Synthesis of a Chiral and Fluorescent Sugar-Based Macrocycle by 1,3-Dipolar Cycloaddition

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 δ-amino acid with a glutamic acid propargylic amide derivative, followed by coupling of the sugar δ-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.

Key words

azides - amino acids - cycloadditions - macrocycles - carbohydrates

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MacroModel 8.5, MMFFs force field with water as solvent, 20 000 steps, all backbone torsions were selected for random variation.