title: Conformationally locked thiosugars as potent alpha-mannosidase inhibitors: synthesis, biochemical and docking studies.
abstract: A series of thiosugar derivatives (thiolevomannosans) derived from mannose were synthesized and their inhibitory activity was tested against alpha-mannosidase (jack bean). These inhibitors were found to be more potent than the well-known inhibitors like kifunensine and deoxymannojirimycin based on docking and biochemical studies. The sulfone derivative 10 was shown to be the best inhibitor of alpha-mannosidase with the K(i) value of 350 nM.
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Bangalore, Karnataka, India.
authors.forename: K
authors.initials: K
authors.lastname: Sivapriya
authors.forename: S
authors.initials: S
authors.lastname: Hariharaputran
authors.forename: V L
authors.initials: VL
authors.lastname: Suhas
authors.forename: N
authors.initials: N
authors.lastname: Chandra
authors.forename: S
authors.initials: S
authors.lastname: Chandrasekaran
mesh_terms: D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006860:Hydrogen Bonding; D008024:Ligands; D008958:Models, Molecular; D008968:Molecular Conformation; D012451:Safrole / Q000031:analogs & derivatives / Q000737:chemistry; D013329:Structure-Activity Relationship; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013450:Sulfones / Q000737:chemistry; D043323:alpha-Mannosidase / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism*
chemical_list: D002241:Carbohydrates; D004791:Enzyme Inhibitors; D008024:Ligands; D013438:Sulfhydryl Compounds; D013450:Sulfones; D043323:alpha-Mannosidase; D012451:Safrole; C005746:sulfoxide