4.8 Review

Photoinduced C(sp3)-H Functionalization of Glycine Derivatives: Preparation of Unnatural α-Amino Acids and Late-Stage Modification of Peptides

Related references

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

Copper-catalyzed asymmetric C(sp3)-H cyanoalkylation of glycine derivatives and peptides

Rupeng Qi et al.

Summary: In this study, a copper-catalyzed asymmetric cyanoalkylation of C(sp(3))-H was reported, allowing for efficient incorporation of cyanoalkyl groups into amino acids and peptides with high yields and excellent stereoselectivities. The reaction is significant for peptide synthesis and drug discovery.

NATURE COMMUNICATIONS (2023)

Article Chemistry, Multidisciplinary

Glycosyl Radical-Based Synthesis of C-Glycoamino Acids and C-Glycopeptides

Chao Wang et al.

Summary: This article summarizes the important application of radical-based reactions in glycosylation modifications, focusing on the synthesis of unnatural amino acids and the late-stage modification of peptides and proteins. It also provides an outlook on the future development in this direction.

CHEMISTRY-A EUROPEAN JOURNAL (2023)

Review Chemistry, Multidisciplinary

Copper-catalyzed radical relay in C(sp3)-H functionalization

Zuxiao Zhang et al.

Summary: Radical-involved transition metal catalysis enables new reactivities, and copper-catalyzed radical relay shows great potential in C(sp(3))-H functionalization. Significant progress has been made in asymmetric C-H functionalization through ligand design.

CHEMICAL SOCIETY REVIEWS (2022)

Article Chemistry, Multidisciplinary

Visible-Light-Promoted Stereoselective C(sp3)-H Glycosylation for the Synthesis of C-Glycoamino Acids and C-Glycopeptides

Rupeng Qi et al.

Summary: Visible-light-promoted and Cu-catalyzed stereoselective C-glycosylation allows for mild reaction conditions compatible with various carbohydrate substrates, leading to the synthesis of a wide variety of C-glycoamino acids and C-glycopeptidomimetics with good yields and excellent stereoselectivities. Dual-functional photocatalyst formed in situ plays a key role in catalyzing the photoredox process and controlling the stereoselectivity of the glycosylation reaction.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Organic

Visible-Light-Induced Copper-Catalyzed Asymmetric C(sp3)-C(sp3)-H Glycosylation: Access to C-Glycopeptides

Ya-Nan Ding et al.

Summary: In this study, a practical and highly efficient method for visible-light-induced copper-catalyzed N-aminoquinoline-directed asymmetric C(sp(3))-C(sp(3))-H glycosylation was reported. Additionally, C-glycopeptides were synthesized through the glycosylation of nondeoxysugars with amino acids. This research provides a new approach for the synthesis of C-glycopeptides and C-glycoamino acids.

ORGANIC LETTERS (2022)

Review Chemistry, Organic

Radical-Mediated C-H Alkylation of Glycine Derivatives: A Straightforward Strategy for Diverse α-Unnatural Amino Acids

Madala Hari Babu et al.

Summary: The radical-based alpha-C-H alkylation method plays an important role in synthesizing unnatural amino acids, especially in glycine derivatives. This method provides a pathway for accessing a variety of complex alpha-unnatural amino acids and is a valuable variant.

EUROPEAN 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)

Review Chemistry, Multidisciplinary

Photoactive Copper Complexes: Properties and Applications

Jerome Beaudelot et al.

Summary: Photocatalyzed and photosensitized chemical processes, particularly using photoactive copper(I) complexes, have gained significant attention and application in various fields. This review provides a comprehensive overview of the structural, photophysical, and electrochemical properties of mononuclear copper(I) complexes, highlighting critical structural parameters and their impact on the properties. It also explores the main areas of application for these complexes, such as photoredox catalysis, hydrogen production, photoreduction of carbon dioxide, and dye-sensitized solar cells.

CHEMICAL REVIEWS (2022)

Article Chemistry, Organic

Construction of Peptide Macrocycles via Radical-Mediated Intramolecular C-H Alkylations

Xiafei Hu et al.

Summary: New methods have been developed in this study to construct peptide macrocycles via radical-mediated intramolecular C-H alkylation reactions under photoredox catalysis, providing a new strategy for the synthesis of complex peptide macrocycles.

ORGANIC LETTERS (2021)

Article Chemistry, Physical

Copper-Catalyzed Asymmetric Deconstructive Alkynylation of Cyclic Oximes

Hang-Dong Zuo et al.

Summary: A general asymmetric deconstructive alkynylation of cyclic oximes with terminal alkynes was reported using copper/chiral cinchona alkaloid-based N,N,P-ligand catalysts, leading to the production of more than 60 examples of enantioenriched gamma- and delta-alkynyl nitriles. The resulting chiral alkynyl nitriles are intermediates that can be converted into various skeletally diverse chiral molecules, including delta-alkynyl amides, epsilon-alkenyl carbamate, and zeta-keto nitrile, under suitable reaction conditions.

ACS CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Visible Light Induced Cu-Catalyzed Asymmetric C(sp3)-H Alkylation

Rupeng Qi et al.

Summary: Asymmetric functionalization of C-H is a attractive strategy in asymmetric synthesis, and photoredox catalysis has emerged as an efficient way to synthesize organic compounds under mild conditions.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (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, Multidisciplinary

Visible-light promoted α-alkylation of glycine derivatives with alkyl boronic acids

Jiayuan Wang et al.

Summary: This method utilizes a visible-light-mediated aerobic alpha-alkylation reaction of glycine derivatives with alkyl boronic acids in the presence of a Ru/Cu catalyst system to efficiently produce a wide range of complex unnatural alpha-amino-acid derivatives. It features mild reaction conditions and broad substrate scope.

CHEMICAL COMMUNICATIONS (2021)

Review Chemistry, Multidisciplinary

Photocatalytic methods for amino acid modification

Thomas A. King et al.

Summary: Amino acid modification is crucial in various fields, and photocatalysis has emerged as a mild approach capable of modifying almost all canonical amino acids, enhancing its usefulness significantly. This method has wide potential applications and can function under physiological conditions.

CHEMICAL SOCIETY REVIEWS (2021)

Review Chemistry, Medicinal

Design and synthesis of glycomimetics: Recent advances

Alice Tamburrini et al.

MEDICINAL RESEARCH REVIEWS (2020)

Review Chemistry, Multidisciplinary

Synthetic Methods Driven by the Photoactivity of Electron Donor-Acceptor Complexes

Giacomo E. M. Crisenza et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Protein-Protein Cross-Coupling via Palladium-Protein Oxidative Addition Complexes from Cysteine Residues

Heemal H. Dhanjee et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Catalyst-Free Deaminative Functionalizations of Primary Amines by Photoinduced Single-Electron Transfer

Jingjing Wu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Visible-Light-Mediated Charge Transfer Enables C-C Bond Formation with Traceless Acceptor Groups

Michael J. James et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Article Multidisciplinary Sciences

Elucidating the active δ-opioid receptor crystal structure with peptide and small-molecule agonists

Tobias Claff et al.

SCIENCE ADVANCES (2019)

Article Chemistry, Medicinal

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

Antoine Henninot et al.

JOURNAL OF MEDICINAL CHEMISTRY (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

Transition-metal-catalyzed C-H functionalization for late-stage modification of peptides and proteins

Xi Lu et al.

CHINESE CHEMICAL LETTERS (2018)

Article Chemistry, Multidisciplinary

Scalable thioarylation of unprotected peptides and biomolecules under Ni/photoredox catalysis

Brandon A. Vara et al.

CHEMICAL SCIENCE (2018)

Review Chemistry, Multidisciplinary

Copper-Catalyzed Radical Relay for Asymmetric Radical Transformations

Fei Wang et al.

ACCOUNTS OF CHEMICAL RESEARCH (2018)

Article Chemistry, Multidisciplinary

Visible-Light-Driven, Copper-Catalyzed Decarboxylative C(sp(3))-H Alkylation of Glycine and Peptides

Chao Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Photoinduced, Copper-Catalyzed Decarboxylative C-N Coupling to Generate Protected Amines: An Alternative to the Curtius Rearrangement

Wei Zhao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Multidisciplinary Sciences

Selective sp3 C-H alkylation via polarity-match-based cross-coupling

Chip Le et al.

NATURE (2017)

Article Chemistry, Organic

Co-Catalyzed C(sp3)-H Oxidative Coupling of Glycine and Peptide Derivatives

Marcos San Segundo et al.

ORGANIC LETTERS (2017)

Article Chemistry, Multidisciplinary

Visible-Light-Driven Palladium-Catalyzed Radical Alkylation of C-H Bonds with Unactivated Alkyl Bromides

Wen-Jun Zhou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

Applications of Nonenzymatic Catalysts to the Alteration of Natural Products

Christopher R. Shugrue et al.

CHEMICAL REVIEWS (2017)

Article Biochemistry & Molecular Biology

Residue-Specific Peptide Modification: A Chemist's Guide

Justine N. deGruyter et al.

BIOCHEMISTRY (2017)

Review Chemistry, Organic

Radical Cation Salts: From Single-Electron Oxidation to C-H Activation

Xiaodong Jia

SYNTHESIS-STUTTGART (2016)

Review Chemistry, Multidisciplinary

Electroreductive Remediation of Halogenated Environmental Pollutants

Erin T. Martin et al.

CHEMICAL REVIEWS (2016)

Review Chemistry, Multidisciplinary

Expanding the chemical toolbox for the synthesis of large and uniquely modified proteins

Somasekhar Bondalapati et al.

NATURE CHEMISTRY (2016)

Article Multidisciplinary Sciences

Asymmetric copper-catalyzed C-N cross-couplings induced by visible light

Quirin M. Kainz et al.

SCIENCE (2016)

Article Chemistry, Multidisciplinary

Glycosylation, an effective synthetic strategy to improve the bioavailability of therapeutic peptides

Shayli Varasteh Moradi et al.

CHEMICAL SCIENCE (2016)

Article Chemistry, Multidisciplinary

Enantioselective synthesis of arylglycine derivatives by direct C-H oxidative cross-coupling

Xiao-Hong Wei et al.

CHEMICAL COMMUNICATIONS (2015)

Review Chemistry, Multidisciplinary

Advances in Chemical Protein Modification

Omar Boutureira et al.

CHEMICAL REVIEWS (2015)

Article Chemistry, Multidisciplinary

Photo-induced Metal-Catalyst-Free Aromatic Finkelstein Reaction

Lu Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Review Chemistry, Multidisciplinary

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

Anais F. M. Noisier et al.

CHEMICAL REVIEWS (2014)

Review Chemistry, Multidisciplinary

Transition-Metal-Free Coupling Reactions

Chang-Liang Sun et al.

CHEMICAL REVIEWS (2014)

Review Chemistry, Multidisciplinary

Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis

Christopher K. Prier et al.

CHEMICAL REVIEWS (2013)

Article Chemistry, Inorganic & Nuclear

Structural and biological implications of the binding of Leu-enkephalin and its metal derivatives to opioid receptors

Florian Wieberneit et al.

DALTON TRANSACTIONS (2013)

Article Chemistry, Medicinal

Development of Potent μ and δ Opioid Agonists with High Lipophilicity

Yeon Sun Lee et al.

JOURNAL OF MEDICINAL CHEMISTRY (2011)

Article Chemistry, Multidisciplinary

Cross-Dehydrogenative Coupling Reactions by Transition-Metal and Aminocatalysis for the Synthesis of Amino Acid Derivatives

Jin Xie et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

Article Biochemistry & Molecular Biology

Studies of protein-protein interfaces: A statistical analysis of the hydrophobic effect

Chung-Jung Tsai et al.

PROTEIN SCIENCE (2010)

Review Chemistry, Multidisciplinary

Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality

Ellen M. Sletten et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Article Multidisciplinary Sciences

Site-specific C-functionalization of free-(NH) peptides and glycine derivatives via direct C-H bond functionalization

Liang Zhao et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2009)

Review Chemistry, Multidisciplinary

Fresh look at electron-transfer mechanisms via the donor/acceptor bindings in the critical encounter complex

Sergiy V. Rosokha et al.

ACCOUNTS OF CHEMICAL RESEARCH (2008)

Article Chemistry, Multidisciplinary

Functionalizing glycine derivatives by direct C-C bond formation

Liang Zhao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

Review Multidisciplinary Sciences

Synthesis and medical applications of oligosaccharides

Peter H. Seeberger et al.

NATURE (2007)

Article Biochemical Research Methods

Efficient incorporation of unnatural amino acids into proteins in Escherichia coli

YH Ryu et al.

NATURE METHODS (2006)

Review Chemistry, Multidisciplinary

Protein posttranslational modifications: The chemistry of proteome diversifications

CT Walsh et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)