Design, synthesis and photochemical properties of caged bile acids.
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.
Hirayama
Yuuki
Y
Department of Biomolecular Science, Toho University, 2-2-1 Miyama, Funabashi 274-8510, Japan.
Iwamura
Michiko
M
Furuta
Toshiaki
T
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
D000080:Acetals; D002793:Cholic Acids; D009578:Nitrobenzenes; D006913:Hydroxysteroid Dehydrogenases