Facile access to unnatural dipeptide-alcohols based on cis-2,5-disubstituted pyrrolidines

Molecules. 2015 Feb 11;20(2):2922-30. doi: 10.3390/molecules20022922.

Abstract

Well-defined unnatural dipeptide-alcohols based on a cis-2,5-disubstitued pyrrolidine backbone were synthesized from commercially available starting materials meso-diethyl-2,5-dibromoadipate, (S)-(-)-1-phenylethylamine, and phenylalaninol. The structures of these unnatural dipeptide-alcohols are supported by HRMS, 1H- and 13C-NMR spectroscopy. These unnatural dipeptide-alcohols can act as building blocks for peptidomimetics.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adipates / chemistry
  • Alcohols / chemical synthesis*
  • Alcohols / chemistry*
  • Crystallography, X-Ray
  • Dipeptides / chemical synthesis*
  • Dipeptides / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Peptidomimetics
  • Phenethylamines / chemistry
  • Phenylalanine / analogs & derivatives
  • Phenylalanine / chemistry
  • Pyrrolidines / chemistry*
  • Stereoisomerism

Substances

  • Adipates
  • Alcohols
  • Dipeptides
  • Peptidomimetics
  • Phenethylamines
  • Pyrrolidines
  • phenylalaninol
  • Phenylalanine
  • pyrrolidine