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Conformational disturbance induced by AzPro/Pro substitution in peptides

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Summary

Consequences inherent to the substitution of aza-proline (AzPro) for proline in the octapeptide TTSAPTTS, representative of the tandem repeat motif present in the peptide backbone of MUC5AC mucin, were analysed in terms of conformational perturbation and O-glycosylation aptitude. In DMSO solution, we observed the same tendency previously noted in AzPro-tripeptide models, i.e. AzPro prevents β-turn formation in which it would occupy the i+1 position, and therefore behaves quite opposite to Pro, whereas both AzPro and Pro can support a β-turn in the i+2 position with a cis disposition of the preceding tertiary amide function. The former structural modifications do not prevent O-glycosylation to take place at the same specific site, but it occurs at a reduced rate.

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Authors and Affiliations

  1. Laboratoire de Chimie Physique Macromoléculaire, ENSIC-INPL, BP 451, F-54001, Nancy Cedex, France

    Alain Bac, Katell Rivoal, Manh Thong Cung, Guy Boussard & Michel Marraud

  2. Biologie et Physiopathologie des Cellules Mucipares, Unité INSERM No. 377, F-59045, Lille Cedex, France

    Benoît Soudan, Daniel Tetaert & Pierre Degand

Authors
  1. Alain Bac
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  2. Katell Rivoal
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  3. Manh Thong Cung
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  4. Guy Boussard
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  5. Michel Marraud
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  6. Benoît Soudan
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  8. Pierre Degand
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Bac, A., Rivoal, K., Cung, M.T. et al. Conformational disturbance induced by AzPro/Pro substitution in peptides. Lett Pept Sci 4, 251–258 (1997). https://doi.org/10.1007/BF02442885

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  • DOI: https://doi.org/10.1007/BF02442885

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