Effect of structural and conformation modifications, including backbone cyclization, of hydrophilic hexapeptides on their intestinal permeability and enzymatic stability.

@article{Hess2007EffectOS,
  title={Effect of structural and conformation modifications, including backbone cyclization, of hydrophilic hexapeptides on their intestinal permeability and enzymatic stability.},
  author={Shmuel Hess and O. Ovadia and D. Shalev and Hanoch Senderovich and Bashir Qadri and Tamar Yehezkel and Y. Salitra and T. Sheynis and R. Jelinek and C. Gilon and A. Hoffman},
  journal={Journal of medicinal chemistry},
  year={2007},
  volume={50 24},
  pages={
          6201-11
        }
}
  • Shmuel Hess, O. Ovadia, +8 authors A. Hoffman
  • Published 2007
  • Chemistry, Medicine
  • Journal of medicinal chemistry
  • A library of 18 hexapeptide analogs was synthesized, including sub-libraries of N- or C-methylation of the parent hexapeptide Phe-Gly-Gly-Gly-Gly-Phe, as well as backbone cyclized analogs of each linear analog with various ring sizes. N- or C-methylation as well as cyclization (but not backbone cyclization) have been suggested to improve intestinal permeability and metabolic stability of peptides in general. Here we aimed to assess their applicability to hydrophilic peptides. The intestinal… CONTINUE READING
    59 Citations

    Topics from this paper

    The effect of multiple N-methylation on intestinal permeability of cyclic hexapeptides.
    • 92
    Novel method for the synthesis of urea backbone cyclic peptides using new Alloc‐protected glycine building units
    • 26

    References

    SHOWING 1-10 OF 49 REFERENCES
    Backbone cyclization: A new method for conferring conformational constraint on peptides
    • 163
    Effect of peptide conformation on membrane permeability.
    • 26
    Facile synthesis of orthogonally protected amino acid building blocks for combinatorial N-backbone cyclic peptide chemistry.
    • 26
    Testing the conformational hypothesis of passive membrane permeability using synthetic cyclic peptide diastereomers.
    • 258
    • PDF
    Intestinal metabolism and absorption of cholecystokinin analogs in rats.
    • 10