Sensitive Probes for Chirality Recognition by Biological Substances
| Project/Area Number |
07672284
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Josai University |
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Principal Investigator |
YAMADA Koh-ichi Josai University, Pharmaceutical Sciences, Professor, 薬学部, 教授 (70077973)
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| Co-Investigator(Kenkyū-buntansha) |
NAKAGAWA Hiroko Josai University, Pharmaceutical Sciences, Associate, 薬学部, 助手 (40118534)
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| Project Period (FY) |
1995 – 1996
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| Project Status |
Completed (Fiscal Year 1996)
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| Budget Amount *help |
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1996: ¥200,000 (Direct Cost: ¥200,000)
Fiscal Year 1995: ¥1,900,000 (Direct Cost: ¥1,900,000)
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| Keywords | thiaheterohelicene / serum albumin / active site / chiral recognition / CD spectrum / chirality conversion reaction / chiral micelle |
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| Research Abstract |
The reactions of [5] thiaheterohelicene (I) and its derivatives that act as a probe for chirality recognition were investigated with serum albumins (SA) of several species, bovine and rat serum, and chiral micelles. 1. Syntheses and evaluation of probes : I,2-hydroxymethyl-I (II), 2-carboxylic acid of I (II), and stearate of II (IV) were synthesized, which were found to be in rapid equilibrium between P and M enantiomers at room temperature in solution. 2. Second-order asymmetric transformation of III in BSA solution : BSA underwent the uptake of III molecules of which configuration was fixed only as M,in marked contrast to P in the case of II.3. Difference in chiral discrimination between SAs of several species : On application of II as a probe to aqueous solution of SAs of nine animal species, induced CD (ICD) spectra of the SA-II complexes that were produced showed large variations between the complexes, reflecting the difference in the spatial structure of the uptake site of each SA.4. Detection of ability for chiral discrimination by bovine serum : A ddition of II to bovine serum induced the intense CD absorption bands originated from II and yielded the obvious different spectra between the intact serum and the mildly preheated serum. 5. Application to diabetic rat serum : The ICD from II and the serum of diabetic rats contracted by administration of alloxan was found to have fairly smaller and broade bands than those from II and the control serum, suggesting a lowering of the ability of diabetic serum for chirality recognition. 6. Behaviors of the probe compounds in chiral micelles : The interactions of II,III and IV with chiral micelles formed with D- or L-stearoyl serine enhanced the propensity to align the molecules in the micelles by lowering the inversion rate of helicene moiety of the probe compounds.
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Report
(3 results)
Research Products
(14 results)
