Establishment of practical determination method of absolute configuration based on induced circular dichroism and quantum chemical approach to elucidation of its origin

2016 Fiscal Year Final Research Report

• Project/Area Number: 26460019
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Kyoto Pharmaceutical University
• Principal Investigator: Hosoi Shinzo 京都薬科大学, 薬学部, 教授 (60209236)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Keywords: 誘起円二色性 / ビナフチル / 絶対配置決定法 / ステロール / デカリン / 発色団 / 立体選択的合成 / キラリティー

Outline of Final Research Achievements

In order to enlarge the versatility of “the induced exciton coupled circular dichroism method”, we have carried out the followings. 1) The twelve chiral stereoisomers of 2-naphthalenols were prepared and the CD spectra of the corresponding binaphthyl esters were obtained. For the six stereoisomers of decahydro-4a-methyl-2-naphthalenol, the CD spectra of the binaphthyl ester derivatives show the bisignate CD signal with an expected sign, in which the positive for 2S-isomer and the negative for 2R-isomer. However, the other two isomers give rise to an opposite signal to the expectation, 2) We have applied this method to determine the absolute configuration of rhododenol, which has the melanogenesis suppressing activity. The CD spectra of the rhododenol derivatives have shown a split CD, indicating the potential application of the method proposed here.

Free Research Field

医歯薬学