2013 Fiscal Year Final Research Report
Development of determination method of absolute configuration using binaphthyl CD probe and its application to natural products
| Project/Area Number |
23590027
|
|---|
| 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)
|
|---|
| Co-Investigator(Kenkyū-buntansha) |
KATSUMOTO Yukiteru 広島大学, 大学院・理学研究科, 助教 (90351741)
|
|---|
| Project Period (FY) |
2011 – 2013
|
| Keywords | 誘起円二色性 / ビナフチル / 絶対配置決定法 / キラルアミン / 立体配座解析 / ステロール / 天然物 / キラル二級アルコール |
|---|
| Research Abstract |
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.
|
