NH stretching bands of N-acetyl-(glycine, L-alanine, L-leucine)-N′-methylamides in dilute chloroform solution have shown that these dipeptides are present as a mixture of intramolecularly hydrogen-bonded five-membered ring species and nonhydrogen bonded species. Integrated absorption intensity measurements revealed that the concentration of the intramolecularly hydrogen bonded species decreased from 62% in glycine to 35% in the L-leucine derivatives.

References

1 Tsuboi, M., Shimanouchi, T. & Mizushima, S. (1959) J. Am. Chem. Soc. 81, 1406–1411.
10.1021/ja01515a031
CAS Web of Science® Google Scholar
2 Efremov, E. S., Sanyavina, L. B., Zheltova, V. N., Ivanova, A. G., Kostetskii, P. V., Ivanov, V. T., Popov, E. M. & Ovchinnikov, Yu. A. (1973) Chem. Nat. Compounds 9, 308–319.
10.1007/BF00565688
Google Scholar
3 Portnova, S. L., Bystrov, V. F., Tsetlin, V. I., Ivanov, V. T. & Ovchinnikov, Yu. A. (1968) J. Gen. Chem. 38, 424–433.
Web of Science® Google Scholar
4 Neel, J. (1972) Pure Appl. Chem. 31, 201–225.
10.1351/pac197231010201
CAS PubMed Google Scholar
5 Ginzburg, I. M. (1982) J. Gen. Chem. 52, 1445–1451.
Google Scholar
6 Hruby, V. J. (1974) in Chemistry and Biochemistry of Amino Acids, Peptides and Proteins, Vol. 3, B. Weinstein, Ed., Marcel Dekker, New York, pp. 1–188.
Google Scholar
7 Maxfield, F. R., Leach, S. J., Stimson, E. R., Powers, S. P. & Scheraga, H. A. (1979) Biopolymers 18, 2507–2521.
10.1002/bip.1979.360181010
CAS Web of Science® Google Scholar
8 Smolikova, J., Pospisek, J. & Blaha, K. (1981) Coll. Czech. Chem. Commun. 46, 772–780.
10.1135/cccc19810772
CAS Web of Science® Google Scholar
9 Chitale, S. M. & Jose, C. I. (1986) J. Chem. Soc. Faraday I 82, 663–680.
10.1039/f19868200663
CAS Web of Science® Google Scholar
10 Davis, B. D. & Khaled, Md. Abu. & Urry, D. W. (1977) J. Chem. Soc. Perkin II, 1294–1301.
Google Scholar
11 Madison, V. & Kopple, K. D. (1980) J. Am. Chem. Soc. 102, 4855–4863.
10.1021/ja00535a001
CAS Web of Science® Google Scholar
12 Zimmerman, S. S., Pottle, M. S., Nemethy, G. & Scheraga, H. A. (1977) Macromolecules 10, 1–9.
10.1021/ma60055a001
CAS PubMed Web of Science® Google Scholar
13 Apple-White, T. H. & Niemann, C. (1959) J. Am. Chem. Soc. 81, 2208–2213.
10.1021/ja01518a050
CAS Web of Science® Google Scholar
14 Blicke, F. F. & Norris, P. E. (1954) J. Am. Chem. Soc. 76, 3213–3214.
10.1021/ja01641a032
CAS Web of Science® Google Scholar
15 Ramsay, D. A. (1952) J. Am. Chem. Soc. 74, 72–80.
10.1021/ja01121a018
CAS Web of Science® Google Scholar
16 Prabhumirashi, L. S. & Jose, C. I. (1975) J. Chem. Soc. Faraday II 71, 1545–1553.
10.1039/f29757101545
CAS Web of Science® Google Scholar
17 Boussard, G., Marraud, M. & Neel, J. (1974) J. Chim. Phys. 71, 1081–1091.
CAS Web of Science® Google Scholar
18 Nyquist, R. A. (1963) Spectrochim. Acta 19, 509–519.
10.1016/0371-1951(63)80061-2
CAS Web of Science® Google Scholar
19 Ushabai, P. & Venkataramiah, K. (1971) Bull. Chem. Soc. Jpn. 44, 313–315.
10.1246/bcsj.44.313
Web of Science® Google Scholar
20 Boussard, G., Cung, M. T., Marraud, M. & Neel, J. (1974) J. Chim. Phys. 71, 1159–1166.
CAS Web of Science® Google Scholar
21 Marraud, M., Neel, J. & Avignon, M. (1970) J. Chem. Phys. 67, 959–964.
10.1051/jcp/1970670959
CAS Web of Science® Google Scholar
22 Prabhumirashi, L. S. & Jose, C. I. (1978) J. Chem. Soc. Faraday II 74, 255–262.
10.1039/f29787400255
CAS Web of Science® Google Scholar
23 Cung, M. T., Marraud, M. & Neel, J. (1974) in Conformation of Biological Molecules and Polymers, E. D. Bergmann & B. Pullman, Eds., Academic Press, New York, pp. 69–86.
Google Scholar
24 Smolikova, J., Vitek, A. & Blaha, K. (1971) Coll. Czech. Chem. Commun. 36, 2474–2485.
10.1135/cccc19712474
CAS Web of Science® Google Scholar
25 Pullman, B. & Maigret, B. (1974) in Conformation of Biological Molecules and Polymers, E. D. Bergmann & B. Pullman, Eds., Academic Press, New York, pp. 13–39.
Google Scholar
26 Bystrov, V. F., Portnova, S. L., Tsetlin, V. I., Ivanova, V. T. & Ovchinnikov, Y. A. (1969) Tetrachedron 25, 493–515.
10.1016/S0040-4020(01)83261-0
CAS PubMed Web of Science® Google Scholar
27 Renugopalkrishnan, V., Nir, S. & Rein, R. (1976) Environmental Effects on Molecular Structure and Properties, Reidel Dordecht, pp. 109–133.
10.1007/978-94-010-1837-1_8
Google Scholar
28 Solkan, V. N. & Bystrov, V. F. (1974) Bull. Acad. Sci. USSR 23, 1232–1236.
10.1007/BF00923086
Web of Science® Google Scholar
29 Gavrilov, Y. D., Solkan, V. N. & Bystrov, V. F. (1975) Bull. Acad. Sci. USSR 24, 2368–2373.
10.1007/BF00921649
Web of Science® Google Scholar

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Volume26, Issue8

August 1987

Pages 1315-1325

Ir spectra and conformational behavior of N-acetyl-(glycine, L-alanine, L-leucine)-N′-methylamides in chloroform^†

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Ir spectra and conformational behavior of N-acetyl-(glycine, L-alanine, L-leucine)-N′-methylamides in chloroform†

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Ir spectra and conformational behavior of N-acetyl-(glycine, L-alanine, L-leucine)-N′-methylamides in chloroform^†