Recent knowledge and innovations related to hexofuranosides: structure, synthesis and applications.
Hexofuranosides are widely spread in nature, and notably in numerous pathogenic microorganisms. This particular five-membered ring for hexosides leads to novel biological properties and, as usual in glycochemistry, to completely different reactivity and selectivity. Far from being exhaustive, this review will first focus on the structure of the oligosaccharidic part of hexofuranosyl conjugates found in natural sources. Original syntheses will then be presented, stressing more particularly on the development of chemical and chemo-enzymatic tools for the access to 1,2-trans or 1,2-cis linkages. Finally, innovative applications related to biological, chemical and physicochemical fields for both natural and synthetic hexofuranosyl compounds will be described.
Peltier
Pauline
P
Ecole Nationale Supérieure de Chimie de Rennes, Organic and Supramolecular Chemistry, UMR CNRS 6226, Avenue du Général Leclerc, F-35700 Rennes, France.
Euzen
Ronan
R
Daniellou
Richard
R
Nugier-Chauvin
Caroline
C
Ferrières
Vincent
V
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D000970:Antineoplastic Agents / Q000737:chemistry; D001105:Archaea / Q000737:chemistry; D001419:Bacteria / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D056890:Eukaryota / Q000737:chemistry; D005658:Fungi / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D006027:Glycosides / Q000737:chemistry*; D006601:Hexoses / Q000737:chemistry*; D019751:Intramolecular Transferases / Q000037:antagonists & inhibitors; D008969:Molecular Sequence Data; D009169:Mycobacterium tuberculosis / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry; D010944:Plants / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D013215:Starfish / Q000737:chemistry; D013865:Thioglycosides / Q000737:chemistry / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D005663:Furans; D006027:Glycosides; D006601:Hexoses; D009844:Oligosaccharides; D013865:Thioglycosides; D006026:Glycoside Hydrolases; D019751:Intramolecular Transferases; C098051:UDP-galactopyranose mutase