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

Alexandra BordesAna PovedaThibault TroadecAntonio FranconettiAna ArdáFlavie PerrinMickaël Ménand Matthieu SollogoubJerôme GuillardJérôme DésiréPr Raphael Tripier Jiménez-Barbero Jesús Yves Blériot

Published in: Organic letters (2020)

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.

Keyphrases

molecular dynamics simulations
magnetic resonance
ionic liquid
capillary electrophoresis
molecular dynamics
high resolution
crystal structure
nk cells
solid state
mass spectrometry
single molecule