2023
DOI: 10.1021/jacs.3c10792
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Side-Selective Solid-Phase Metallaphotoredox N(in)-Arylation of Peptides

José A. C. Delgado,
Ya-Ming Tian,
Michela Marcon
et al.

Abstract: Postsynthetic diversification of peptides through selective modification of endogenous amino acid side chains has enabled significant advances in peptide drug discovery while expanding the biological and medical chemistry space. However, current tools have been focused on the modification of reactive polar and ionizable side chains, whereas the decoration of aromatic systems (e.g., the N (in) of the tryptophan) has been a long-standing challenge. Here, we introduce metallaphotocatalysis in solid-phase peptide … Show more

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Cited by 6 publications
(1 citation statement)
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“… 40 More recently, Paixão and coworkers have disclosed the dual photoredox/metal catalysis mediated N (in) -arylation of tryptophan-containing peptide on resin. 41 Our group has developed a chiral phosphoric acid-catalyzed chemospecific enantioselective functionalization of tryptophan at the N1 position, enabling direct access to chiral propargyl aminal derivatives with good yields and stereoselectivities. 42 Studer and coworker have reported the visible-light-mediated N1 position hemiaminal modification of Trp-containing peptides through the N–H insertion of siloxycarbenes photochemically generated from acylsilanes.…”
Section: Introductionmentioning
confidence: 99%
“… 40 More recently, Paixão and coworkers have disclosed the dual photoredox/metal catalysis mediated N (in) -arylation of tryptophan-containing peptide on resin. 41 Our group has developed a chiral phosphoric acid-catalyzed chemospecific enantioselective functionalization of tryptophan at the N1 position, enabling direct access to chiral propargyl aminal derivatives with good yields and stereoselectivities. 42 Studer and coworker have reported the visible-light-mediated N1 position hemiaminal modification of Trp-containing peptides through the N–H insertion of siloxycarbenes photochemically generated from acylsilanes.…”
Section: Introductionmentioning
confidence: 99%