Summary
A number of protected di- and tripeptides containing nitroarginine and proline residues, and also some derivatives of nitroarginine, have been synthesized and their IR spectra have been recorded in dilute chloroform solution. The results of the IR spectroscopy have been interpreted in the sense of the formation of an intermolecular hydrogen bond between the imino group of the side chain of nitroarginine and the carbonyl group of the following proline residue.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
E. Schroeder and K. Lubke, The Peptides, Academic Press (1965).
G. I. Chipens, in: The Chemistry and Biology of Peptides [in Russian], Riga (1971), p. 23.
R. É. Vegner, G. I. Chipens, V. E. Klusha, and Z. P. Auna, Khim. Prirodn. Soedin., 516 (1973).
J. P. Carver and E. R. Blout, in: Treatise on Collagen, Vol. 1, edited by G. N. Ramachandran, Academic Press (1967).
B. Maigret, D. Perahia, and B. Pullman, J. Mol. Biol.,29, 275 (1970).
B. Pullman, J. L. Coubeils, P. Courriere, and D. Perahia, Theor. Chim. Acta,22, 11 (1971).
G. V. Nikiforovich, I. P. Buevich, and S. G. Galaktionov, Izv. Akad. Nauk BelorussSSR, Ser. Biol., 53 (1971).
A. Damiani, P. De Santis, and A. Pizzi, Nature,226, 542 (1970).
M. Maigret, B. Pullman, and J. Caillet, Biochem. Biophys. Res. Commun.,40, 808 (1970).
J. A. Schellman and C. Schellman, Proteins,2, 45 (1964).
L. Bellamy, Infrared Spectra of Complex Molecules, 1st ed., Methuen, London (1954).
J. H. Bryden, L. A. Burkardt, E. W. Hughes, and J. Donohue, Acta Cryst.,9, 573 (1956).
M. Tichy, Advan. Org. Chem.,5, 115 (1965).
R. Schwyzer and H. Kappeler, Helv. Chim. Acta,46, 1550 (1963).
J. T. Edsall, P. J. Flory, J. C. Kendrew, A. M. Liquori, G. Nemethy, G. N. Ramachandran, and H. A. Scheraga, Biopolymers,4, 121 (1966); J. Biol. Chem.,241, 1004 (1966); J. Mol. Biol.,15, 399 (1966).
P. K. Ponnuswamy, A. V. Lakshminarayanan, and V. Sasisekharan, Biochim. Biophys. Acta,229, 596 (1971).
C. Ramakrishnan and N. Prasad, Int. J. Prot. Res.,3, 209 (1971).
P. J. Flory, Statistical Mechanics of Chain Molecules, Interscience (1969), p. 284.
S. K. Mazumdar, K. Venkatesan, and A. V. Lakshminarayanan, J. Mol. Biol.,15, 232 (1966).
C. M. Deber, F. A. Bovey, J. P. Carver, and E. R. Blout, J. Amer. Chem. Soc.,92, 6191 (1970).
Additional information
Institute of Organic Synthesis, Academy of Sciences of the Latvian SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 763–768, November–December, 1973.
Rights and permissions
About this article
Cite this article
Vegner, R.É., Chipens, G.I. & Dipan, I.V. A study of the structure of nitroarginylproline by IR spectroscopy. Chem Nat Compd 9, 730–734 (1973). https://doi.org/10.1007/BF00565797
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/BF00565797