2011 Fiscal Year Final Research Report
Probe for bio-oligomers and elucidation of their function
| Project/Area Number |
21550160
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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 |
Chemistry related to living body
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| Research Institution | Nagasaki University |
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Principal Investigator |
MAKI Toshihide 長崎大学, 産学官連携戦略本部, 准教授 (10291535)
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| Project Period (FY) |
2009 – 2011
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| Keywords | 質量分析用分子標識剤 / 光開裂性分子 / エーテル結合形成 / ベンジル化 |
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| Research Abstract |
General procedures for derivatization of multi functionalized bio-oligomers and exploitation of new function to capture a target molecules connecting photocleavable molecular tag were achieved in this research.
Along with the experiment, a new synthetic route for the photocleavable molecular tag for laser desorption ionization mass spectrometry(LDI-MS) was achieved using Fries reaction of 2, 6-dimethylphenyl ester as its key reaction. Zirconium chloride was found as uniquely efficient adjuvant to promote the reaction. The molecular tag was obtained in 5 steps without chromatographic purification.
And, the Benzylation of hydroxyl groups in the presence of tertiary amines is established. A mixture of an alcohol and a benzyl halide afforded the corresponding benzyl ether in good to excellent yields in the presence of diisopropylethylamine. The importance of solventless conditions was observed. The reaction showed high tolerance to many functional groups including benzoate, even at a reaction temperature of 150°C. Sodium iodide was found to be an efficient catalyst to accelerate the reaction. The simple operation was successfully applied for pre-treatment of LDI-MS analysis.
Then, new trapping agent for sugars targeting 1, 2-diol motif by mean of ketal formation reaction. Photocleavable molecular tag bearing alpha diketone functioality was designed and synthesized. Since the compound does not have redundant tether substructure, high sensitivity is comparable with compounds previously prepared.
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