Unknown

Dataset Information

0

Fluorogenic Bifunctional trans-Cyclooctenes as Efficient Tools for Investigating Click-to-Release Kinetics.

ABSTRACT: The inverse electron demand Diels-Alder pyridazine elimination reaction between tetrazines and allylic substituted trans-cyclooctenes (TCOs) is a key player in bioorthogonal bond cleavage reactions. Determining the rate of elimination of alkylamine substrates has so far proven difficult. Here, we report a fluorogenic tool consisting of a TCO-linked EDANS fluorophore and a DABCYL quencher for accurate determination of both the click and release rate constants for any tetrazine at physiologically relevant concentrations.

SUBMITTER: de Geus MAR 

PROVIDER: S-EPMC7496853 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Fluorogenic Bifunctional trans-Cyclooctenes as Efficient Tools for Investigating Click-to-Release Kinetics.

de Geus Mark A R MAR   Maurits Elmer E   Sarris Alexi J C AJC   Hansen Thomas T   Kloet Max S MS   Kamphorst Kiki K   Ten Hoeve Wolter W   Robillard Marc S MS   Pannwitz Andrea A   Bonnet Sylvestre A SA   Codée Jeroen D C JDC   Filippov Dmitri V DV   Overkleeft Herman S HS   van Kasteren Sander I SI  

Chemistry (Weinheim an der Bergstrasse, Germany) 20200603 44

The inverse electron demand Diels-Alder pyridazine elimination reaction between tetrazines and allylic substituted trans-cyclooctenes (TCOs) is a key player in bioorthogonal bond cleavage reactions. Determining the rate of elimination of alkylamine substrates has so far proven difficult. Here, we report a fluorogenic tool consisting of a TCO-linked EDANS fluorophore and a DABCYL quencher for accurate determination of both the click and release rate constants for any tetrazine at physiologically  ...[more]

Similar Datasets

Unknown Efficient low-cost preparation of <i>trans</i>-cyclooctenes using a simplified flow setup for photoisomerization.
| S-EPMC4785212 | biostudies-literature
Unknown Genetic Encoding of bicyclononynes and trans-cyclooctenes for site-specific protein labeling in vitro and in live mammalian cells via rapid fluorogenic Diels-Alder reactions.
| S-EPMC3687367 | biostudies-literature
Unknown Development of benzothiazole 'click-on' fluorogenic dyes.
| S-EPMC3010281 | biostudies-literature
Unknown Enhancing reactivity for bioorthogonal pretargeting by unmasking antibody-conjugated trans-cyclooctenes.
| S-EPMC5022565 | biostudies-literature
Unknown Developing visible fluorogenic 'click-on' dyes for cellular imaging.
| S-EPMC3178751 | biostudies-literature
Unknown Large-Scale Flow Photochemical Synthesis of Functionalized trans-Cyclooctenes Using Sulfonated Silica Gel.
| S-EPMC8224989 | biostudies-literature
Unknown Mechanism-Based Fluorogenic trans-Cyclooctene-Tetrazine Cycloaddition.
| S-EPMC5299526 | biostudies-literature
Unknown Synthesis of a fluorogenic cyclooctyne activated by Cu-free click chemistry.
| S-EPMC3219546 | biostudies-literature
Unknown Oligonucleotide labelling using a fluorogenic "click" reaction with a hemicarboxonium salt.
| S-EPMC6270631 | biostudies-literature
Unknown Genetically encoded tetrazine amino acid directs rapid site-specific in vivo bioorthogonal ligation with trans-cyclooctenes.
| S-EPMC3369569 | biostudies-literature