AI Article Synopsis
- * It details a novel Pd-catalyzed reaction that specifically targets tyrosine (Tyr) residues in peptides using a removable silanol protecting group, showcasing high selectivity.
- * The method is versatile, applicable to various hexapeptides and supports different olefins, expanding options for late-stage peptide modifications and introducing new protection strategies for Tyr in solid-phase peptide synthesis (SPPS).
Article Abstract
Chemical modification of a specific amino acid residue on peptides represents an efficient strategy to improve their pharmacokinetics and facilitates the potential to achieve post-synthetic diversification of peptides. Herein, we reported the first Pd-catalyzed late-stage -olefination of Tyr residues on peptides with high chemo- and site-selectivity, by employing the easily attached and removable silanol as a bifunctional protecting group and directing group. Up to hexapeptides with variation on amino acid sequences or locations of the Tyr residue and different olefins were compatible with this protocol, which enriched the chemical toolbox for late-stage modification C(sp)-H functionalization. Furthermore, the orthogonal protection strategies of Tyr were also developed and could be applied to SPPS.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8159358 | PMC |
| http://dx.doi.org/10.1039/d0sc02439b | DOI Listing |
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Article Synopsis
- * It details a novel Pd-catalyzed reaction that specifically targets tyrosine (Tyr) residues in peptides using a removable silanol protecting group, showcasing high selectivity.
- * The method is versatile, applicable to various hexapeptides and supports different olefins, expanding options for late-stage peptide modifications and introducing new protection strategies for Tyr in solid-phase peptide synthesis (SPPS).
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