title: Novel approach to determining the absolute configurations at the C3-positions of various types of sterols based on an induced circular dichroism.
abstract: Circular dichroism (CD) spectra of the 2,2'-binaphthyl ester derived from Δ(5)-sterols showed not bisignate CD but diagnostic CD bands at around 210 and 240 nm. These bands might be attributable to an interaction between an olefinic chromophore and a binaphthyl one. Various types of unsaturated sterols were thus derivatized followed by complete hydrogenation, to give saturated sterols. As a result, CD spectra of the binaphthyl derivatives of the saturated sterols showed bisignate curves centered at 240 nm (3S(β): positive chirality; 3R(α): negative one). This suggested a straightforward and practical method for discriminating the absolute stereogenic center at the C-3 positions of sterols based on an induced CD. This finding should contribute significantly to the analysis of metabolites of various types of sterols.
authors: Kyoto Pharmaceutical University, 1 Shichono-cho, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan.
authors: Toshio
authors: T
authors: Fujiwara
authors: Yuka
authors: Y
authors: Taniguchi
authors: Yukiteru
authors: Y
authors: Katsumoto
authors: Takeyuki
authors: T
authors: Tanaka
authors: Minoru
authors: M
authors: Ozeki
authors: Hiroki
authors: H
authors: Iwasaki
authors: Manabu
authors: M
authors: Node
authors: Masayuki
authors: M
authors: Yamashita
authors: Shinzo
authors: S
authors: Hosoi
mesh_terms: D002942:Circular Dichroism / Q000379:methods*; D006865:Hydrogenation; D013056:Spectrophotometry, Ultraviolet; D013261:Sterols / Q000737:chemistry*
chemical_list: D013261:Sterols