Thermotropic liquid-crystalline peptide derivatives: oligo(glutamic acid)s forming hydrogen-bonded columns

Org Biomol Chem. 2005 Mar 7;3(5):875-80. doi: 10.1039/b416474a. Epub 2005 Feb 2.

Abstract

We report on new thermotropic liquid-crystalline oligo(amino acid) derivatives forming columnar structures. These are based on branched oligo(glutamic acid)s and 2-(3,4-dialkyloxyphenyl)ethyl moieties. An oligo(glutamic acid) derivative, alpha,gamma-bis(L-glutamoyl) L-glutamic acid tetra[2-(3,4-dioctadecyloxyphenyl)ethyl]ester, shows a hexagonal columnar phase, whilst a glutamic acid derivative, alpha,gamma-bis[2-(3,4-dioctadecyloxyphenyl)ethyl] L-glutamate, does not show a mesophase. Hydrogen bonds formed by the oligo(glutamic acid) moieties should contribute to the induction of the columnar liquid-crystalline properties. In addition, we have examined the effects of the molecular chirality of the oligo(glutamic acid) parts and the functionalisation at the focal position of the taper shaped molecules on the liquid-crystalline properties of the compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkanes / chemistry
  • Amides / chemistry
  • Calorimetry, Differential Scanning
  • Ethers / chemistry
  • Fatty Acids / chemistry
  • Glutamic Acid / chemistry*
  • Hydrogen Bonding
  • Liquid Crystals / chemistry*
  • Microscopy, Polarization
  • Models, Molecular
  • Molecular Structure
  • Oligopeptides / chemical synthesis
  • Oligopeptides / chemistry*
  • Phase Transition
  • Spectrophotometry, Infrared
  • Transition Temperature
  • X-Ray Diffraction

Substances

  • Alkanes
  • Amides
  • Ethers
  • Fatty Acids
  • Oligopeptides
  • Glutamic Acid