Synthesis and chelation study of a fluoroionophore and a glycopeptide based on an aza crown iminosugar structure

Carbohydr Res. 2021 Mar:501:108258. doi: 10.1016/j.carres.2021.108258. Epub 2021 Feb 10.

Abstract

Capitalizing on a recently reported iminosugar-based aza-crown (ISAC) accessed by a double Staudinger azaWittig coupling reaction, we have expanded the structural diversity of this new family of sweet cyclam analogs. Replacement of the two secondary amines linking the iminosugar units by two amide bonds obtained a cyclodimerization by with BOP and DIPEA led to a macrocycle that did not demonstrate efficient Zn2+ chelation unlike the parent ISAC. Introduction of two pyrene moieties on the secondary amines of the parent ISAC yielded a new fluoroionophore that selectively binds Hg2+ in methanol.

Keywords: Iminosugar; Ionophore; Macrocycle; NMR analysis.

MeSH terms

  • Chelating Agents / chemical synthesis*
  • Chelating Agents / chemistry
  • Crown Compounds / chemistry*
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Glycopeptides / chemical synthesis*
  • Glycopeptides / chemistry
  • Imino Sugars / chemistry*
  • Molecular Conformation

Substances

  • Chelating Agents
  • Crown Compounds
  • Fluorescent Dyes
  • Glycopeptides
  • Imino Sugars