4.8 Article

Metal-Free Late-Stage Alkylation of Tryptophan and Tryptophan-Containing Peptides with 1,3-Dithiane Derivatives

Related references

Note: Only part of the references are listed.
Article Chemistry, Multidisciplinary

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

Nikolaos Kaplaneris et al.

Summary: We achieved the late-stage diversification of structurally complex peptides through palladium-catalyzed C-H arylation. The tunability and ease of preparation of arylthianthrenium salts allowed us to forge sterically congested biaryl linkages between tryptophan-containing peptides and drug, natural product, and peptidic scaffolds. The robustness of the palladium catalysis regime was demonstrated by the full tolerance of sensitive and coordinating functional groups. As a result, we efficiently accessed highly decorated, labelled, conjugated, and ligated linear and cyclic peptides.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Article Chemistry, Multidisciplinary

PIII-Directed Late-Stage Ligation and Macrocyclization of Peptides with Olefins by Rhodium Catalysis

Lei Liu et al.

Summary: We report a method for late-stage peptide ligation and macrocyclization through rhodium-catalyzed alkylation of tryptophan residues at the C7 position. This study demonstrates site-selective peptide C-H alkylation through deconjugative isomerization using internal olefins. Our method provides access to peptide macrocycles with unique Trp(C7)-alkyl crosslinks and exhibits potent cytotoxicity towards cancer cells.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Organic

Molecular Iodine-Catalysed Reductive Alkylation of Indoles: Late-Stage Diversification for Bioactive Molecules

Xionglve Cheng et al.

Summary: In this study, a molecular iodine-catalysed reductive alkylation reaction of indoles with carbonyl compounds was reported for the efficient synthesis of C3-alkylated indoles. This metal-free and environmentally friendly process showed excellent functional group tolerance, mild reaction conditions, and a wide range of substrates. Importantly, the synthetic usefulness of this strategy in pharmacology was demonstrated through the late-stage modification of drug-like molecules.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Organic

One-Pot Sequential Synthesis of 3,3′- or 2,3′-Bis(indolyl)methanes by Using 1,3-Dithiane as the Methylene Source

Kang Dong et al.

Summary: A simple and efficient method for synthesizing structurally diverse symmetrical and unsymmetrical 3,3'- and 2,3'-bisindolylmethanes has been developed using a one-pot sequential reaction with 1,3-dithiane as the methylene source. The important AhR agonists ICZ and malassezin were successfully synthesized with excellent efficiency using this straightforward approach.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Organic

C(sp3)-H/C(sp3)-H Dehydrogenative Radical Coupling of Glycine Derivatives

Jiayuan Wang et al.

Summary: A general C(sp3)-H/C(sp3)-H dehydrogenative coupling strategy for the preparation of various natural or unnatural amino acids from readily available glycine derivatives and hydrocarbons is reported, which involves a combination of SET and HAT process.

ORGANIC LETTERS (2022)

Article Biotechnology & Applied Microbiology

Trends in peptide drug discovery

Markus Muttenthaler et al.

Summary: This Perspective summarizes key trends in peptide drug discovery and development, including human hormones, elegant medicinal chemistry and rational design strategies, peptide drugs derived from nature, and major breakthroughs in molecular biology and peptide chemistry. It also emphasizes lessons from earlier approaches that are still relevant today and discusses emerging strategies impact on peptide drug discovery.

NATURE REVIEWS DRUG DISCOVERY (2021)

Article Chemistry, Organic

A Metal-Free Reductive N-Alkylation of Indoles with Aldehydes

Nicholas A. Clanton et al.

Summary: A metal-free method has been developed for the reductive N-alkylation of indoles using aldehydes and inexpensive Et3SiH as the reductant. A wide range of aromatic and aliphatic aldehydes, as well as various substituted indoles, are viable substrates. The method was successfully demonstrated on a 100 mmol scale for a one-pot sequential 1, 3-alkylation of a substituted indole.

ORGANIC LETTERS (2021)

Review Biochemistry & Molecular Biology

Recent Advances in Late-Stage Construction of Stapled Peptides via C-H Activation

Jiang Liu et al.

Summary: The late-stage transition metal-catalyzed C-H activation method provides a way to increase the diversity of stapled peptides, attracting wide interest due to its robustness and applicability for peptide stapling. This review summarizes the methods for late-stage construction of stapled peptides via transition metal-catalyzed C-H activation.

CHEMBIOCHEM (2021)

Review Chemistry, Multidisciplinary

Postassembly Modifications of Peptides via Metal-Catalyzed C-H Functionalization

Hua-Rong Tong et al.

Summary: This review highlights the recent advancements in metal-catalyzed C-H functionalization (CHF) chemistry for postassembly modification of peptides and proteins. Various strategies targeting amino acid side chains, backbone, and terminus groups on peptides are discussed, along with brief comments on nonmetal-mediated approaches. Readers are provided with a comprehensive overview of the current state of CHF-enabled peptide modification.

CCS CHEMISTRY (2021)

Article Chemistry, Medicinal

Discovery of novel phosphatidylcholine-specific phospholipase C drug-like inhibitors as potential anticancer agents

Chatchakorn Eurtivong et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2020)

Article Multidisciplinary Sciences

A fluorogenic cyclic peptide for imaging and quantification of drug-induced apoptosis

Nicole D. Barth et al.

NATURE COMMUNICATIONS (2020)

Review Chemistry, Multidisciplinary

Late-stage functionalization of peptides via a palladium-catalyzed C(sp3)-H activation strategy

Bei-Bei Zhan et al.

CHEMICAL COMMUNICATIONS (2020)

Article Chemistry, Multidisciplinary

Construction of Natural-Product-Like Cyclophane-Braced Peptide Macrocycles via sp3 C-H Arylation

Bo Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Review Endocrinology & Metabolism

Tryptophan Metabolic Pathways and Brain Serotonergic Activity: A Comparative Review

Erik Hoglund et al.

FRONTIERS IN ENDOCRINOLOGY (2019)

Article Chemistry, Medicinal

Design of Trp-Rich Dodecapeptides with Broad-Spectrum Antimicrobial Potency and Membrane-Disruptive Mechanism

Yinfeng Lyu et al.

JOURNAL OF MEDICINAL CHEMISTRY (2019)

Article Multidisciplinary Sciences

Late-stage peptide C-H alkylation for bioorthogonal C-H activation featuring solid phase peptide synthesis

Alexandra Schischko et al.

NATURE COMMUNICATIONS (2019)

Article Chemistry, Multidisciplinary

Late-Stage Peptide Diversification through Cobalt-Catalyzed C-H Activation: Sequential Multicatalysis for Stapled Peptides

Melanie M. Lorion et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Pd-catalyzed site-selective C(sp2)-H radical acylation of phenylalanine containing peptides with aldehydes

Marcos San Segundo et al.

CHEMICAL SCIENCE (2019)

Article Chemistry, Medicinal

The Current State of Peptide Drug Discovery: Back to the Future?

Antoine Henninot et al.

JOURNAL OF MEDICINAL CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Site-Selective delta-C(sp(3))-H Alkylation of Amino Acids and Peptides with Maleimides via a Six-Membered Palladacycle

Bei-Bei Zhan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Review Chemistry, Multidisciplinary

Late-Stage Peptide Diversification by Position-Selective C-H Activation

Wei Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Chemoselective Peptide Modification via Photocatalytic Tryptophan β-Position Conjugation

Younong Yu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Review Chemistry, Multidisciplinary

Orally Active Peptides: Is There a Magic Bullet?

Andreas F. B. Raeder et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Stapled Peptides by Late-Stage C(sp3)-H Activation

Anais F. M. Noisier et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Bronsted Acid Catalysis in Visible-Light-Induced [2+2] Photocycloaddition Reactions of Enone Dithianes

Christoph Brenninger et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Manganese-Catalyzed C-H Alkynylation: Expedient Peptide Synthesis and Modification

Zhixiong Ruan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

Organometallic-Peptide Bioconjugates: Synthetic Strategies and Medicinal Applications

Bauke Albada et al.

CHEMICAL REVIEWS (2016)

Article Chemistry, Medicinal

Unusual Amino Acids in Medicinal Chemistry

Mark A. T. Blaskovich

JOURNAL OF MEDICINAL CHEMISTRY (2016)

Review Pharmacology & Pharmacy

Peptide therapeutics: current status and future directions

Keld Fosgerau et al.

DRUG DISCOVERY TODAY (2015)

Article Multidisciplinary Sciences

New peptide architectures through C-H activation stapling between tryptophan-phenylalanine/tyrosine residues

Lorena Mendive-Tapia et al.

NATURE COMMUNICATIONS (2015)

Review Chemistry, Multidisciplinary

C-H Functionalization in the Synthesis of Amino Acids and Peptides

Anais F. M. Noisier et al.

CHEMICAL REVIEWS (2014)

Article Chemistry, Multidisciplinary

Site-Selective C(sp3)-H Functionalization of Di-, Tr-, and Tetrapeptides at the N-Terminus

Wei Gong et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Review Biochemistry & Molecular Biology

The Future of Peptide-based Drugs

David J. Craik et al.

CHEMICAL BIOLOGY & DRUG DESIGN (2013)

Letter Chemistry, Medicinal

Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines

S Zhao et al.

JOURNAL OF MEDICINAL CHEMISTRY (2002)