title: An approach to 8 stereoisomers of homonojirimycin from (D)-glucose via kinetic & thermodynamic azido-γ-lactones.
abstract: Crystal structures were obtained for the two C2 epimeric azido-γ-lactones 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d-ido-heptono-1,4-lactone and 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d-gulo-heptono-1,4-lactone prepared from kinetic and thermodynamic azide displacements of a triflate derived from d-glucoheptonolactone. Azido-γ-lactones are very useful intermediates in the synthesis of iminosugars and polyhydroxylated amino acids. In this study two epimeric azido-heptitols allow biotechnological transformations via Izumoring techniques to 8 of the 16 possible homonojirimycin analogues, 5 of which were isolated pure because of the lack of stereoselectivity of the final reductive amination. A side-by-side glycosidase inhibition profile of 11 of the possible 16 HNJ stereoisomers derived from d-glucose and d-mannose is presented.
authors: Oxford Glycobiology Institute, University of Oxford, South Parks Road, Oxford, OX1 3QU, UK.
authors: Andreas F G
authors: AF
authors: Glawar
authors: Sarah F
authors: SF
authors: Jenkinson
authors: Scott J
authors: SJ
authors: Newberry
authors: Amber L
authors: AL
authors: Thompson
authors: Shinpei
authors: S
authors: Nakagawa
authors: Akihide
authors: A
authors: Yoshihara
authors: Kazuya
authors: K
authors: Akimitsu
authors: Ken
authors: K
authors: Izumori
authors: Terry D
authors: TD
authors: Butters
authors: Atsushi
authors: A
authors: Kato
authors: George W J
authors: GW
authors: Fleet
mesh_terms: D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry*; D007700:Kinetics; D007783:Lactones / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D001386:Azides; D007783:Lactones; C106502:homonojirimycin; D017485:1-Deoxynojirimycin; D005947:Glucose