Development of determination method of absolute configuration using binaphthyl CD probe and its application to natural products

点击翻译按钮获取中文摘要

The induced circular dichroism (ICD) method was proven to be practical and applicable to natural products: 1) various types of unsaturated sterols were hydrogenated 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: positive chirality; 3R: negative one). This should contribute significantly to the analysis of metabolites of various types of sterols. 2) a novel CD chromophoric agent having two reaction sites was designed and applied to chiral secondary alcohols. The intensity of Cotton effects was found to be twice more than that of the monoester. 3) its application to D, L-cycloserines was examined: D-cycloserine derivative with an (R)-configuration showed positive exciton chirality whereas the L-cycloserine derivative with an (S)-configuration exhibited a negative one. It will be a powerful tool to determine the absolute configurations of various natural products with an amino group.