title: Conformations of methyl 2,5-di-O-acetyl-beta-D-glucofuranosidurono-6,3-lactone and 1,2,5-tri-O-acetyl-beta-D-glucofuranurono-6,3-lactone in the crystal structure and in solution.
abstract: The single-crystal X-ray diffraction and high-resolution 1H and 13C NMR spectral data for methyl 2,5-di-O-acetyl-beta-D-glucofuranosidurono-6,3-lactone and 1,2,5-tri-O-acetyl-beta-D-glucofuranurono-6,3-lactone are reported. The lactones were synthesized as byproducts of reactions carried out to obtain methyl 1,2,3,4-tetra-O-acetyl-D-glucopyranuronate. The conformations of these lactones in the crystal structure and in solution are discussed. A 1T2-like conformation was found to be the preferred form for these lactones in both the crystal lattice and in solution.
authors.affiliation: Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, PL-80-952 Gdańsk, Poland. beatal@chem.univ.gda.pl
authors.forename: Beata
authors.initials: B
authors.lastname: Liberek
authors.forename: Dorota
authors.initials: D
authors.lastname: Tuwalska
authors.forename: Iwona do
authors.initials: Id
authors.lastname: Santos-Zounon
authors.forename: Antoni
authors.initials: A
authors.lastname: Konitz
authors.forename: Artur
authors.initials: A
authors.lastname: Sikorski
authors.forename: Zygfryd
authors.initials: Z
authors.lastname: Smiatacz
mesh_terms: D002236:Carbohydrate Conformation; D018360:Crystallography, X-Ray; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D012996:Solutions / Q000737:chemistry
chemical_list: C513755:1,2,5-tri-O-acetylglucofuranosidurono-6,3-lactone; D005960:Glucosides; D007783:Lactones; D009844:Oligosaccharides; D012996:Solutions; C513754:methyl 2,5-di-O-acetylglucofuranosidurono-6,3-lactone; C439623:1,2,3,4-tetra-O-acetylglucopyranose