Stereoselective synthesis of Psi[CH(2)O] pseudodipeptides and conformational analysis of a PhePsi[CH(2)O]Ala containing analogue of the drug desmopressin

Bioorg Med Chem Lett. 2002 Mar 25;12(6):841-4. doi: 10.1016/s0960-894x(02)00016-1.

Abstract

A method for synthesis of XaaPsi[CH(2)O]Ala/Gly pseudodipeptides in good yields and excellent diastereoselectivity from azido alcohols and (R)-2-chloropropionic acid or tert-butyl bromoacetate has been developed. Insertion of one of the pseudodipeptide building blocks in the peptide drug desmopressin revealed that methylene ether isosteres may have only a minor influence on the secondary structure of peptides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Collagen Type II / analogs & derivatives
  • Deamino Arginine Vasopressin / analogs & derivatives*
  • Dipeptides / chemical synthesis*
  • Dipeptides / chemistry
  • Ethers / chemistry
  • Hemostatics / chemistry
  • Molecular Conformation
  • Molecular Mimicry
  • Stereoisomerism

Substances

  • Collagen Type II
  • Dipeptides
  • Ethers
  • Hemostatics
  • Deamino Arginine Vasopressin