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

[Image: see text] 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 w...

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Detalles Bibliográficos
Autores principales: Bordes, Alexandra, Poveda, Ana, Troadec, Thibault, Franconetti, Antonio, Ardá, Ana, Perrin, Flavie, Ménand, Mickaël, Sollogoub, Matthieu, Guillard, Jerôme, Désiré, Jérôme, Tripier, Raphaël, Jiménez-Barbero, Jesús, Blériot, Yves
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7114874/
https://www.ncbi.nlm.nih.gov/pubmed/32153195
http://dx.doi.org/10.1021/acs.orglett.0c00503
Descripción
Sumario:[Image: see text] 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.

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