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
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      References

      SHOWING 1-10 OF 49 REFERENCES
      Effect of Restricted Conformational Flexibility on the Permeation of Model Hexapeptides Across Caco-2 Cell Monolayers
      • 52
      Synthesis and biological activity of NK-1 selective, N-backbone cyclic analogs of the C-terminal hexapeptide of substance P.
      • 52
      The Influence of Peptide Structure on Transport Across Caco-2 Cells. II. Peptide Bond Modification Which Results in Improved Permeability
      • 96
      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
      A backbone-cyclic, receptor 5-selective somatostatin analogue: synthesis, bioactivity, and nuclear magnetic resonance conformational analysis.
      • 52
      Intestinal metabolism and absorption of cholecystokinin analogs in rats.
      • 10
      Structural Specificity of Mucosal-Cell Transport and Metabolism of Peptide Drugs: Implication for Oral Peptide Drug Delivery
      • 93
      • PDF