title: Design, synthesis and photochemical properties of caged bile acids.
abstract: Photolabile derivatives of bile acids (8-10 and 13) were synthesized via silver (I) oxide promoted selective etherification of 3alpha-hydroxyls. Quantitative production of the parent cholic acid was detected from the photolytic mixture of 3-NB-CA (8) in Tris buffered solution. Interestingly, the unexpectedly stable nitroso-hemiacetal intermediate (14) was detected when the photolysis was conducted in methanol. The enzymatic analysis using 7alpha-HSDH showed 8 and 9 could serve as caged bile acids that might be able to regulate certain biological processes upon UV irradiation.
authors.affiliation: Department of Biomolecular Science, Toho University, 2-2-1 Miyama, Funabashi 274-8510, Japan.
authors.forename: Yuuki
authors.initials: Y
authors.lastname: Hirayama
authors.forename: Michiko
authors.initials: M
authors.lastname: Iwamura
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Furuta
mesh_terms: D000080:Acetals / Q000737:chemistry; D002793:Cholic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D015195:Drug Design; D006913:Hydroxysteroid Dehydrogenases / Q000378:metabolism; D009578:Nitrobenzenes / Q000737:chemistry; D010782:Photolysis
chemical_list: D000080:Acetals; D002793:Cholic Acids; D009578:Nitrobenzenes; D006913:Hydroxysteroid Dehydrogenases