TY - JOUR
T1 - Synthesis, Conformational Analysis, and Complexation Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog
AU - Bordes, Alexandra
AU - Poveda, Ana
AU - Troadec, Thibault
AU - Franconetti, Antonio
AU - Ardá, Ana
AU - Perrin, Flavie
AU - Ménand, Mickaël
AU - Sollogoub, Matthieu
AU - Guillard, Jerôme
AU - Désiré, Jérôme
AU - Tripier, Raphaël
AU - Jiménez-Barbero, Jesús
AU - Blériot, Yves
N1 - Publisher Copyright:
© 2020 American Chemical Society.
PY - 2020/3/20
Y1 - 2020/3/20
N2 - 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.
AB - 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.
UR - https://www.scopus.com/pages/publications/85082045543
U2 - 10.1021/acs.orglett.0c00503
DO - 10.1021/acs.orglett.0c00503
M3 - Article
C2 - 32153195
AN - SCOPUS:85082045543
SN - 1523-7060
VL - 22
SP - 2344
EP - 2349
JO - ORGANIC LETTERS
JF - ORGANIC LETTERS
IS - 6
ER -