This work provides a reference for choosing appropriate cyclooctyne to couple with azides and can be useful for the design of biosensors or bio‐platforms for analyte detection, cell capture, and other biological applications. Both cyclooctynes demonstrate reliable binding performance with azide‐bearing diblock polymer brushes via μCS, but DBCO shows a higher surface density of molecular immobilization according to the protein binding assays. The assessment of binding efficiency is conducted on ordered arrays spotted by microchannel cantilever spotting (μCS) with a normal fluorescent microscope.
The polymer brushes are composed of an antifouling bottom block and azide‐terminated top block. In the present work, different derivatives of dibenzocyclooctyne/bicyclononyne (DBCO/BCN) linked to either a fluorophore or a biotin‐moiety are patterned on ultra‐low fouling polymer brushes, which can avoid unspecific protein contamination without any prior blocking steps. While numerous studies have focused on enhancing the reactivity of cyclooctynes, a facile method to evaluate the binding efficiency for cyclooctyne‐azide‐based immobilization without any sophisticated facilities is still missing.
Strain‐promoted alkyne‐azide cycloaddition (SPAAC) has become an indispensable tool in bioorthogonal conjugation and surface immobilization. The obtained results will help in obtaining a better understanding of the factors that affect the relative cycloaddition rates of norbornenes with tetrazines, which are crucial for selectively tuning their efficacy. The theoretical predictions were confirmed with the experimental data and analyzed with the use of the distortion/interaction model.
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The inverse electron-demand Diels Alder reaction of 3,6-dipyridin-2-yl-1,2,4,5-tetrazine with a series of norbornene derivatives was studied with quantum mechanical calculations at the M06-2X/6-311+G(d,p) level of theory. Among the different types of dienophiles used in the IEDDA reactions, norbornenes have been widely used given their high stability and fast reaction rates. In this regard, the inverse electron demand Diels-Alder (IEDDA) reaction represents a promising metal-free alternative with enhanced reaction rates compared to other reactions of the click chemistry toolbox. The study of the reaction rates and mechanism of click chemistry reactions still remains an interesting challenge in organic chemistry.
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