Synthetic Studies and chemical research on the function of deazaflavin coenzymes and analogues
| Project/Area Number |
60470145
|
|---|
| Research Category |
Grant-in-Aid for General Scientific Research (B)
|
| Allocation Type | Single-year Grants |
|---|
| Research Field |
Chemical pharmacy
|
|---|
| Research Institution | Kyoto University |
|---|
Principal Investigator |
YONEDA Fumio Faculty of Pharmaceutical Sciences, Kyoto University, 薬学部, 教授 (80040327)
|
|---|
| Co-Investigator(Kenkyū-buntansha) |
TANAKA Kiyoshi Faculty of Pharmaceutical Sciences, Kyoto University, 薬学部, 助手 (50093266)
HARAYAMA Takashi Faculty of Pharmaceutical Sciences, Kyoto University, 薬学部, 助手 (30025712)
|
|---|
| Project Period (FY) |
1985 – 1986
|
| Project Status |
Completed (Fiscal Year 1986)
|
| Budget Amount *help |
¥5,700,000 (Direct Cost: ¥5,700,000)
Fiscal Year 1986: ¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1985: ¥3,900,000 (Direct Cost: ¥3,900,000)
|
|---|
| Keywords | Deazaflavin / Coenzyme <F_(420)> / Autorecycling oxidation / Optical activity / Asymmetric reduction / 5-Arylidene barbituric acid derivative / 核酸塩基二量化 |
|---|
| Research Abstract |
Much of renewed interest in 5-deazaflavins (5-dF) stems from their close relationship to the origin of life. Synthetic studies and chemical research on these biologically interesting 5-dF and their analogues were carried out to give the following some remarkable results.
1.A highly convergent total synthesis of coenzyme F 420 was tried and the chromophore of F 420 was successfully constracted through two different kinds of effective short step synthetic routes. The peptide containing lactate moiety was also synthesized and these two components were combined in form of phosphate ester by phosphite triester approach to afford the precursor of F 420.
2.Polycyclic deazaflavin derivatives such as (bent) double headed 5-dF, mixed flavin, pyrimidine fused 5-dF were synthesized and examined to have the superior ability as autorecycling oxidation catalyst to 5-dF.
3.Several different type of optically active 5-dFs including compounds with axial dissymmetry were prepared and applied to the asymmetric reduction of ethyl benzoylformate. Using achiral 5-dF, asymmetric reduction under chiral media (catalyst) was also investigated and moderate (0[25% e.e.) chiral induction was observed in these reduction.
4.5-Arylidene barbituric acid derivatives were found to be mild and efficient organic oxidants of thiols to disulfides as well as allylic and benzylic alcohols to the corresponding carbonyl compounds under neutral condition.
5.In connection with the function of 5-dF derivatives, 5-dFs especially those with D-ribityl moiety have great inhibitory effect on the photochemical dimerization of dimethylthymine.
|
Report
(1 results)
Research Products
(13 results)
-
-
-
-
-
-
-
-
-
[Publications] F. Yoneda et al.: "1,3,8,10,14-Hexazapentaphene-2,4,7,9(14H,3H,8H,11H)-Tetraones (Bent Double Headed 5-Deazaflavins) with Strong Oxidizing Power" Chem. Pharm. Bull.34-6. 2653-2655 (1986)
Description
「研究成果報告書概要(欧文)」より
Related Report
-
-
-
-
