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

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.

SUBMITTER: Bordes A

PROVIDER: S-EPMC7114874 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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

Bordes Alexandra A Poveda Ana A Troadec Thibault T Franconetti Antonio A Ardá Ana A Perrin Flavie F Ménand Mickaël M Sollogoub Matthieu M Guillard Jerôme J Désiré Jérôme J Tripier Raphaël R Jiménez-Barbero Jesús J Blériot Yves Y

Organic letters 20200310 6

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 enhanc ...[more]

PMID: 32153195

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