Late‐stage C−H Functionalization of Tryptophan‐Containing Peptides with Thianthrenium Salts: Conjugation and Ligation

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 62(9)

Published: Dec. 30, 2022

Abstract Bioorthogonal late‐stage diversification of structurally complex peptides bears enormous potential for drug discovery and molecular imaging, among other applications. Herein, we report on a palladium‐catalyzed C−H arylation tryptophan‐containing with readily accessible modular arylthianthrenium salts. Under exceedingly mild reaction conditions, the was accomplished. The tunability ease preparation salts allowed expedient stitching drug, natural product, peptidic scaffolds by forging sterically congested biaryl linkages. robustness palladium catalysis regime reflected full tolerance plethora sensitive coordinating functional groups. Hence, our manifold enabled efficient access to highly decorated, labelled, conjugated, ligated linear cyclic peptides.

Language: Английский

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Manganese-Catalyzed Electrochemical Oxidation of Tryptophan-Containing Peptides and Indole Derivatives by O₂

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 3928 - 3939

Published: Feb. 20, 2025

Language: Английский

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Late-stage peptide labeling with near-infrared fluorogenic nitrobenzodiazoles by manganese-catalyzed C–H activation

Chemical Science, Journal Year: 2023, Volume and Issue: 14(21), P. 5728 - 5733

Published: Jan. 1, 2023

Late-stage diversification of structurally complex amino acids and peptides provides tremendous potential for drug discovery molecular imaging. Specifically, labeling with fluorescent tags is one the most important methods visualizing their mode operation. Despite major recent advances in field, direct peptide by C-H activation largely limited to dyes relatively short emission wavelengths, leading high background signals poor signal-to-noise ratios. In sharp contrast, here we report on catalyzed non-toxic manganese(i) via C(sp2)-H alkenylation chemo- site-selective manners, providing modular access novel near-infrared (NIR) nitrobenzodiazole-based fluorogenic probes.

Language: Английский

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Backbone-Enabled and Ester Groups Switched δ-C(sp²)–H Amination/Fluorination: Cyclic Dipeptides Synthesis

Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5130 - 5135

Published: June 6, 2024

An efficient and concise strategy for the synthesis of cyclic dipeptides via Pd-catalyzed site-selective δ-C(sp2)–H amination/fluorination N-to-C cyclization is disclosed. The backbone amides within serves as endogenous directing groups, while desired products were switched by C-terminal ester group. This chemistry presents a novel robust alternative to construct cyclodipeptide fragments.

Language: Английский

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Application of the Palladium/Norbornene Cooperative Catalysis to Synthesis of Natural Products and Materials

Published: Feb. 28, 2025

Language: Английский

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Pd( II )‐Initiated Palladium/Norbornene Cooperative Catalysis

Published: Feb. 28, 2025

Language: Английский

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The application of C–H bond functionalization in the total syntheses of indole natural products

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 9(4), P. 1195 - 1210

Published: Dec. 13, 2021

The recent advances in total synthesis of indole natural products focusing on the application C–H bond functionalization are summarized.

Language: Английский

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Concise Synthesis of 2,5-Diketopiperazines via Catalytic Hydroxy-Directed Peptide Bond Formations

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 6901 - 6910

Published: May 1, 2023

2,5-Diketopiperazines (DKPs) with hydroxymethyl functional groups are essential structures found in many bioactive molecules and materials. We have established a simple protocol for the concise synthesis of this type DKPs through diboronic acid anhydride-catalyzed hydroxy-directed peptide bond formations. The sequential reactions report, which consist three steps, an intermolecular catalytic condensation reaction water is only byproduct, deprotection nitrogen-protecting group, intramolecular cyclization, enabled functionalized high to excellent yields without any intermediate purification. utility has been demonstrated by synthesizing natural products, phomamide Cyclo(Deala-l-Leu).

Language: Английский

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The recent advances in cobalt-catalyzed C(sp³)–H functionalization reactions

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 21(4), P. 673 - 699

Published: Dec. 22, 2022

Over the past decades, reactions involving C-H functionalization have become a hot theme in organic transformations because they lot of potential for streamlined synthesis complex molecules. C(sp3)-H bonds are present most species. Since molecules massive significance various aspects life, exploitation and hold enormous importance. In recent years, first-row transition metal-catalyzed direct selective has emerged as simple environmentally friendly synthetic method due to its low cost, unique reactivity profiles easy availability. Therefore, research advancements being made conceive catalytic systems that foster under benign reaction conditions. Cobalt-based catalysts offer mild convenient conditions at reasonable expense compared conventional 2nd 3rd-row metal catalysts. Consequently, probing Co-based is one topics from outlook an chemist. This review primarily focuses on literature 2018 2022 sheds light substrate scope, selectivity, benefits limitations cobalt transformations.

Language: Английский

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Visible‐Light‐Induced Oxidative Carboazidation of Arylacrylamides

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(6), P. 860 - 864

Published: Feb. 23, 2023

A visible-light-induced oxidative carboazidation of arylacrylamides by cascade C−N and C−C bond-forming strategy is reported. Various functional groups are tolerated to afford the desired azide oxindoles in 22–86% yields under standard conditions. Mechanistic studies demonstrate that reaction proceeded via a radical pathway. As service our authors readers, this journal provides supporting information supplied authors. Such materials peer reviewed may be re-organized for online delivery, but not copy-edited or typeset. Technical support issues arising from (other than missing files) should addressed Please note: The publisher responsible content functionality any Any queries content) directed corresponding author article.

Language: Английский

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