Synthesis of novel glycophanes derived from glucuronic acid by ring closing alkene and alkyne metathesis

Carbohydrate Research
Dearbhla Doyle, Paul V Murphy

Abstract

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.

References

Jan 11, 2000·The Journal of Organic Chemistry·A FürstnerR Mynott
Jun 20, 2001·Bioorganic & Medicinal Chemistry Letters·M C MonneeR M Liskamp
Dec 4, 2003·Current Opinion in Chemical Biology·Michiel A LeeuwenburghHerman S Overkleeft
Apr 28, 2005·Carbohydrate Research·Paul V MurphyTrinidad Velasco-Torrijos
Aug 22, 2006·Current Medicinal Chemistry·Luca GentilucciFederico Squassabia
Sep 20, 2006·ChemMedChem·Wim MeutermansBernd Becker

Citations

Nov 12, 2009·Chemical Communications : Chem Comm·Hongxue HuangXinmiao Liang
Oct 23, 2018·Chemistry : a European Journal·Henrike Ehrhorn, Matthias Tamm
Jan 29, 2013·Angewandte Chemie·Alois Fürstner

Related Concepts

Pentenes
Carbohydrate Linkage
Sugars
Catalysis
Glycosides
Hydrogen
Hemocompatibility Testing
In Vivo NMR Spectroscopy
Phenylenediamines
Glucuronic Acid, 6-(14)C-labeled, (D)-isomer

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