Journal
ORGANIC LETTERS
Volume 25, Issue 49, Pages 8792-8796Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c03250
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A heterobifunctional cross-linker with orthogonal reactivity towards thiol and amine was designed and synthesized for constructing stapled peptides of different sizes and functionalizing proteins with mono- or dual modifications.
A heterobifunctional cross-linker with one sulfhydryl-reactive dinitroimidazole end and another amine-reactive N-hydroxysuccinimide (NHS) ester end was designed and synthesized. The two motifs of this cross-linker, dinitroimidazole and NHS ester, proved to react with thiol and amine, respectively, in an orthogonal way. The cross-linker was further applied to construct stapled peptides of different sizes and mono- and dual functionalization (including biotinylation, PEGylation, and fluorescence labeling) of protein.
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