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

Org Lett. 2020 Mar 20;22(6):2344-2349. doi: 10.1021/acs.orglett.0c00503. Epub 2020 Mar 10.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't