Angewandte Chemie - International Edition p. 9043 - 9048 (2019)
Update date:2022-08-04
Topics:
Tu, Julian
Svatunek, Dennis
Parvez, Saba
Liu, Albert C.
Levandowski, Brian J.
Eckvahl, Hannah J.
Peterson, Randall T.
Houk, Kendall N.
Franzini, Raphael M.
The isocyano group is a structurally compact bioorthogonal functional group that reacts with tetrazines under physiological conditions. Now it is shown that bulky tetrazine substituents accelerate this cycloaddition. Computational studies suggest that dispersion forces between the isocyano group and the tetrazine substituents in the transition state contribute to the atypical structure–activity relationship. Stable asymmetric tetrazines that react with isonitriles at rate constants as high as 57 L mol?1 s?1 were accessible by combining bulky and electron-withdrawing substituents. Sterically encumbered tetrazines react selectively with isonitriles in the presence of strained alkenes/alkynes, which allows for the orthogonal labeling of three proteins. The established principles will open new opportunities for developing tetrazine reactants with improved characteristics for diverse labeling and release applications with isonitriles.
View MoreRudong Zhenfeng Yiyang Chemical Co., Ltd.
Contact:0513-84573047
Address:South Fengli Town, Rudong County, Jiangsu Province, China
Kaymossy BioChem Tech Co., Ltd
website:http://www.kaimosi.com
Contact:0571-87191913/0571-87199097
Address:Room 215, Building 3rd, No.288 Ningxia Road, Qingdao city, China
Luzhou North Chemical Co., Ltd.
Contact:+86-830-2796784;+86-830-2796776
Address:Gaoba, Longmatan District, Luzhou, Sichuan Province
Henan Yellow River New Material Technology Co.Ltd.
website:http://www.yellowriverchem.com
Contact:0086-373-7278760
Address:Chengguan Town, Yuanyang County
Contact:+86-0592 5353131
Address:No.56 Guani Road Software Park 2,Siming District
Doi:10.1021/jo071272o
(2007)Doi:10.1002/chem.201102936
(2012)Doi:10.1002/anie.200700816
(2007)Doi:10.1016/j.tet.2007.04.102
(2007)Doi:10.1021/ja071698k
(2007)Doi:10.1021/jo00206a023
(1985)