Bioorthogonal prodrug activation driven by a strain-promoted 1,3-dipolar cycloaddition† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c4sc02574a

Bioorthogonal prodrug activation driven by a strain-promoted 1,3-dipolar cycloaddition.

Due to the formation of hydrolysis-susceptible adducts, the 1,3-dipolar cycloaddition between an azide and strained trans-cyclooctene (TCO) has been disregarded in the field of bioorthogonal chemistry. We report a method which uses the instability of the adducts to our advantage in a prodrug activation strategy. The reaction of trans-cyclooctenol (TCO-OH) with a model prodrug resulted in a rapi...

Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides† †Electronic supplementary information (ESI) available: Detailed experimental procedures, and spectral data for all compounds, including scanned images of 1H and 13C NMR spectra. CCDC 1019046. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4sc02612h

Methyltransferase-directed covalent coupling of fluorophores to DNA† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc04229e Click here for additional data file.

We report an assay for determining the number of fluorophores conjugated to single plasmid DNA molecules and apply this to compare the efficiency of fluorophore coupling strategies for covalent DNA labelling. We compare a copper-catalyzed azide-alkyne cycloaddition reaction, amine to N-hydroxysuccinimidyl ester coupling reaction and strain-promoted azide-alkyne cycloaddition reaction for fluore...

Catalytic [2 + 2 + 2] cycloaddition with indium(iii)-activated formaldimines: a practical and selective access to hexahydropyrimidines and 1,3-diamines from alkenes† †Electronic supplementary information (ESI) available. CCDC 1538722 and 1554489. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc02576a Click here for additional data file. Click here for additional data file.

Catalysis of a 1,3-dipolar reaction by distorted DNA incorporating a heterobimetallic platinum(ii) and copper(ii) complex† †Electronic supplementary information (ESI) available: Experimental details, characterization of cycloadducts and intermediates, computational data. CCDC 1411372 and 1411373. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc02311a