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Site-Selective Synthesis of Insulin Azides and Bioconjugates

Sobhana Babu Boga, Shane W Krska, Songnian Lin, Dmitri Pissarnitski, Lin Yan, Ahmet Kekec, Weijuan Tang, Nicholas A Pierson, Christopher A Strulson, Eric Streckfuss, Xiaohong Zhu, Xiaoping Zhang, Terri Kelly, Craig A Parish
Bioconjugate Chemistry 2019 April 4
A synthetic method to access novel azido-insulin analogs directly from recombinant human insulin (RHI) was developed via diazo-transfer chemistry using imidazole-1-sulfonyl azide. Systematic optimization of reaction conditions led to site-selective azidation of amino acids B1-phenylalanine and B29-lysine present in RHI. Subsequently, the azido-insulin analogs were used in azide-alkyne [3 + 2] cycloaddition reactions to synthesize a diverse array of triazole-based RHI bioconjugates that were found to be potent human insulin receptor binders. The utility of this method was further demonstrated by the concise and controlled synthesis of a heterotrisubstituted insulin conjugate.


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