G. Jackson, R. A. Mueller, E. R. Lavagnino, B. Scanlon, and S. L. Andrews, J. Amer. Chem. Soc.,85, 1896 (1963).
M. M. Shemyakin, Yu. A. Ovchinnikov, V. T. Ivanov, V. K. Antonov, E. I. Vinogradova, A. M. Shkrob, G. G. Melenkov, A. V. Evstratov, I. A. Laine, E. I. Melnik, and I. D. Ryabova, J. Membrane Biol.,1, 402 (1969).
D. A. Ramsay, J. Amer. Chem. Soc.,74, 72 (1952).
B. Wilson and A. J. Wells, J. Chem. Phys.,14, 578 (1946).
V. N. Smirnov, Vestn. Mosk. Univ.,1969, No. 1, 61.
J. T. Edsall, P. J. Flory, J. C. Kendrew, A. M. Liquori, G. Nemethy, G. N. Ramachandran, and H. A. Scheraga, Biopolymers,4, 121 (1956).
C. M. Venkatochalam, Biopolymers,6, 1425 (1968).
C. Ramachandran and K. P. Sarathy, Int. J. Protein Res.,1, 103 (1969).
G. M. Lipkind, S. F. Arkhipova, and E. M. Popov, Molekul. Biol.,4, 509 (1970).
G. M. Lipkind, Author's abstract of dissertation [in Russian], Moscow (1970).
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M. M. Shemyakin Institute of the Chemistry of Natural Compounds of the Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 347–357, May–June, 1971.
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Ivanov, V.T., Senyavina, L.B., Efremov, E.S. et al. A study of the conformational states of cyclopeptide systems. Chem Nat Compd 7, 325–332 (1971). https://doi.org/10.1007/BF00569007
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DOI: https://doi.org/10.1007/BF00569007