Synthesis of new peptidic glycoclusters derived from beta-alanine. Part 2: optionally modulated distance between side-chain branched points

Chem Pharm Bull (Tokyo). 2005 Sep;53(9):1131-5. doi: 10.1248/cpb.53.1131.

Abstract

The synthesis of an asymmetric glycocluster 1 has been achieved using two glycocluster units 12 and 13, prepared by coupling the cluster chain unit 4 with each omega-amino acid (beta-alanine and 6-aminocapronic acid) trichloroethyl ester, and peptidic C-terminal block glycocluster 16, prepared by coupling the bifunctional linker 14 with sugar unit 9. This method facilitated the synthesis of the cluster optionally modulated the distance between the side-chain branched points by using various omega-amino acids. We also synthesized glycodendron 2 using the same intermediate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminocaproic Acid / chemistry
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Chromatography, Thin Layer
  • Glycopeptides / chemical synthesis*
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Optical Rotation
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Spectrophotometry, Ultraviolet
  • beta-Alanine / chemistry*

Substances

  • Glycopeptides
  • Indicators and Reagents
  • beta-Alanine
  • Aminocaproic Acid