title: Transformation of quercitols into 4-methylenecyclohex-5-ene-1,2,3-triol derivatives, precursors for the chemical chaperones N-octyl-4-epi-β-valienamine (NOEV) and N-octyl-β-valienamine (NOV).
abstract: (+)-proto-Quercitol (1) and (-)-vibo-quercitol (2), both of which could be readily prepared by the bioconversion of myo-inositol, were successfully converted into the corresponding 4-methylenecyclohex-5-ene-1,2,3-triol derivatives. These compounds were demonstrated to be suitable precursors, preserving their configurations, for bioactive carba-aminosugars such as the potent chemical chaperone drug candidates, N-octyl-4-epi-β-valienamine (NOEV, 3) and N-octyl-β-valienamine (NOV, 4).
authors: Central Research Laboratories, Hokko Chemical Industry Co. Ltd, Toda, Atsugi, Japan. kuno-s@hokkochem.co.jp
authors: Shinichi
authors: S
authors: Kuno
authors: Atsushi
authors: A
authors: Takahashi
authors: Seiichiro
authors: S
authors: Ogawa
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry; D000818:Animals; D002240:Carbohydrate Sequence; D002417:Cattle; D003510:Cyclohexanes / Q000737:chemistry*; D004440:Ecdysone / Q000031:analogs & derivatives / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000737:chemistry; D006595:Hexosamines / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008099:Liver / Q000201:enzymology; D008752:Methylene Chloride / Q000737:chemistry*; D008969:Molecular Sequence Data; D013329:Structure-Activity Relationship
chemical_list: D000814:Aniline Compounds; D003510:Cyclohexanes; D004791:Enzyme Inhibitors; D006595:Hexosamines; C116532:N-octyl-beta-valienamine; C483225:proto-quercitol; C518949:vibo-quercitol; C051218:3,5,14-trihydroxycholest-7-en-6-one; D004440:Ecdysone; C506365:Cyclohexane; D007294:Inositol; D008752:Methylene Chloride; C023650:aniline