Selective strain-promoted azide-alkyne cycloadditions through transient protection of bicyclo[6.1.0]nonynes with silver or gold
Complexation of bicyclo[6.1.0]nonynes with a cationic silver or gold salt results in protection from a click reaction with azides. The cycloalkyne protection using the silver or gold salt enables selective strain-promoted azide-alkyne cycloadditions of di
Facile assembly of three cycloalkyne-modules onto a platform compound bearing thiophene: S, S -dioxide moiety and two azido groups
An efficient method to assemble three cycloalkyne-modules onto a platform compound bearing a thiophene S,S-dioxide moiety and two azido groups has been developed. The sequential reactions without catalysis or additives enabled the facile preparation of trifunctional molecules by a simple procedure. One-pot assembly was also achieved using the platform and three cycloalkynes.
Convergent synthesis of trifunctional molecules by three sequential azido-type-selective cycloadditions
A facile strategy for the synthesis of trifunctional molecules involving three sequential selective triazole-forming reactions is proposed. This method exploits three kinds of mechanistically different azido-type-selective cycloadditions. Three different azidophiles could be efficiently connected to a triazido platform molecule with three types of azido groups in a consecutive manner, which rendered a practical trifunctional molecule readily available.
Staudinger reaction using 2,6-dichlorophenyl azide derivatives for robust aza-ylide formation applicable to bioconjugation in living cells
Efficient formation of water- and air-stable aza-ylides has been achieved using the Staudinger reaction between electron-deficient aromatic azides such as 2,6-dichlorophenyl azide and triarylphosphines. The reaction proceeds rapidly and has been successfully applied to chemical modification of proteins in living cells.
Meguro, Tomohiro,Terashima, Norikazu,Ito, Harumi,Koike, Yuka,Kii, Isao,Yoshida, Suguru,Hosoya, Takamitsu
supporting information
p. 7904 - 7907
(2018/07/25)
A bioorthogonal ligation enabled by click cycloaddition of o-quinolinone quinone methide and vinyl thioether
There is an increasing interest in the use of bioorthogonal ligation to advance biomedical research through selective labeling of biomolecules in living systems. Accordingly, discovering new reactions to expand the toolbox of bioorthogonal chemistry is of particular interest to chemical biologists. Herein we report a new bioorthogonal ligation enabled by click hetero-Diels-Alder (HDA) cycloaddition of in situ-generated o-quinolinone quinone methides and vinyl thioethers. This reaction is highly selective and proceeds smoothly under aqueous conditions. The functionalized vinyl thioethers are small and chemically stable in vivo, making them suitable for use as bioorthogonal chemical reporters that can be effectively coupled to various biomolecules. We utilized this bioorthogonal ligation for site-specific labeling of proteins as well as imaging of bioactive small molecules inside live cells.
Li, Qiang,Dong, Ting,Liu, Xiaohui,Lei, Xiaoguang
supporting information
p. 4996 - 4999
(2013/05/22)
Nitrones as dipoles for rapid strain-promoted 1,3-dipolar cycloadditions with cyclooctynes
Strain-promoted cycloadditions of nitrones with cyclooctynes (k2 = 1.5 M-1 s-1 at 25 °C) are up to 25 times more rapid than comparable reactions of azides. The Royal Society of Chemistry 2010.
McKay, Craig S.,Moran, Joseph,Pezacki, John Paul
supporting information; experimental part
p. 931 - 933
(2010/06/12)
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