7-羟基香豆素氨基酸衍生物的合成及表征
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- 英文论文题名：Synthesis and Characterization of Derivatives of 7-Hydroxycoumarin Amino Acids
- 论文作者：喻思思 ; 官召兵 ; 杨蕾 ; 胡晓松
- 英文论文作者：Sisi Yu ; Zhaobing Guan ; Lei Yang ; Xiaosong Hu ; Department of chemistry ; School of Chemistry ; Chemical Engineering and Life Sciences ; Wuhan University of Technology
- 年：2016
- 作者机构：武汉理工大学化学化工与生命科学学院化学系;
- 论文关键词：香豆素氨基酸 ; 衍生化 ; 结构表征 ; 紫外吸收光谱 ; 荧光性能
- 会议召开时间：2016-07-01
- 会议录名称：中国化学会第30届学术年会摘要集-第二十七分会：光化学
- 语种：中文
- 分类号：O629.71;O657.3
- 学会代码：ZGHY
- 会议名称：中国化学会第30届学术年会-第二十七分会 ; 光化学
- 会议地点：中国辽宁大连
- 主办单位：中国化学会
- 学会名称：中国化学会
- 页数：1
- 文件大小：230k
- 原文格式：D
- 会议级别：全国
摘要
香豆素类氨基酸具有荧光量子产率高,Stoke’s位移大,体积较小,并且对外界pH及溶剂极性变化很敏感,可以较好地满足生物学研究中荧光标记的需求。Peter G.Schultz研究组通过改造蛋白质翻译过程中的氨酰-t RNA合成酶(aminoacyl-t RNAsynthetase,aa RS)和t RNA首先实现了含有7-羟基香豆素氨基酸的蛋白质的遗传编码表达,此后该氨基酸在生物学研究领域得到了广泛的应用。本文介绍了7-羟基香豆素氨基酸的两种衍生物的合成、纯化和结构表征。研究表明,我们所采用的合成和纯化方法能够方便有效地得到这些香豆素氨基酸衍生物。这些化合物的在不同pH值的缓冲溶液中紫外吸收光谱和荧光光谱表明它们具有和7-羟基香豆素氨基酸不同的荧光特征,可以在筛选出其对应的氨酰-t RNA合成酶和t RNA后极大地扩展了香豆素类非天然氨基酸在生物学研究中应用范围。
The high fluorescence quantum yield, large Stoke's shift, small size, sensitivity to pH and solvent polarity makes it a good candidate for the fluorescent labeling in biological studies. Since the first genetic incorporation of 7-hydroxycoumarin amino acid into proteins by the Peter G. Schultz group, more and more applications of it in biological research have been carried out. Two derivatives of 7-hydroxycoumarin amino acid were synthesized and purified. Their structures were confirmed by NMR spectroscopy. Results show that our synthetic and purification method can provide them with high yield and purity. The UV absorption and fluorescent spectroscopy of these two derivatives at different pH value shows that they have different fluorescent properties compared with 7-hydroxycoumarin amino acid, which will extend the range of applications of coumarin type non-natural amino acids in biological studies once the aminoacyl-t RNAsynthetase/t RNA pairs for them are successfully evolved.
The high fluorescence quantum yield, large Stoke's shift, small size, sensitivity to pH and solvent polarity makes it a good candidate for the fluorescent labeling in biological studies. Since the first genetic incorporation of 7-hydroxycoumarin amino acid into proteins by the Peter G. Schultz group, more and more applications of it in biological research have been carried out. Two derivatives of 7-hydroxycoumarin amino acid were synthesized and purified. Their structures were confirmed by NMR spectroscopy. Results show that our synthetic and purification method can provide them with high yield and purity. The UV absorption and fluorescent spectroscopy of these two derivatives at different pH value shows that they have different fluorescent properties compared with 7-hydroxycoumarin amino acid, which will extend the range of applications of coumarin type non-natural amino acids in biological studies once the aminoacyl-t RNAsynthetase/t RNA pairs for them are successfully evolved.
引文
[1]Wang,J.Xie,J.Schultz,P.G.J.Am.Chem.Soc.2006,128:8738.
[2]Lacey,V.K.;Parrish,A.R.;Han,S.;Shen,Z.;Briggs,S.P.;Ma,Y.;Wang,L.Angew.Chem.,Int.Ed.2011,50:8692.
[2]Lacey,V.K.;Parrish,A.R.;Han,S.;Shen,Z.;Briggs,S.P.;Ma,Y.;Wang,L.Angew.Chem.,Int.Ed.2011,50:8692.