Abstract
The importance and diversity of the biological functions of cyclopeptides and the new possibilities for investigating this extensive class of peculiar and often intricately built natural compounds have made them an alluring object of ever-increasing study. Interest is at present centering on their stereo-chemical features, which is not surprising in view of the importance of spatial structure to the biological properties of peptides and proteins: the conformation-activity relations are the key to their mode of action. The limited conformational flexibility of the cyclopeptides, usually resulting in the existence of a relatively small number of well-defined preferential conformations, facilitates their theoretical and physicochemical conformational analysis in solution.
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References
Abbott, N. B., and Ambrose, E. J., 1953, The conformation of the polypeptide chain in small peptides such as gramicidin S, Proc. Roy. Soc. 219A: 17.
Brewster, A. I., and Bovey, F. A., 1971, Conformation of cyclolinopeptide A observed by nuclear resonance spectroscopy, Proc. Natl. Acad. Sci. 68: 1199.
Bystrov, V. F., 1972, Spin–Spin interaction between geminai and vicinal protons, Uspekhi Khimii (Chem. Rev, Russian). 41: 512.
Bystrov, V. F., Portnova, S. L., Tsetlin, V. I., Ivanov, V. T., and Ovchinnikov, Yu. A., 1969, Conformational studies of peptide systems. The rotational states of the NH—CH fragment of alanine dipeptides by nuclear magnetic resonance, Tetrahedron 25: 493.
Bystrov, V. F., Ivanov, V. T., Koz’min, S. A., Mikhaleva, I. I., Khalilulina, K. Kh., Ovchinnikov, Yu. A., Fedin, E. I., and Petrovskii, P. V., 1972, Biologically active alkali metal complexones. A 13C-NMR study of ion–dipole interaction, FEBS Letters 21: 34.
Cary, L. W., Takita, T., and Ohnishi, M., 1971, A study of the secondary structure of ilamycin B1 by 300 MHz proton magnetic resonance, FEBS Letters 17: 145.
Dale, J., 1963, Macrocyclic compounds. III. Conformations of cycloalkanes and other flexible macrocycles, J. Chem. Soc. 1963: 93.
Dobler, M., Dunitz, J. D., and Krajewski, F., 1969, Structure of the K+ complex with eniatin B, a macrocyclic antibiotic with K+-transport properties, J. Mol. Biol. 42: 603.
Efremov, E. S., Senyavina, L. B., Zheltova, V. N., Ivanova, A. G., Kostetsky, P. V., Ivanov, V. T., Popov, E. M., and Ovchinnikov, Yu. A., 1973, Conformational states of N-acetyl a-amino acids methylamides and their N-methylated derivatives. I. Infra-red spectra, Khim. Prir. Soed. (Chem. Nat. Prod., Russian) 1973: 322.
Faulstich, H., Burgermeister, W., and Wieland, Th., 1972, Antamanide. Evidence for a conformational change and nonplanar amide groups, Biochem. Biophys. Res. Commun. 47: 975.
Feeney, J., Roberts, G. C. K., Rockey, J. H., and Burgen, A. S. V., 1971, Conformational studies of oxytocin and lysine vasopressin in aqueous solution using high resolution NMR spectroscopy, Nature New Biol. 232: 108.
Grell, E., Eggers. F., and Funck, T., 1971a, Dynamic properties and membrane activity of ion specific antibiotics, in “Abstracts, Symposium on Molecular Mechanisms of Antibiotic Action on Protein Biosynthesis and Membranes, University of Granada, Spain (June 1–4.1971),” p. 69.
Grell. E., Eggers, F., and Funck, T., 1971b, Konformationsanalyse und Kinetik der Konformationsänderungen von Cyclodepsipeptid-Antibiotika, Angew. Chem. 83: 903.
Hodgkin, D. C., and Oughton, B. M., 1957, Possible molecular models for gramicidin S and their relationship to present ideas of protein structure, Biochim. J. 65: 752.
Hunter, F., and Schwarz, L., 1967, Tyrocidines and gramicidin S (J1, J2), in, Tyrocidines and gramicidin S (J1, J2), in “Antibiotics,” Vol. 1: “Mechanism of Action” (D. Gottlieb and P. D. Shaw, eds.), p. 599, Printing House “Mir,” Moscow. 1969.
Ivanov, V. T., Laine, I. A., Abdullaev, N. D., Senyavina, L. B., Popov, E. M., Ovchinnikov, Yu. A., and Shemyakin, M. M., 1969, The physicochemical basis of the functioning of biological membranes. The conformation of valinomycin and its K+ complex in solution, Biochem. Biophys. Res. Commun. 34: 803.
Ivanov, V. T., Shilin, V. V., and Ovchinnikov, Yu. A., 1970, Synthesis of cyclic hexapeptides containing L(o)-alanine and glycine residues. Zhurn. Obshch. Khim. (J. Gen. Chem., Russian) 40:924
Ivanov, V. T., Kogan, G. A., Meshcheryakova, E. A., Shilin, V. V., and Ovchinnikov, Yu. A. 1971a, Conformational states of cyclopeptide systems. III. Cyclohexapeptides as a system of interacting amide chromophores, Khim. Prir. Soed. (Chem. Nat. Prod., Russian) 1972: 309.
Ivanov, V. T., Laine, I. A., Abdullaev, N. D., Pletnev, V. Z., Lipkind, G. M., Arkhipova, S. F., Senyavina, L. B., Meshcheryakova, E. N., Popov, E. M., Bystrov, V. F., and Ovchinnikov, Yu. A., 1971b, Conformational states of valinomycin and its complexes with alkaline cations in solution, Khim. Prir. Soed. (Chem. Nat. Prod., Russian) 1971: 221.
Ivanov, V. T., Miroshnikov, A. I., Abdullaev, N. D., Senyavina, L. B., Arkhipova, S. F., Uvarova, N. N., Khalilulina, K. Kh., Bystrov, V. F., and Ovchinnikov, Yu. A., 1971c, Conformation of the Na complex of antamanide in solution, Biochem. Biophys. Res. Commun. 42: 654.
Ivanov, V. T., Portnova, S. L., Balashova, T. A., Bystrov, V. F., Shilin, V. V., Biernat, J., and Ovchinnikov, Yu. A., 1971d, Conformational studies of cyclopeptide systems. V. NMR spectra of cyclohexapeptides built up of alanine and glycine residues. Spin–spin coupling constants of the NH—CH protons and the “pleated sheet” structure, Khim. Prir. Soed. (Chem. Nat. Prod.. Russian) 1971: 339.
Ivanov, V. T., Senyavina, L. B., Efremov, E. S., Shilin, V. V., and Ovchinnikov, Yu. A., 1971e, Conformational studies of cyclopeptide systems. VI. Infrared spectra and dipole moments of diastereomeric cyclohexaalanyls. Khim. Prir. Soed. (Chem. Nat. Prod., Russian) 1971: 347.
Ivanov, V. T., Shilin, V. V., Biernat, J.. and Ovchinnikov, Yu. A., 1971f, Conformational studies of cyclopeptide systems. 11. Synthesis of cyclic hexapeptides containing 1.(D)-alanine and glycine residues. Zh. Obshch. Khim. (J. Gen. Chem., Russian) 41: 2318.
Ivanov, V. T., Shilin, V. V., Kogan, G. A., Meshcheryakova, E. N., Senyavina, L. B., Efremov, E. S., and Ovchinnikov, Yu. A., 1971g, Circular dichroism, infrared spectra and dipole moments of diastereomeric cyclohexaalanyls, Tetrahedron Letters 1971: 2841.
Ivanov, V. T., Evstratov, A. V., Mikhaleva, I. I., Abdullaev, N. D., Bystrov, V. F., and Ovchinnikov, Yu. A., 1973, Conformation of enniatin B in non-polar solvents, Khim. Prir. Soed. (Chem. Nat. Prod. Russian) (in press).
Ivanov, V. T., Microshnikov. A. I., Kozmin, S. A., Uvarova, N. N., Khalilulina, K. Kh., Bystrov, V. F., and Ovchinnikov, Yu. A., 1973a, Conformational states of antamanide and its analogs in solution, Khim. Prir. Soed. (Chem. Nat. Prod., Russian) 1973: 378.
Ivanov, V. T., Miroshnikov, A. I., Snezhkova, E. G., Ovchinnikov, Yu. A., Kulikov, A., and Lichtenstein, H. I., 1973h, Electron paramagnetic resonance spectroscopy in the conformational studies of peptides. Gramicidin S, Khim. Prir. Soed. (Chem. Nat. Prod., Russian) 1973: 91.
Johnson, L. F., Schwartz, I. L., and Walter, R., 1969, Oxytocin and neurohypophyseal peptides: Spectral assignment and conformational analysis by 220 Mc nuclear resonance, Proc. Natl. Acad. Sci. 64: 1269.
Karle, I. L., and Karle, J., 1963, An application of a new phase determination procedure to the structure of cyclo(hexaglycyl) hemihydrate, Acta Crystallogr. 16: 969.
Karle, I. L., Gibson, J. W., and Karle, J., 1970, The conformation and crystal structure of the cyclic polypeptide rGly-Gly-n-Ala-Gly-Gly1.3H2O, J. Am. Chem. Soc. 92: 3755.
Kendrew, J. C., Klyne, W., Lifson, S., Miyazawa, T., Némethy, G., Phillips, D. C., Ramachandran, G. N., and Scheraga, H. A., 1970, Abbreviations and symbols for the description of the conformation of polypeptide chains, J. Mol. Biol. 52:1; Biochemistry 9: 3471.
Konnert, J., and Karle, I. L., 1969, The conformation and crystal structure of the cyclotetradepsipeptide D-Hyly-L-Melleu-D-HyIv-L-McVal-, J. Am. Chem. Soc. 91: 4888.
Kopple, K. D., 1971, Conformations of cyclic peptides. V. A proton magnetic resonance study of evolidine, cyclo-Ser-Phe-Leu-Pro-Val-Asn-Leu, Biopolymers 10: 1139.
Liquori, A. M., and Conti, F., 1968, NMR studies of gramicidin S in solution, Nature 217: 635.
Liquori, A. M., de Santis, P., Kovacs, A. L., and Mazzarella, L., 1966, Stereochemical code of amino acid residues: The molecular conformation of gramicidine, S, Nature 211: 1039.
Llinas, M., Klein, M. P., and Neilands, J. B., 1970, Solution conformation of ferrichrome, a microbial iron transport cyclohexapeptide, as deduced by high resolution proton magnetic resonance, J. Mol. Biol. 52: 399.
Ludescher, U., and Schwyzer, R., 1971, On the chirality of the cystine disulfide group: Assignment of helical sense in a model compound with a dihedral angle greater than ninety degrees using NMR and CD, Hely. Chim. Acta 54: 1637.
Miroshnikov, A. I.. Khalilulina, K. Kh. Uvarova, N. N., Ivanov, V. T., and Ovchinnikov, Yu. A., 1973, Synthesis and properties of the symmetric analogs of antamanide. Khim. Prir. Soed. (Chem. Nat. Prod., Russian) 1973: 214.
Momany, F. A., Vanderkooi, G., Tuttle, R. W., and Scheraga, H. A., 1969, Minimization of polypeptide energy. IV. Further studies of gramicidin S, Biochemistry 8: 744.
Ohnishi, M., and Urry, D. W., 1969, Temperature dependence of amide proton chemical shifts: The secondary structures of gramicidin S and valinomycin, Biochem. Biophys. Res. Commun. 36: 194.
Ohnishi, M., Fedarco, M. C., Baldeschwieler, J. D., and Johnson, L. F., 1972, Fourier transform C-13 NMR analysis of some free and potassium-ion complexed antibiotics, Biochem. Biophys. Res. Commun. 46: 312.
Ovchinnikov, Yu. A., Ivanov, V. T., Evstratov, A. V., Bystrov, V. F., Abdullaev, N. D., Popov, E. M., Lipkind, G. M., Arkhipova, S. F., Efremov, E. S., and Shemyakin, M. M., 1969, The physicochemical basis of the functioning of biological membranes: Dynamic conformational properties of enniatin B and its K+ complex in solution, Biochem. Biophys. Res. Commun. 37: 668.
Ovchinnikov, Yu. A., Ivanov, V. T., Bystrov, V. F., Miroshnikov, A. I., Shepel, E. N., Abdullaev, N. D., Efremov, E. S., and Senyavina, L. B., 1970, The conformation of gramicidin S and its N,N’-diacetylderivative in solutions, Biochem. Biophys. Res. Commun. 39: 217.
Ovchinnikov, Yu. A., Ivanov, V. T., and Shkrob, A. M., 1971, The chemistry and membrane activity of peptide ionophores, in “Proceedings of the International Symposium on Molecular Mechanisms of Antibiotic Action on Protein Biosynthesis and Membranes, June 1–4, 1971, Granada” (D. Vazquez, ed.), Elsevier, Amsterdam, 1972.
Pinkerton, M., Steinrauf, L. L., and Dawkins, P. L., 1969, The molecular structure and some transport properties of valinomycin, Biochem. Biophys. Res. Commun. 35: 512.
Popov, E. M., Lipkind, G. M.. and Arkhipova, S. F., 1970a, Theoretical conformational analysis of cyclotetraglycyl, in “Conformational Calculations of Complex Molecules” (A. I. Kitaigorodski and L. T. Perelman, eds.), pp. 120–127, Institute of Heat and Mass Exchange Press, Minsk.
Popov, E. M., Pletnev, V. Z., Evstratov, A. V., Ivanov, V. T., and Ovchinnikov, Yu. A., 1970b, Theoretical conformational analysis of cyclic hexadepsipeptides. Enniatins, Khim. Prir. Soed. (Chem. Nat. Prod., Russian) 1970: 616.
Portnova, S. L., Balashova, T. A., Bystrov, V. F., Shilin, V. V., Biernat, J., Ivanov, V. T., and Ovchinnikov, Yu. A., 1971a, Conformational studies of cyclopeptide systems. IV. NMR spectra of cyclohexapeptides built up of alanine and glycine residues: Chemical shifts and intramolecular hydrogen bonding, Khim. Prir. Soed. (Chem. Nat. Prod., Russian) 1971: 323.
Portnova, S. L., Shilin, V. V, Balashova, T. A., Biernat, J., Bystrov, V. F., Ivanov, V. T., and Ovchinnikov, Yu. A., 1971b, Conformational studies of cyclic peptides in solution. NMR spectra of cyclohexapeptides consisting of L(D)-alanine and glycine residues, Tetrahedron Letters 1971: 3085.
Ramakrishnan, C., and Sarathy, K. P., 1968, Stereochemical studies on cyclic peptides. III. Conformational analysis of cyclotetrapeptides, Biochim. Biophys. Acta 168: 402.
Ramakrishnan, C., and Sarathy, K. P., 1969, Stereochemical studies on cyclic peptides. V. Conformational analysis of cyclohexapeptides, Internat. J. Protein Res. 1: 103.
Sarathy, K. P., and Ramakrishnan, C., 1972, Stereochemical studies on cyclic peptides. VII. Effect of different types of energies on the hydrogen-bonded conformations of cyclic hexapeptides, Internat. J. Protein Res. 4: 1.
Scheraga, H. A., Leach, S. J., Scott. R. A., and Nemethy, G., 1965, Intramolecular forces and protein conformation, Disc. Faraday Soc. 40: 268.
Schmidt, G. M., Hodgkin, D. C., and Oughton, B. M., 1957, A crystallographic study of some derivatives of gramicidin S, Biochem. J. 65: 744.
Schwyzer, R., 1959, Synthetic routes to natural polypeptides, Rec. Chem. Progr. 20: 146.
Schwyzer, R., and Ludescher. U., 1968, Conformational study of gramicidin S using the phthalimide group as nuclear magnetic resonance marker, Biochemistry 7: 2519.
Schwyzer, R., and Ludescher, U., 1969, Untersuchungen über die Konformation des cyclischen Hexapeptides cyclo-Glycyl-L-proplyl-glycyl-glycyl-L-prolyl-glycyl mittels protonenmagnetischer Resonanz und Parallelen zum Cyclodecapeptid Gramicidin S, Heir. Chim. Acta 52: 2033.
Schwyzer, R., Sieber, P., and Gorup, B., 1958, Synthese for Polypeptide-Wirkstoffen, Chimia 12: 90.
Schwyzer, R., Carrion, J. P., Gorup, B., Notting, H., and Tun-Kyi, A., 1964, Verdoppelungserscheinungen beim Ringschluss von Peptiden. V. Relative Bedeutung der sterischen Hinderung und der Assoziation über Wasserstoff-Brücken bei Tripeptiden. Spectroscopische Versuche zur Konformationbestimmung, Heir. Chim. Acta 47: 441.
Scott, R. A., Vanderkooi, G.. Tuttle, R. W., Shames, P. M., and Scheraga, H. A., 1967, Minimization of polypeptide energy. III. Application of a rapid minimization technique to the calculation of preliminary structures of gramicidin S, Proc. Natl. Acad. Sci. 58: 2204.
Shemyakin, M. M., Ovchinnikov, Yu. A., Ivanov, V. T., Antonov, V. K., Vinogradova, E. I., Shkrob, A. M., Malenkov, G. M., Evstratov, A. V., Laine, I. A., Melnik, E. I., and Ryabova, I. D., 1969, Cyclodepsipeptides as chemical tools for studying ionic transport through membranes, J. Membrane Biol. 1: 402.
Shemyakin, M. M., Ovchinnikov, Yu. A., Ivanov, V. T., Evstratov, A. V., Mikhaleva, I. I., and Ryabova, I. D., 1973, Synthesis and antimicrobial activity of the analogs of enniatin antibiotics, Zhurn. Obshch. Khim. (J. Gen. Chem. Russian) (in press).
Sobell, H. M., Jain, S. C., Sakore, T. D., and Nordman, C. E., 1971, Stereochemistry of actinomycin—DNA binding, Nature New Biol. 231: 200.
Stern, A., Gibbons, W. A., and Craig, L. C., 1968, Conformational analysis of gramicidin S-A by nuclear magnetic resonance, Proc. Natl. Acad. Sci. 61: 734.
Tonelli, A., Patel, D. J., Goodman, M., Naider, F., Faulstich, H., and Wieland, Th., 1971, Experimental and calculated conformational characteristics of the cyclic decapeptide antamanide, Biochemistry 10: 3211.
Urry, D. W., 1970, “Spectroscopic Approaches to Biomolecular Conformation,” p. 263, American Medical Association, Chicago.
Urry, D. W., and Walter, W., 1971, Proposed conformation of oxytocin in solution, Proc. Natl. Acad. Sci. 68: 956.
Urry, D. W., Quadrifoglio, F., Walter, R., and Schwarz, I. L., 1968, Conformational studies on the neurohypophyseal hormones. The disulfide bridge of oxytocin, Proc. Natl. Acad. Sci. 60: 967.
Urry, D. W., Ohnishi, M., and Walter, R., 1970, Secondary structure of the peptide hormone oxytocine and its deamino analog, Proc. Natl. Acad. Sci 66: 111.
van Dreele, P. H., Brewster, A. I., Scheraga, H. A., Ferger, M. F., and du Vigneaud, V., 1971, Nuclear magnetic resonance spectrum of Lys-vasopressin and its structural implications, Proc. Natl. Acad. Sci. 68: 1028.
Vanderkooi, G., Leach, S. J., Némethy, G., Scott, R. A., and Scheraga, H. A., 1966, Initial attempts at a theoretical calculation of the conformation of gramicidin S, Biochemistry 5: 2991.
Walter, R., Gordon, W., Schwarz, I. L., Quadrifoglio, F., and Urry, D. W., 1968, Conformation studies on the neurohypophyseal oxytocin and its analogs, in “Peptides-1968: Proceedings of the Ninth European Peptide Symposium” (E. Bricas, ed.), p. 50, North-Holland, Amsterdam.
Walter, R., Havran, R. T., Schwartz, I. L., and Johnson, L. F., 1971, Interaction of D2O, Co’, Ni’ and Cu’ with oxytocin, in “Peptides, 1969. Proceedings of the Tenth European Peptide Symposium, Abano Terme, Italy, 1969” (E. Scoffone, ed.), p. 255, North-Holland, Amsterdam.
Warner, D. T., 1961. Proposed molecular models of gramicidin S and other polypeptides, Nature 190: 120.
Warner, D. T.. 1967. The use of molecular models in evaluating protein and peptide conformations, J. Am. Oil Chem. Soc. 44: 593.
Weinkam, R. J. and Jorgensen, E. C., 197la, Free radical analogs of histidine, J. Am. Chem. Soc. 93:7028
Weinkam, R. J., and Jorgensen, E. C., 1971b, Angiotensin II analogs. VIII. The use of free radical containing peptides to indicate the conformation of the carboxyl terminal region of angiotensin II. J. Am. Chem. Soc. 93: 7033.
Weinkam, R. J.. and Jorgensen, E. C., 1971c, Angiotensin II analogs. IX. Conformational studies of angiotensin II by proton magnetic resonance, J. Am. Chem. Soc. 93: 7038.
Wieland, Th., Lüben, G., Ottenheim, H., Faesel, J., de Vries, J. X., Konz, W., Prox, A., and Schmid, J., 1968, Antamanid. Seine Entdeckung, Isolierung, Strukturaufclärung und Synthese, Angew. Chem. 80: 209.
Wieland, Th., Faulstich, H., Burgermeister, W., Otting, W., Möhle, W., Shemyakin, M. M., Ovchinnikov. Yu. A., Ivanov, V. T., and Malenkov, G. G., 1970, Affinity of antamanide for sodium ions, FEBS Letters 9: 89.
Zalkin, A., Forrester, J. D.. and Templeton, D. H., 1966, Ferrichrome-A tetrahydrate. Determination of crystal and molecular structure, J. Am. Chem. Soc. 88: 1810.
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Ovchinnikov, Y.A. (1973). The Conformations of Cyclopeptides in Solution. In: Katsoyannis, P.G. (eds) The Chemistry of Polypeptides. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-4571-8_9
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