Synthesis of a chiral and fluorescent sugar-based macrocycle by 1,3-dipolar cycloaddition

Jenny Ågren, Johan Billing, Hans Grundberg, Ulf Nilsson

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20 Citations (SciVal)

Abstract

An efficient and modular synthesis of a chiral, amphiphilic, and fluorescent macrocycle is described. A bis-acetylene was prepared by coupling the amino group of a sugar delta-amino acid with a glutamic acid propargylic amide derivative, followed by coupling of the sugar delta-amino acid carboxy group with a glutamic acid propiolyl amide. The bis-acetylene was reacted with 9,10-bis(azidomethyl)anthracene under Cu(I) catalysis to afford the target fluorescent macrocycle.
Original languageEnglish
Pages (from-to)3141-3145
JournalSynthesis
Issue number18
DOIs
Publication statusPublished - 2006

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Subject classification (UKÄ)

  • Organic Chemistry

Keywords

  • carbohydrates
  • macrocycles
  • cycloadditions
  • azides
  • amino acids

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