title: Stereochemical differentiation in the Simmons-Smith reaction for cyclopropanated glucopyranose derivatives as molecular probes for glycosidases.
abstract: Glucopyranose analogues carrying a bicyclo[4.1.0]heptane framework and the diastereomer of the cyclopropane moiety were synthesized as the unit for molecular probes to mimic the unstable transition state conformation of the glucopyranose ring in enzymatic hydrolysis. The synthesis features differentiation of the α- and β-stereoselectivity in cyclopropanation of the corresponding cyclohexene derivative.
authors: Faculty of Agriculture and Life Science, Hirosaki University, Japan.
authors: Nanako
authors: N
authors: Akiyama
authors: Shogo
authors: S
authors: Noguchi
authors: Masaru
authors: M
authors: Hashimoto
mesh_terms: D003521:Cyclopropanes / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry*; D006026:Glycoside Hydrolases / Q000737:chemistry*; D006868:Hydrolysis; D008958:Models, Molecular; D008968:Molecular Conformation; D015335:Molecular Probes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003521:Cyclopropanes; D015335:Molecular Probes; C030797:cyclopropane; D006026:Glycoside Hydrolases; D005947:Glucose