Synthesis, Conformational Analysis, and Complexation
Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog

Bordes, Alexandra; Poveda, Ana; Troadec, Thibault; Franconetti, Antonio; Ardá, Ana; Perrin, Flavie; Ménand, Mickaël; Sollogoub, Matthieu; Guillard, Jerôme; Désiré, Jérôme; Tripier, Raphaël; Jiménez-Barbero, Jesús; Blériot, Yves

doi:10.1021/acs.orglett.0c00503.s001

ol0c00503_si_001.pdf (3.85 MB)

Synthesis, Conformational Analysis, and Complexation Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog

journal contribution

posted on 2020-03-09, 20:14 authored by Alexandra Bordes, Ana Poveda, Thibault Troadec, Antonio Franconetti, Ana Ardá, Flavie Perrin, Mickaël Ménand, Matthieu Sollogoub, Jerôme Guillard, Jérôme Désiré, Raphaël Tripier, Jesús Jiménez-Barbero, Yves Blériot

A new family of chiral C₂ symmetric tetraazamacrocycles, coined ISAC for IminoSugar Aza-Crown, incorporating two iminosugars adopting a ⁴C₁ conformation is disclosed. Multinuclear NMR experiments on the corresponding Cd²⁺ complex show that the ISAC is a strong chelator in water and its tetramine cavity adopts a conformation similar to that of the parent Cd–cyclam complex. Similar behavior is observed with Cu²⁺ in solution, with enhanced stability compared to the Cu–cyclam complex.