Rational design of improved dienophiles for in vivo tetrazine-trans-cyclooctene ligation

被引：1

作者：

Stauch, Tim ^{[1
]}

Scholtes, Jan Felix ^{[2
]}

Dreuw, Andreas ^{[1
]}

机构：

[1] Interdisciplinary Ctr Sci Comp, Neuenheimer Feld 205, D-69120 Heidelberg, Germany

[2] Inst Organ Chem, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

来源：

CHEMICAL PHYSICS LETTERS | 2016年 / 654卷

关键词：

COPPER-FREE; BASIS-SETS; CHEMISTRY; CYCLOADDITION; RESOLUTION; ENERGY; CELLS; TAGS; CIS;

D O I：

10.1016/j.cplett.2016.04.044

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The inverse electron-demand Diels-Alder reaction of trans-cyclooctene and sym-tetrazine is a bioorthogonal reaction which has found widespread applications during the last decade, e.g. for fluorescent labeling of living cells. However, the use of this reaction is still limited due to the rapid isomerization of trans-cyclooctene to its unreactive cis-conformer. Using computational methods, we have derived two optimized derivatives of trans-cyclooctene, which pave the road to more efficient in vivo labeling of arbitrary proteins. (C) 2016 Elsevier B.V. All rights reserved.

引用

页码：6 / 8

页数：3

共 35 条

[1] Design and Synthesis of Highly Reactive Dienophiles for the Tetrazine trans-Cyclooctene Ligation
Taylor, Michael T.
Blackman, Melissa L.
Dmitrenko, Olga
Fox, Joseph M.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (25) : 9646 - 9649
[2] Development of a 11C-labeled tetrazine for rapid tetrazine-trans-cyclooctene ligation
Herth, Matthias M.
Andersen, Valdemar L.
Lehel, Szabolcs
Madsen, Jacob
Knudsen, Gitte M.
Kristensen, Jesper L.
CHEMICAL COMMUNICATIONS, 2013, 49 (36) : 3805 - 3807
[3] Development of an 11C-labeled tetrazine for rapid tetrazine-trans-cyclooctene ligation
Herth, Matthias M.
Andersen, Valdemar L.
Lehel, Szabolcs
Madsen, Jacob
Knudsen, Gitte M.
Kristensen, Jesper L.
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2013, 56 : S88 - S88
[4] Tetrazine-trans-cyclooctene - trans-cyclooctene ligation: Unveiling the chemistry and applications within the human body
Tomarchio, Elisabetta Grazia
Turnaturi, Rita
Saccullo, Erika
Patamia, Vincenzo
Floresta, Giuseppe
Zagni, Chiara
Rescifina, Antonio
BIOORGANIC CHEMISTRY, 2024, 150
[5] Homodimeric Protein-Polymer Conjugates via the Tetrazine-trans-Cyclooctene Ligation
Lorenzo, Maltish M.
Decker, Caitlin G.
Kahveci, Muhammet U.
Paluck, Samantha J.
Maynard, Heather D.
MACROMOLECULES, 2016, 49 (01) : 30 - 37
[6] Tetrazine-trans-cyclooctene ligation for the rapid construction of 18F labeled probes
Li, Zibo
Cai, Hancheng
Hassink, Matthew
Blackman, Melissa L.
Brown, Richard C. D.
Conti, Peter S.
Fox, Joseph M.
CHEMICAL COMMUNICATIONS, 2010, 46 (42) : 8043 - 8045
[7] Tetrazine-trans-cyclooctene ligation (TTCO ligation) for the rapid construction of 18F labeled probes
Li, Zibo
Selvaraj, Ramajeyam
Huang, Chiun-Wei
Hassink, Matthew
Cai, Hancheng
Blackman, Melissa
Fox, Joseph
Conti, Peter
JOURNAL OF NUCLEAR MEDICINE, 2011, 52
[8] Decorating DNA with boronic acids through tetrazine-trans-cyclooctene cycloaddition
Wang, Ke
Wang, Danzhu
Ji, Kaili
Chen, Weixuan
Zheng, Yueqin
Dai, Chaofeng
Wang, Binghe
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[9] Efficient 18F Labeling of Cysteine-Containing Peptides and Proteins Using Tetrazine-Trans-Cyclooctene Ligation
Liu, Shuanglong
Hassink, Matthew
Selvaraj, Ramajeyam
Yap, Li-Peng
Park, Ryan
Wang, Hui
Chen, Xiaoyuan
Fox, Joseph M.
Li, Zibo
Conti, Peter S.
MOLECULAR IMAGING, 2013, 12 (02): : 121 - 128
[10] Conformationally strained trans-cyclooctene with improved stability and excellent reactivity in tetrazine ligation
Darko, Ampofo
Wallace, Stephen
Dmitrenko, Olga
Machovina, Melodie M.
Mehl, Ryan A.
Chin, Jason W.
Fox, Joseph M.
CHEMICAL SCIENCE, 2014, 5 (10) : 3770 - 3776

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