Promoting helicity in carbohydrate-containing foldamers through long-range hydrogen bonds.
A sensor system to probe the propensity of carbohydrates to induce helical structures through long-range hydrogen bonds, based on a C(2)-symmetric xylylene bis(thiourea) arrangement, is reported; the formation of intermolecular complexes with benzoate anion promotes helix uncoiling, the free energy of the process being related to helix stability.
Rodríguez-Lucena
David
D
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Apartado 553, E-41071 Sevilla, Spain.
Benito
Juan M
JM
Mellet
Carmen Ortiz
CO
García Fernández
José M
JM
D001565:Benzoates / Q000737:chemistry; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000737:chemistry*; D006860:Hydrogen Bonding; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular
D001565:Benzoates; D002241:Carbohydrates; D007202:Indicators and Reagents