A Concise Synthesis of a BODIPY-Labeled Tetrasaccharide Related to the Antitumor PI-88

Molecules. 2021 May 14;26(10):2909. doi: 10.3390/molecules26102909.

Abstract

A convergent synthetic route to a tetrasaccharide related to PI-88, which allows the incorporation of a fluorescent BODIPY-label at the reducing-end, has been developed. The strategy, which features the use of 1,2-methyl orthoesters (MeOEs) as glycosyl donors, illustrates the usefulness of suitably-designed BODIPY dyes as glycosyl labels in synthetic strategies towards fluorescently-tagged oligosaccharides.

Keywords: 1,2-methyl orthoesters; BODIPY; PI-88; fluorescent labeling; glycosylation.

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Boron Compounds / chemistry*
  • Glycosylation
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Oligosaccharides / pharmacology
  • Spectrometry, Fluorescence
  • Staining and Labeling*
  • Stereoisomerism

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Antineoplastic Agents
  • Boron Compounds
  • Oligosaccharides
  • phosphomannopentaose sulfate