Tetrazine ligation: Fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity

被引：1280

作者：

Blackman, Melissa L. ^{[1
]}

Royzen, Maksim ^{[1
]}

Fox, Joseph M. ^{[1
]}

机构：

[1] Univ Delaware, Dept Chem & Biochem, Brown Labs, Newark, DE 19716 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 41期

关键词：

D O I：

10.1021/ja8053805

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Described is a bioorthogonal reaction that proceeds with unusually fast reaction rates without need for catalysis: the cycloaddition of s-tetrazine and trans-cyclooctene derivatives. The reactions tolerate a broad range of functionality and proceed in high yield in organic solvents, water, cell media, or cell lysate. The rate of the ligation between trans-cyclooctene and 3,6-di-(2-pyridyl)-s-tetrazine is very rapid (k(2) 2000 M-1 s(-1)). This fast reactivity enables protein modification at low concentration.

引用

页码：13518 / +

页数：3

共 37 条

[1] A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems [J].

Agard, NJ ;

Prescher, JA ;

Bertozzi, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15046-15047

[2] INHIBITION OF HUMAN NEUTROPHIL ELASTASE WITH PEPTIDYL ELECTROPHILIC KETONES .2. ORALLY-ACTIVE P-G-VAL-PRO-VAL PENTAFLUOROETHYL KETONES [J].

ANGELASTRO, MR ;

BAUGH, LE ;

BEY, P ;

BURKHART, JP ;

CHEN, TM ;

DURHAM, SL ;

HARE, CM ;

HUBER, EW ;

JANUSZ, MJ ;

KOEHL, JR ;

MARQUART, AL ;

MEHDI, S ;

PEET, NP .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (26) :4538-4553

[3] Transition metal catalyzed methods for site-selective protein modification [J].

Antos, John M. ;

Francis, Matthew B. .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2006, 10 (03) :253-262

[4] Copper-free click chemistry for dynamic in vivo imaging [J].

Baskin, Jeremy M. ;

Prescher, Jennifer A. ;

Laughlin, Scott T. ;

Agard, Nicholas J. ;

Chang, Pamela V. ;

Miller, Isaac A. ;

Lo, Anderson ;

Codelli, Julian A. ;

Bertozzi, Carolyn R. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (43) :16793-16797

[5] DIELS-ALDER REACTIONS OF HETEROCYCLIC AZADIENES - SCOPE AND APPLICATIONS [J].

BOGER, DL .

CHEMICAL REVIEWS, 1986, 86 (05) :781-793

[6] Site-specific labeling of proteins with small molecules in live cells [J].

Chen, I ;

Ting, AY .

CURRENT OPINION IN BIOTECHNOLOGY, 2005, 16 (01) :35-40

[7] Second-generation difluorinated cyclooctynes for copper-free click chemistry [J].

Codelli, Julian A. ;

Baskin, Jeremy M. ;

Agard, Nicholas J. ;

Berozzi, Carolyn R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (34) :11486-11493

[8] Synthesis of N-(β-D-glucopyranosyl) monoarnides of dicarboxylic acids as potential inhibitors of glycogen phosphorylase [J].

Czifrak, Katalin ;

Hadady, Zsuzsa ;

Doesa, Tibor ;

Gergely, Pal ;

Schmidt, Juergen ;

Wessjohann, Ludger ;

Somsak, Laszlo .

CARBOHYDRATE RESEARCH, 2006, 341 (08) :947-956

[9] Diels-Alder ligation and surface immobilization of proteins [J].

de Araújo, AD ;

Palomo, JM ;

Cramer, J ;

Köhn, M ;

Schröder, H ;

Wacker, R ;

Niemeyer, C ;

Alexandrov, K ;

Waldmann, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (02) :296-301

[10] Site-specific, covalent attachment of proteins to a solid surface [J].

Duckworth, Benjamin P. ;

Xu, Juhua ;

Taton, T. Andrew ;

Guo, Athena ;

Distefano, Mark D. .

BIOCONJUGATE CHEMISTRY, 2006, 17 (04) :967-974

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