Synthesis of novel glycophanes derived from glucuronic acid by ring closing alkene and alkyne metathesis.
Cyclophanes and their analogues are of interest in bioactive molecule development and in biomimetic, supramolecular and materials chemistry. Novel hybrids of sugars and cyclophanes (glycophanes) have been prepared via the coupling of alkenyl and alkynyl glucopyranosiduronic acids with phenylene-1,4-diamine and xylene-1,4-diamine and subsequent intramolecular metathesis. Structural studies showed that the geometric arrangements of the sugar groups in the macrocycles containing secondary amides differ from those in macrocycles that contain tertiary amides. This is due to the amides adopting different configurational preferences. The compounds had low solubility in water, precluding an investigation of their recognition phenomena in this medium.
Doyle
Dearbhla
D
Centre for Synthesis and Chemical Biology, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland.
Murphy
Paul V
PV
D000475:Alkenes / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002621:Chemistry / Q000379:methods; D020723:Glucuronic Acid / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis*; D006859:Hydrogen / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008422:Materials Testing; D008956:Models, Chemical; D008968:Molecular Conformation; D010655:Phenylenediamines / Q000138:chemical synthesis*
D000475:Alkenes; D002241:Carbohydrates; D006027:Glycosides; D010655:Phenylenediamines; D006859:Hydrogen; D020723:Glucuronic Acid