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

Alexandra Bordes (1) , Ana Poveda (2) , Thibault Troadec (3) , Antonio Franconetti (2) , Ana Arda (2) , Flavie Perrin (1) , Mickaël Ménand (4) , Matthieu Sollogoub (4) , Jérôme Guillard (1) , Jerome Desire (1) , Raphaël Tripier (3) , Jesus Jimenez-Barbero (2, 5, 6) , Yves Blériot (1)

1 IC2MP [Poitiers] - Institut de chimie des milieux et matériaux de Poitiers [UMR 7285]
2 CICbioGUNE - Cell Biology and Stem Cells Unit
3 CEMCA - Chimie, Electrochimie Moléculaires et Chimie Analytique
4 IPCM - Institut Parisien de Chimie Moléculaire
5 Ikerbasque - Basque Foundation for Science
6 UPV / EHU - University of the Basque Country = Euskal Herriko Unibertsitatea

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.

Mots clés: Redox reactions; Carbohydrates; Conformation; Cations; Macrocycles

Domaines: Chimie organique; Chimie de coordination

Alexandra Bordes, Ana Poveda, Thibault Troadec, Antonio Franconetti, Ana Arda, et al.. Synthesis, Conformational Analysis, and Complexation Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog. Organic Letters, 2020, 22 (6), pp.2344-2349. ⟨10.1021/acs.orglett.0c00503⟩. ⟨hal-02504835⟩