Development of general chiral method for chiral branched-chain carboxylic acids
| Project/Area Number |
11660100
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
Bioproduction chemistry/Bioorganic chemistry
|
|---|
| Research Institution | TOHOKU UNIVERSITY |
|---|
Principal Investigator |
AKASAKA Kazuaki Graduate School of Life Sciences, Tohoku University, Assistant professor, 大学院・生命科学研究科, 助教授 (10201881)
|
|---|
| Co-Investigator(Kenkyū-buntansha) |
OHMI Hiroshi Graduate School of Life Sciences, Tohoku University, Professor, 大学院・生命科学研究科, 教授 (20100050)
|
|---|
| Project Period (FY) |
1999 – 2001
|
| Project Status |
Completed (Fiscal Year 2001)
|
| Budget Amount *help |
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2001: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 2000: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1999: ¥1,800,000 (Direct Cost: ¥1,800,000)
|
|---|
| Keywords | determination of the absolute configuration / ateiso fatty acide / chiral fluorescent derivatization reagent / chiral discrimination of methylbranched fatty acides / chiral discrimination on HPLC / 分岐脂肪酸 / 絶対配置の決定 / 蛍光不斉誘導体化 / キラル分離 / 分岐脂肪酸、 / 絶対配置の決定、 / キラル分離、 |
|---|
| Research Abstract |
Methyl branched-chain fatty acids and alcohols were found in many natural products, but it had been very difficult or practically impossible to discriminate the enantiomers with very small amounts of samples. In this study, we developed general method to discriminate chiral carboxylic acids with very high sensitiovity by using a novel chiral fluorescent labeling reagent. Anteiso fatty acids having 5 to 29 carbon atoms were labelled with chiral fluorescent derivatization reagents, (1R,2R)- and (1S,2S)-2-(2,3-anthracenedicarboximido) cyclohexanol. The diastereomeric derivatives up to C20 anteiso acids were separated into two peaks on ODS column under low column temperature conditions, while those having more than C21 could not be separated by the system. The C30 column made it possible to separate diastereomeric derivatives of up to C29 anteiso acids. There was empirical rule on the elution order of diastereomeric derivatives, and it allowed us to determine the absolute configuration of the branched-chain carboxylic acids by using both enantiomers of the reagents. This method made it possible to determine absolute configurations of methyl branched fatty acids in a novel ceramide isolated from the Epiphytic Dinoflagellate Coollia monotis and glycoglycerolipid S365A isolated from Corynebacterium aquaticum, and it made also possible to determine absolute configuration at the two cyclopropane moieties of plakoside A, an immunosuppressive marine galactosphingolipid.
|
Report
(4 results)
Research Products
(5 results)
