Synthesis, Conformational Analysis, and Complexation Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog
Alexandra Bordes, Ana Poveda, Thibault Troadec, Antonio Franconetti, Ana Ardá, Flavie Perrin, Mickaël Ménand, Matthieu Sollogoub, Jérôme Guillard, Jérôme Désiré, Raphaël Tripier, Jesús Jiménez‐Barbero, Yves Blériot
Abstract
High Resolution Image Download MS PowerPoint Slide A new family of chiral C 2 symmetric tetraazamacrocycles, coined ISAC for IminoSugar Aza-Crown, incorporating two iminosugars adopting a 4 C 1 conformation is disclosed. Multinuclear NMR experiments on the corresponding Cd 2+ 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 Cu 2+ in solution, with enhanced stability compared to the Cu–cyclam complex.