title: Synthesis of anomeric 1,5-anhydrosugars as conformationally locked selective α-mannosidase inhibitors.
abstract: Anomeric 1,5-anhydrosugar 2 was synthesized from d-glucose derived N-Cbz protected aminodiol 8. The key step involves, acid catalyzed hydrolysis of 1,2-acetonide group in 8 to get hemiacetal that concomitantly undergoes formation of the pyranose ring by attack of C-3 hydroxyethyl group on anomeric C-1, leading to the formation of dioxabicyclo[3.2.1]octane skeleton which on hydrogenolyis gave 2. The glycosidase inhibitory activities of hydroxy- and amino-substituted anomeric 1,5-anhydrosugars 1 and 2, respectively, showed selective inhibition of α-mannosidase. These results were substantiated by molecular docking studies using WHAT IF software and AUTODOCK 4.0 program.
authors: Department of Chemistry, Garware Research Centre, University of Pune, Pune, India.
authors: Rajendra S
authors: RS
authors: Mane
authors: Sougata
authors: S
authors: Ghosh
authors: Shailza
authors: S
authors: Singh
authors: Balu A
authors: BA
authors: Chopade
authors: Dilip D
authors: DD
authors: Dhavale
mesh_terms: D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000096:biosynthesis* / Q000737:chemistry; D005947:Glucose / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D006860:Hydrogen Bonding; D008958:Models, Molecular; D013237:Stereoisomerism; D013816:Thermodynamics; D043323:alpha-Mannosidase / Q000037:antagonists & inhibitors* / Q000378:metabolism
chemical_list: D002241:Carbohydrates; D043323:alpha-Mannosidase; D005947:Glucose