Synthesis and photo-activity of peptide nucleic acids containing an azobenzene unit
Synthesis and photo-activity of peptide nucleic acids containing an azobenzene unit
摘要
We prepared the azobenzene PNA unit and synthesized various PNAs containing an azobenzene unit by a typical tBoc method. Both the azobenzene PNA unit and PNA containing an azobenzene unit (N-PNA) showed reversible photoisomerization with UV and visible light irradiation. The hybridization of N-PNA with complementary DNA resulted in a considerable decrease of the photoisomerization rate constant of the azobenzene.
We prepared the azobenzene PNA unit and synthesized various PNAs containing an azobenzene unit by a typical tBoc method. Both the azobenzene PNA unit and PNA containing an azobenzene unit （N-PNA） showed reversible photoisomerization with UV and visible light irradiation. The hybridization of N-PNA with complementary DNA resulted in a considerable decrease of the photoisomerization rate constant of the azobenzene.
基金
Supported by the Major State Basic Research Development Program of China (Grant No. 2007CB607605)
National Natural Science Foundation of China (Grant No. 20473106)
关键词
偶氮苯
肽核酸
单位
合成
照片
光异构化
可见光照射
互补DNA
peptide nucleic acid （PNA）, azobenzene, photoisomerization, photoisomerization rate constant
参考文献10
-
1Clivio P,,Guillaume D,Adeline M T, et al.Synthesis and photo- chemical behavior of peptide nucleic acid dimers and analogues containing 4-thiothymine: Unprecedented photoadduct reversion[].Journal of the American Chemical Society.1998
-
2Wilhelmsson L M,Holmen A,Lincoln P, et al.A highly fluorescent DNA base analogue that forms Watson-Crick base pairs with guanine[].Journal of the American Chemical Society.2001
-
3Challa H,Wosk S A.Solution phase synthesis of potential DNA-binding molecules based on the PNA backbone[].Tetrahedron Letters.1999
-
4Willner I.Photoswitchable biomaterials: En route to optobioelectro- nic systems[].Accounts of Chemical Research.1997
-
5Liang X,Asanuma H,Kashida H, et al.NMR study on the photoresponsive DNA tethering an azobenzene. assignment of the absolute configuration of two diastereomers and structure determination of their duplexes in the trans-form[].Journal of the American Chemical Society.2003
-
6Nielsen PE,Egholm M,Berg RH,et al.Sequence-selective recognition of DNA by strand displacement with a thymine-substituted polyamide[].Science.1991
-
7Hyrup,B,Nielsen,PE.Peptide nucleic acids (PNA): synthesis, properties and potential applications[].Bioorganic and Medicinal Chemistry.1996
-
8Ausín,C.,Ortega,J-A.,Robles,J.,Grandas,A.,Pedroso,E.Synthesis of amino- and guanidino-G-clamp PNA monomers[].Organic Letters.2002
-
9A. Okamoto,K. Tanabe,I. Saito.Synthesis and properties of peptide nucleic acids containing a psoralen Unit[].Organic Letters.2001
-
10Eldrup,A.B.,Dahl,O.,Nielsen,P.E.A novel peptide nucleic acid monomer for recognition of thymine in triple helix structures[].Journal of the American Chemical Society.1997
-
1徐绍红,夏然,杨西宁,渠桂荣.微波辅助下离子液体中肽核酸前体-碱基乙酸酯的合成[J].河南师范大学学报（自然科学版）,2009,37(5):162-164. 被引量：2
-
2褚征,刘克良.肽核酸的合成、修饰和应用[J].有机化学,2005,25(3):254-263. 被引量：4
-
3贾涛,姜中兴,石闯,李早英.肽核酸骨架分子键联卟啉的合成及结构表征[J].有机化学,2006,26(2):223-227. 被引量：2
-
4李进都,陈淼,张浩波,刘胜,刘建喜.原子力显微镜研究包含偶氮苯的肽核酸与纳米颗粒标记DNA的杂交[J].科学通报,2008,53(10):1235-1237. 被引量：2
-
5莫毅,郭亚芬,兰干球,窦璋琴,兰虹丞,蒋钦杨,杨秀荣,蒋和生,李柏.广西巴马小型猪卵泡抑素(Follistatin)cDNA的克隆和序列分析[J].广西农业生物科学,2005,24(2):99-103. 被引量：8
-
6贾涛,姜中兴,石闯,李早英.卟啉-肽核酸骨架分子的合成[J].有机化学,2003,23(z1).
-
7Rong-Yan Yang,Chun-Yan Bao,Qiu-Ning Lin,Lin-Yong Zhu.A light-regulated synthetic ion channel constructed by an azobenzene modified hydraphile[J].Chinese Chemical Letters,2015,26(7):851-856.
-
8常艳兵,舒有良,张银烽,李晓飞,杨云慧.基于量子点标记的可卡因适体传感器的研制[J].云南化工,2010,37(5):1-6.
-
9张海黔,篠原宽明,顾宁,佐々木裕司,宍户昌彦.Cell Adhesion Inhibition by RGD Peptides Linked with a Photoisomerizable Nonnatural Amino Acid[J].Journal of Southeast University(English Edition),2001,17(2):22-26.
-
10孟庆国,许笑宇,梁远军,刘克良.含羟基和咪唑基团新手性肽核酸的设计与合成[J].有机化学,2006,26(6):845-847. 被引量：1
