Synthesis of peptides with alpha,beta-dehydroamino acids. XIII photoisomerization of Ac-(Z)-delta Phe-NHMe: Ac-(E)-delta Phe-NHMe

Chem Pharm Bull (Tokyo). 2000 Feb;48(2):296-7. doi: 10.1248/cpb.48.296.

Abstract

Easily accessible Ac-(Z)-delta Phe-NHMe was photoisomerized to so far unknown Ac-(E)-delta Phe-NHMe. Some parameters of the process leading to a diastereomeric mixture of ratio 90(Z):10(E) have been tested and the photoisomerization has been carried out on a preparative milligram scale. The isomers were separated via crystallization followed by preparative HPLC.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Crystallization
  • Isomerism
  • Magnetic Resonance Spectroscopy
  • Peptides / chemical synthesis*
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / chemical synthesis
  • Phenylalanine / chemistry
  • Phenylalanine / radiation effects
  • Photochemistry
  • Stereoisomerism

Substances

  • Peptides
  • acetyl-alpha,beta-dehydrophenylalanine methylamide
  • Phenylalanine