Journal of Biosciences

, Volume 8, Issue 1–2, pp 223–238 | Cite as

A guest-host approach to oligodepsipeptide structure

  • M. Goodman
  • Y. V. Venkatachalapathi
  • S. Mammi
  • R. Katakai


In this paper we investigate the effect of main chain isosteric replacement of specific amino acid residues by α-hydroxy acids. As part of a long term program specifically protected heptaglutamates were prepared and their circular dichroism and nuclear magnetic resonance spectra in various solvents were examined. From these experiments conformational preferences were deduced. We have also prepared oligo-(γ-methyl-glutamates) replacing the amino acids at specific positions along the chain with S-lactic acid and have elucidated the effect of these main chain isosteric replacements on oligopeptide structure.

Analogues of collagen also have been prepared with glycolic acid replacing specific glycine residues. We synthesized the model hexamers Ac-Ala-Gly-Pro-Ala-Gly-Pro-NHMe, Ac-Ala-Glc-Pro-Ala-Gly-Pro-NHMe, and Ac-Ala-Gly-Pro-Ala-Glc-Pro-NHMe in order to study their structural characteristics under various conditions. Preliminary nuclear magnetic resonance and circular dichroism results are presented.


Oligodepsipeptides nuclear magnetic resonance circular dichroism hydrogen bonding 

Abbreviations used


Nuclear magnetic resonance


circular dichroism






Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Becktel, W. J., Mathias, L. J. and Goodman, M. (1980)Macromolecules,14, 203.CrossRefGoogle Scholar
  2. Goodman, M., Verdini, A. S., Toniolo, C, Phillips, W. D. and Bovey, A. (1969)Proc. Natl. Acad. Sci. USA,64, 444.CrossRefGoogle Scholar
  3. Goodman, M., Becktel, W. J., Katakai, R. and Wouters, G. (1980)Makromol. Chem. Suppl.,4, 100.CrossRefGoogle Scholar
  4. Katakai, R. and Goodman, M. (1982)Macromolecules,15, 25.CrossRefGoogle Scholar
  5. Naider, F., Sipzner, R., Steinfeld, A. S., Becker, J. M., Ribeiro, A. A. and Goodman, M. (1979) inProceedings of the 6th American Peptide Symposium (eds E. Gross and J. Meienhofer) (Rockford: Pierce Chemical Co.) p. 185.Google Scholar
  6. Pysh, E. S. and Toniolo, C. (1977)J. Am. Chem. Soc.,99, 6211.CrossRefGoogle Scholar
  7. Ribeiro, A. A., Goodman, M. and Naider, F. (1978)J. Am. Chem. Soc.,100, 3903.CrossRefGoogle Scholar
  8. Ribeiro, A. A., Saltman, R. P. and Goodman, M. (1980)Biopolymers,19, 1771.CrossRefGoogle Scholar

Copyright information

© Indian Academy of Sciences 1985

Authors and Affiliations

  • M. Goodman
    • 1
  • Y. V. Venkatachalapathi
    • 1
  • S. Mammi
    • 1
  • R. Katakai
    • 1
    • 2
  1. 1.Department of Chemistry, B-014University of California, San DiegoLa JollaUSA
  2. 2.Department of Chemistry, College of TechnologyGunma UniversityKiryu-shiJapan

Personalised recommendations