Homochiral oligopeptides generated via an asymmetric induction in racemic 2D crystallites at the air-water interface; the system ethyl/thio-ethyl esters of long-chain amphiphilic alpha-amino acids

Chem Commun (Camb). 2005 Nov 21:(43):5432-4. doi: 10.1039/b507457f. Epub 2005 Sep 30.

Abstract

N(epsilon)-stearoyl-lysine-ethyl-ester (C18-OE-Lys) operates as an efficient desymmetrizing agent for the generation of homochiral oligopeptides via a reaction catalyzed by silver ions in two-dimensional (2D) quasi-racemic crystallites of the corresponding thio-ester (C18-TE-Lys) self-assembled on water.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Esterification
  • Hydrophobic and Hydrophilic Interactions
  • Ions / chemistry
  • Molecular Structure
  • Oligopeptides / chemistry*
  • Phase Transition*
  • Silver / chemistry
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Stereoisomerism
  • Sulfhydryl Compounds / chemistry*
  • Water / chemistry*
  • X-Ray Diffraction

Substances

  • Amino Acids
  • Ions
  • Oligopeptides
  • Sulfhydryl Compounds
  • Water
  • Silver