Design and Synthesis of Aza-Bicyclononene Dienophiles for Rapid Fluorogenic Ligations
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F18%3A00489643" target="_blank" >RIV/61388963:_____/18:00489643 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/chem.201705188" target="_blank" >http://dx.doi.org/10.1002/chem.201705188</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/chem.201705188" target="_blank" >10.1002/chem.201705188</a>
Alternative languages
Result language
angličtina
Original language name
Design and Synthesis of Aza-Bicyclononene Dienophiles for Rapid Fluorogenic Ligations
Original language description
Fluorogenic bioorthogonal reactions enable visualization of biomolecules under native conditions with excellent signal-to-noise ratio. Here, we present the design and synthesis of conformationally-strained aziridine-fused trans-cyclooctene (aza-TCO) dienophiles, which lead to the formation of fluorescent products in tetrazine ligations without the need for attachment of an extra fluorophore moiety. The presented aza-TCOs adopt the highly strained “half-chair” conformation, which was predicted computationally and confirmed by NMR measurements and X-ray crystallography. Kinetic studies revealed that the aza-TCOs belong to the most reactive dienophiles known to date. The potential of the newly developed aza-TCO probes for bioimaging applications is demonstrated by protein labeling experiments, imaging of cellular glycoconjugates and peptidoglycan imaging of live bacteria.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Chemistry - A European Journal
ISSN
0947-6539
e-ISSN
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Volume of the periodical
24
Issue of the periodical within the volume
10
Country of publishing house
DE - GERMANY
Number of pages
7
Pages from-to
2426-2432
UT code for WoS article
000425381200021
EID of the result in the Scopus database
2-s2.0-85041021612