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An Optimized Protocol for the Synthesis of Peptides Containing trans-Cyclooctene and Bicyclononyne Dienophiles as Useful Multifunctional Bioorthogonal Probes
Chemistry - A European Journal 2021: Early View
Despite the great advances in solid-phase peptide synthesis (SPPS), the incorporation of certain functional groups into peptide sequences is restricted by the compatibility of the building blocks with conditions used during SPPS. In particular, the introduction of highly reactive groups used in modern bioorthogonal reactions into peptides remains elusive. Here, we present an optimized synthetic protocol enabling installation of two strained dienophiles, trans-cyclooctene (TCO) and bicyclononyne (BCN), into different peptide sequences. The two groups enable fast and modular post-synthetic functionalization of peptides, as we demonstrate in preparation of peptide-peptide and peptide-drug conjugates. Due to the excellent biocompatibility, the click-functionalization of the peptides can be performed directly in live cells. We further show that the introduction of both clickable groups into peptides enables construction of smart, multifunctional probes that can streamline complex chemical…
Non-Nucleotide RNA-Dependent RNA Polymerase Inhibitor That Blocks SARS-CoV-2 Replication
Viruses 13 (8): 1585 (2021)
α-Synuclein conformations followed by vibrational optical activity. Simulation and understanding of the spectra
Physical Chemistry Chemical Physics 23 (31): 16635-16645 (2021)
Polyhalogenated Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acids
Journal of Organic Chemistry 86 (15): 10303–10319 (2021)
Analyzing Discrepancies in Chemical-Shift Predictions of Solid Pyridinium Fumarates
Molecules 26 (13): 3857 (2021)