非铜催化点击化学构建电活性糖醌复合物用以检测糖—蛋白质特异识别
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摘要
非铜催化的环辛炔与叠氮环加成反应在生物化学中的应用越来越受到人们的关注,此反应简单易行,无需加入会产生细胞毒素作用的金属催化剂,被广泛应用于生物正交反应中。凝集素是一种能与糖脂或糖蛋白中糖基特异性结合的蛋白质,糖与蛋白质的这种相互作用是细胞粘附、信号传导、免疫应答、增殖和分化等多种细胞识别过程的基础。本课题设计并拟合成含环辛炔结构的一系列蒽醌类衍生物,通过非铜催化的点击反应高效构建系列糖醌复合物,并在微波催化下优化反应条件,提高反应产率。随后通过以石墨烯作为介导的π-π堆叠作用,将所合成化合物特异吸附到印刷电极上,并应用电化学方法检测其与特异凝集素的相互作用,以期进一步构建一个简易研究糖生物学的电化学平台。
The application of Cu-free click cycloaddition reaction has taken our attentions in biochemistry. This reaction is simple without the addition of the catalyst and widely used in bioorthogonal chemical reaction. Lectin is a kind of specific protein which can identify and combine with saccharide in glycoprotein and glucolipid. Carbohydrate-protein interaction is the fundamental of many cellular processes, such as cell adhesion, signal transduction, immune response, proliferation and differentiation. We designed and synthesized a series of benzoquinone alkyne derivatives containing cyclooctene, constructing a series of saccharide-quinone complexves via Cu-free click cycloaddition reaction. The appliation of microwave irradiation resulted in a significant acceleration of the reactions as well as in increased yields. A highly efficient screen printed electrode was obtained by using covalent attachment between products adsorbing on the graphene oxide and the screen printed electrode. By the electrochemical probing of specific carbohydrate-protein recognitions, we will build a simple electrochemical platform to study the glycobiology.
The application of Cu-free click cycloaddition reaction has taken our attentions in biochemistry. This reaction is simple without the addition of the catalyst and widely used in bioorthogonal chemical reaction. Lectin is a kind of specific protein which can identify and combine with saccharide in glycoprotein and glucolipid. Carbohydrate-protein interaction is the fundamental of many cellular processes, such as cell adhesion, signal transduction, immune response, proliferation and differentiation. We designed and synthesized a series of benzoquinone alkyne derivatives containing cyclooctene, constructing a series of saccharide-quinone complexves via Cu-free click cycloaddition reaction. The appliation of microwave irradiation resulted in a significant acceleration of the reactions as well as in increased yields. A highly efficient screen printed electrode was obtained by using covalent attachment between products adsorbing on the graphene oxide and the screen printed electrode. By the electrochemical probing of specific carbohydrate-protein recognitions, we will build a simple electrochemical platform to study the glycobiology.
引文
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[18]Blake C.C., L.N.Johnson, G.A. Mair, D.C. Phillips, and R. Sarma. Crystallographic studies of the activity of hen egg-white lysozyme[J]. Annual Review of Biophysics and Biomolecular Structure,1967,167:378-388
[19]Hindsgaul O., T. Norberg, J. Le Pendu, and R.U. Lemieux. Synthesis of type 2 human bloodgroup antigenic determinants.The H,X, and Y haptens and variations of the H type 2 determinant as probes for the combining site of the lectin I of Ulex europaeus[J]. Carbohydrate Research,1982,109:109-142
[20]张礼和,王梅祥.化学生物学进展[M]化学工业出版杜,2005：101-103
[21]Ambrosi M., N. R. Cameron, and B.G. Davis. Lectins:tools for the molecular understanding of the glycocode[J]. Organic & Biomolecular Chemistry,2005, 3(9):1593-1608
[22]Lis H., and N. Sharon. Lectins:carbohydrate-specific proteins that mediate cellular recognition[J]. Chemical Review,1998,98(2):637-674
[23]Sharon N., and H. Lis., History of lectins:from hemagglutinins to biological recognition molecules[J]. Glycobiology,2004,14(12):53R-62R
[24]Boyd W.C., and E. Shapleigh. Specific precipitating activity of plant agglutinins [J]. Science,1954,119:419
[25]Zelensky A.N., and J.E. Gready. The C-type lectin-like domain superfamily[J]. FEBS Journal,2005,272:6179-6217
[26]Baronde S.H., D.N.W. Cooper, M.A. Gitt, and H. Leffler. Galectins:structure and function of a large family of animal lectins[J]. Journal of Biological Chemistry,1994, 269:20807-20810
[27]Salvati A.L., A. Lahm, and G. Paonessa. Interleukin-6 antagonism by soluble 1L-6 receptor mutated in the predicted gp130 binding interface[J]. Journal of Biological Chemistry,1995,270(20):12242-12249
[28]姚守拙.压电化学与生物传感器[M].湖南师范大学出版社,1997：42-43
[29](美)Bard A.J., Faulkner L.R.著,邵元华,朱果逸,董献堆,张柏林译.电化学方法原理和应用(第二版)[M].化学工业出版社,2005：1
[30]Jackson D.R., S. Omanovic, S.G. Roscoe. Electrochemical studies of the adsorption behavior of serum proteins on titanium[J]. Langmuir,2000,16(12):5449-5457
[31]Liu S., L. Bakovic, and A. Chen A. Specific binding of glycoproteins with poly(aniline boronic acid) thin film[J]. Journal of Electroanalytical Chemistry,2006,591(2):210-216
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