Abstract
The two side chain amino groups of the two L-ornithine residues in gramicidin-S seem to be important for the antibacterial activity of the molecule, since complete acetylation, formylation, carbamylation, deamination, trinitrophenylation, succinylation, maleylation of the antibiotic caused 90–95 % loss of the antibacterial activity of the antibiotic. However this modification leads to only 12–30% loss of the hemolytic activity. Monoacetyl- and monoformyl gramicidin-S with a free amino group retains nearly 50% of the antibacterial activity of the molecule. It seems, therefore, that the two amino groups contribute equally to the antibacterial activity of gramicidin-S
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References
Aoyagi, H., Kato, T., Ohno, M., Kondo, M. and Izumiya, N. (1964)J. Am. Chem. Soc.,86, 5700
Butler, P. J. G., Harris, J. I., Hartly, B. S. and Leberman, R. (1969)Biochem. J.,112, 679.
Dimick, K. P. (1943)J. Biol. Chem.,149, 387.
Florey, H. W., Chain, E., Heatley, N. G., Jennings, M. A., Sanders, A. G., Abraham, E. P. and Florey, M. E. (1949)Antibiotics (London: Oxford University Press) Vols. I and II.
Fraenkel-Conrat, H. and Cooper, M (1944)J. Biol. Chem.,154, 239.
Freedman, H. M., Grossberg, A. L. and Pressman, D. (1968)Biochemistry,7, 1941.
Goldfarb, A. R. (1966)Biochemistry,5, 2570.
Izumiya, N., Kato, T., Aoyagi, H., Waki, M. and Kondo, M. (1972)Synthetic aspects of biologically active peptides-gramicidin-S and tyrocidines. (A Halstead Press Book, Kodansha, Tokyo).
Katchalski, E., Berger, A., Bichowsky-Solmnitzki, L. and Kurtz, J. (1955)Nature (London),176, 118.
Okuyama, T. and Satake, K. (1960)J. Biochem. (Tokyo) 47, 454.
Rambhav, S. and Ramachandran, L. K. (1976)Indian J. Biochem. Biophys.,13, 361.
Rambhav, S. (1981) J.Biosci.,3, 221.
Rambhav, S. (1982)J. Biosci.,4, 25.
Rambhav, S. (1984)Curr. Sci.,53, 426.
Rosen, H. (1957)Arch. Biochem. Biophys.,67, 10.
Schwyzer, R. and Sieber, P. (1959)Helv. Chim. Acta.,42, 972.
Srinivasa, B. R. and Ramachandran, L. K. (1978)Indian J. Biochem. Biophys.,14, 54.
Stepanov, V. M. and Silaev, A. B. (1961)J. Gen. Chem. USSR.,31, 3556.
Ushalakshmi, S. and Ramachandran, L. K. (1969a)Biochem. J.,111, 40.
Ushalakshmi, S. and Ramachandran, L. K. (1969b)Indian J. Biochem.,6, 145.
Wooten, I. D. P. (1964) inMicro-analysis in medical biochemistry (London: J and A Churchill Ltd.) p. 92.
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Nagamurthi, G., Rambhav, S. Gramicidin-S: Structure-activity relationship. J. Biosci. 7, 323–329 (1985). https://doi.org/10.1007/BF02716794
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DOI: https://doi.org/10.1007/BF02716794