Oligofuranosides containing conformationally restricted residues: synthesis and conformational analysis.
The synthesis of a panel of arabinofuranosyl oligosaccharide analogues (5-13) in which one ring is locked into either the E(3) or OE conformation is described. The E(3)-locked scaffolds 15 and 16 required for the synthesis of 5-10 were prepared in one step from known 1,5-anhydroalditols. A number of routes were explored for the preparation of the OE-locked monosaccharide derivative 17 needed for the preparation of 11-13. The successful synthesis of 17 was achieved in 17 steps from D-arabinose. Subsequent analysis of 5-13 by 1H NMR spectroscopy demonstrated that the locked residue does not exert any detectable influence upon the conformers populated by adjacent conformationally unrestricted furanose rings.
Houseknecht
Justin B
JB
Department of Chemistry, The Ohio State University, Columbus 43210, USA.
Lowary
Todd L
TL
D001089:Arabinose / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D002236:Carbohydrate Conformation; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D002855:Chromatography, Thin Layer; D003500:Cyclization; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009161:Mycobacterium / Q000201:enzymology*; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D009904:Optical Rotation; D010430:Pentosyltransferases / Q000378:metabolism*; D013237:Stereoisomerism
D004187:Disaccharides; D007202:Indicators and Reagents; D009844:Oligosaccharides; D001089:Arabinose; D010430:Pentosyltransferases; C101967:arabinosyltransferase