Optimized synthesis of aminooxy-peptides as glycoprobe precursors for surface-based sugar-protein interaction studies

Bioorg Med Chem Lett. 2007 Sep 15;17(18):5155-8. doi: 10.1016/j.bmcl.2007.06.090. Epub 2007 Jul 5.

Abstract

An improved procedure for solid phase coupling of Boc-aminooxyacetic acid to peptides is described. By avoiding base-containing activation mixtures which cause over-acylation, it practically suppresses this unwanted side reaction and leads to near quantitative yields of Aoa-peptides, useful as glycoprobe precursors in glycomic studies.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrates / chemistry*
  • Chromatography, High Pressure Liquid
  • Molecular Probes*
  • Peptides / chemical synthesis*
  • Proteins / chemistry*
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • Carbohydrates
  • Molecular Probes
  • Peptides
  • Proteins