Rapid reaction rate is an important feature of strain promoted azide-alkyne cycloadditions (SPAAC) for use in bioorthogonal chemistry. The ability to control polarization of strained cycloalkynes is a known strategy in enhancing reaction rate, as well as chemoselectivity of SPAAC reactions. A class of heterocyclic cyclooctyne containing sulfamate backbone (SNO-OCTs) have been previously reported to have favorable orbital interactions which enhances reaction rate. A new SNO-OCT derivative employing a difluoro moiety at the propargylic position outpaces strain activated cycloalkynes such as bicyclo[6.1.0]nonyne (BCN) and dibenzoazacyclooctyne (DIBAC), some of the fastest cyclooctynes to date. Different derivatives of SNO-OCT can be employed simultaneously with diazoacetamide and tetrazine with good mutual orthogonality. The ability to achieve mutual orthogonality by tuning the electronics of cycloalkyne has great potential for application in chemistry and biology.<br/>

Orthogonal biolabeling using modified SNO- OCTs with tunable alkyne polarizability

2019 Spring National Meeting

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