Synthesis of glycolipopeptidic building blocks for carbohydrate receptor discovery

Carbohydr Res. 2011 Sep 6;346(12):1439-44. doi: 10.1016/j.carres.2011.03.019. Epub 2011 Mar 15.

Abstract

A class of glycolipopeptides for use as building blocks for a new type of dynamic combinatorial library is reported. The members of the library consist of a variable carbohydrate moiety, coded amino acids, and lipoamino acids in order to convert them into amphiphiles. Glycolipopeptidic amphiphiles interact through non-covalent bonding when mixed together in aqueous phase and form micelles in dynamic close-packed fluid mosaic arrays. The head groups of amphiphiles are exposed on the micelle surface, providing entities which could be screened in biological assays to find the most potent combination of building blocks in order to identify new bioactive carbohydrate ligands.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry
  • Chromatography, High Pressure Liquid
  • Combinatorial Chemistry Techniques / methods*
  • Drug Discovery / methods*
  • Drug Interactions
  • Glycoproteins / chemistry
  • High-Throughput Screening Assays / methods*
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Micelles
  • Peptide Library
  • Receptors, Cell Surface / chemistry
  • Receptors, Cell Surface / metabolism
  • Small Molecule Libraries / chemical synthesis*
  • Small Molecule Libraries / metabolism
  • Spectrometry, Mass, Electrospray Ionization
  • Surface-Active Agents / chemical synthesis*
  • Surface-Active Agents / metabolism

Substances

  • Amino Acids
  • Glycoproteins
  • Ligands
  • Micelles
  • Peptide Library
  • Receptors, Cell Surface
  • Small Molecule Libraries
  • Surface-Active Agents