Abstract
Poly(S-[(3-hydroxypropyl)-carbamoylmethyl]-L-cysteine) [poly(Cys[CamPrOH])] has been prepared by the amidation of poly(S-carbobenzoxymethyl-L-cysteine) with 3-amino-propanol, and the properties of poly(Cys[CamPrOH]) whose number-average molecular weight is 12,000 have been investigated in various aqueous mixtures. Although the conformation of poly(Cys[CamPrOH]) in H2O is close to a random coil, it can be converted into the β-conformation in D2O. The β-conformation is formed in aqueous mixtures of CH3OH, C2H5OH, iso-C3H7OH and n-C3H7OH, respectively, and its residue ellipticity at 200 nm at the highest alcohol content of the solubility limit becomes higher as the alcohol is more hydrophobic. In a 97% acetic acid solution poly(Cys[CamPrOH]) takes on the β-conformation.
Similar content being viewed by others
Article PDF
References
S. Ikeda, Biopolymers, 5, 359 (1967).
H. Maeda and S. Ikeda, Biopolymers, 10, 2525 (1971).
S. Ikeda, A. Fukutome, T. Imae, and T. Yoshida, Biopolymers, 18, 335 (1979).
H. Eisenberg, “Biological Macromolecules and Polyelectrolytes in Solution,” Oxford University Press, Oxford, 1976.
N. Lupu-Lotan, A. Yaron, A. Berger, and M. Sela, Biopolymers, 3, 625 (1965).
K. Okita, A. Teramoto, and H. Fujita, Biopolymers, 9, 717 (1970).
T. Tomiyama and S. Ikeda, Macromolecules, 12, 165 (1979).
B. S. Harrap and I. Stapleton, Biochim. Biophys. Acta, 75, 31 (1963).
S. Ikeda, T. Tanemura, and A. Kojima, J. Colloid Interface Sci., 56, 132 (1976).
W. Moffitt and J. T. Yang, Proc. Natl. Acad. Sci., U.S.A., 42, 596 (1956).
J. T. Yang, “Poly-α-amino Acids,” G. D. Fasman, Ed., Marcel Dekker, New York, N.Y., 1967, Chapter 6.
M. Calvin, J. Hermans, Jr., and H. A. Scheraga, J. Am. Chem Soc., 81, 5048 (1959).
F. E. Karasz and J. M. O’Reilly, Biopolymers, 4, 1015 (1966).
F. E. Karasz and G. E. Gajnos, Biopolymers, 15, 1939 (1976).
P. Dubin and F. E. Karasz, Biopolymers, 11, 1745 (1972).
P. Appel and J. T. Yang, Biochemistry, 4, 1244 (1965).
P. K. Sarker and P. Doty, Proc. Natl. Acad. Sci., U.S.A., 55, 981 (1966).
R. Townend, T. F. Kumosinski, S. N. Timasheff, G. D. Fasman, and B. Davidson, Biochem. Biophys. Res. Commun., 23, 163 (1966).
B. Davidson and G. D. Fasman, Biochemistry, 6, 1616 (1967).
G. Kresheck, D. Kiereber, and R. J. Albers, J. Am. Chem. Soc., 94, 8889 (1972).
G. Kresheck, H. Schneider, and H. A. Scheraga, J. Phys. Chem., 69, 3132 (1965).
G. Conio and E. Patrone, Biopolymers, 8, 57 (1969).
G. Conio, E. Patrone, and S. Brighetti, J. Biol. Chem., 245, 3335 (1970).
R. F. Epand and H. A. Scheraga, Biopolymers, 6, 1383 (1968).
M. Barteri and B. Pispisa, Biopolymers, 12, 2309 (1973).
A. Adler, R. Hoving, J. Potter, M. Wells, and G. D. Fasman, J. Am. Chem. Soc., 90, 4736 (1968).
M. Miyake, S. Akita, A. Teramoto, N. Norisuye, and H. Fujita, Biopolymers, 13, 1173 (1974).
N. Lumpu-Lotan, A. Yaron, and A. Berger, Biopolymers, 4, 365 (1966).
F. Quadrifoglio and D. W. Urry, J. Am. Chem. Soc., 90, 2760 (1968).
N.M. Tooney and G. D. Fasman, J. Mol. Biol., 36, 355 (1968).
R. F. Epand and H. A. Scheraga, Biopolymers, 6, 1551 (1968).
S. Kubota and G. D. Fasman, Biopolymers, 14, 605 (1975).
M. Mutter, H. Mutter, R. Uhmann, and E. Bayer, Biopolymers, 15, 917 (1976).
C. Toniolo, G. M. Bonora, S. Salardi, and M. Mutter, Macromolecules, 12, 620 (1979).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Tomiyama, T., Ikeda, S. The β-Conformation of Poly(S-[(3-hydroxypropyl)-carbamoylmethyl]-L-cysteine) in Aqueous Mixtures of D2O, Aliphatic Alcohols, and Acetic Acid. Polym J 12, 511–520 (1980). https://doi.org/10.1295/polymj.12.511
Issue Date:
DOI: https://doi.org/10.1295/polymj.12.511