Syntheses of sugar-related trihydroxyazepanes from simple carbohydrates and their activities as reversible glycosidase inhibitors

• Published in: Carbohydrate research Vol. 326; no. 1; pp. 22 - 33
• Main Authors: Andersen, Søren M, Ekhart, Christian, Lundt, Inge, Stütz, Arnold E
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 19.05.2000; Elsevier
• Subjects: Animals; Azepines - chemical synthesis; Azepines - pharmacology; Biochemistry & Molecular Biology; Carbohydrates - chemical synthesis; Carbohydrates - chemistry; Cattle; Chemistry; Chemistry, Applied; Chemistry, Organic; Enzyme Inhibitors - chemical synthesis; Enzyme Inhibitors - pharmacology; Glycosidase inhibitors; Glycoside Hydrolases - antagonists & inhibitors; Life Sciences & Biomedicine; Molecular Conformation; Physical Sciences; Science & Technology; Simple carbohydrates; Structure-Activity Relationship; Trihydroxy azepanes; Glycosidase inhibitors; Trihydroxy azepanes; Simple carbohydrates; GLUCOSE-ISOMERASE; STEREOISOMERS; ALDONOLACTONES; AZASUGARS; ISOMERIZATION; DEOXYIMINOALDITOLS; simple carbohydrates; trihydroxy azepanes; glycosidase inhibitors
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/S0008-6215(00)00018-5

Five diastereomeric trideoxy-1,6-iminohexitols were synthesised, and their inhibitory activities were determined against selected glycosidases. For comparison, 1,4,5-trideoxy-1,5-imino- d- lyxo-hexitol, the 4-deoxy derivative of 1-deoxymannojirimicin, was prepared by enzymatic isomerisation of 6-azido-3,6-dideoxy- d- ribo-hexose into the corresponding 2-ulose and subsequent hydrogenation accompanied by intramolecular reductive amination.