Improved hemicryptophane hosts for the stereoselective recognition of glucopyranosides.
Four new enantiomerically and diastereomerically pure hemicryptophane hosts (M-SSS-2/P-SSS-2 and M-RRR-2/P-RRR-2 pairs) were designed for the recognition of sugar derivatives. Their absolute configuration was determined from the circular dichroism spectra and DFT calculations. The host molecules were then used for the stereoselective recognition of glucopyranosides. Binding constants were obtained from (1)H NMR titration experiments showing an increase of affinity for this class of receptors, associated with an improved diastereo- and enantio-differentiation.
Laboratoire de Chimie, CNRS, École Normale Supérieure de Lyon, 46, Allée d'Italie, F-69364 Lyon 07, France. alxandre.martinez@ens-lyon.fr jean-pierre.dutasta@ens-lyon.fr.
Aline
A
Schmitt
Olivier
O
Perraud
Elina
E
Payet
Bastien
B
Chatelet
Benjamin
B
Bousquet
Marion
M
Valls
Daniele
D
Padula
Lorenzo
L
Di Bari
Jean-Pierre
JP
Dutasta
Alexandre
A
Martinez
D002942:Circular Dichroism; D005960:Glucosides / Q000737:chemistry*; D007700:Kinetics; D008958:Models, Molecular; D008968:Molecular Conformation; D011083:Polycyclic Compounds / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D011789:Quantum Theory; D013237:Stereoisomerism
D005960:Glucosides; D011083:Polycyclic Compounds; C523242:cryptophane