Topics

Cu-Catalyzed Site-Selective C(sp)-H Radical Trifluoromethylation of Tryptophan-Containing Peptides.

07:00 EST 13th February 2020 | BioPortfolio

Summary of "Cu-Catalyzed Site-Selective C(sp)-H Radical Trifluoromethylation of Tryptophan-Containing Peptides."

Site-selective functionalization of C-H bonds within a peptide framework poses a challenging task of paramount synthetic relevance. Herein, we report an operationally simple C(sp)-H trifluoromethylation of tryptophan (Trp)-containing peptides. This fluorination technique is characterized by its chirality preservation, tolerance of functional groups, and scalability and exhibits chemoselectivity for Trp residues over other amino acid and heterocyclic units. As a result, it represents a sustainable tool toward the late-stage peptide modification and protein engineering.

Affiliation

Journal Details

This article was published in the following journal.

Name: Organic letters
ISSN: 1523-7052
Pages:

Links

DeepDyve research library

PubMed Articles [10800 Associated PubMed Articles listed on BioPortfolio]

18F-Trifluoromethanesulfinate enables Direct C-H 18F-Trifluoromethylation of Native Aromatic Residues in Peptides.

18F-Labeling strategies for unmodified peptides with [18F]fluoride require 18F-prosthetics for bioconjugation more often with cysteine thiols or lysine amines. Here, we explore selective radical chemi...

Aryl Sulfonium Salts for Site-selective Late-stage Trifluoromethylation.

Incorporation of the CF3 group into arenes has found increasing importance in drug discovery. Here we report the first photoredox-catalyzed cross-coupling of aryl thianthrenium salts with a copper-bas...

Oxazoline-/Copper-Catalyzed Alkoxyl Radical Generation: Solvent-Switched to Access 3a,3a'-Bisfuroindoline and 3-Alkoxyl Furoindoline.

We report the first example of oxazoline-/copper-catalyzed alcohol oxidation to generate the alkoxyl radical under additive-free conditions. The resulting alkoxyl radical addition to alkene enables us...

Biochemical and Mechanistic Characterization of the fungal reverse -1-Dimethylallyltryptophan Synthase DMATS1.

Dimethylallyltryptophan synthases catalyze the regiospecific transfer of (oligo)-prenylpyrophosphates to aromatic sub-strates like tryptophan derivatives. These reactions are key steps in many biosynt...

Site-Selective Functionalization of (sp3)C-H Bonds Catayzed by Artificial Metalloenzymes Containing an Iridium-Porphyrin Cofactor.

The selective functionalization of one C-H bond over others in nearly identical steric and electronic environments can facilitate the construction of complex molecules. We report site-selective functi...

Clinical Trials [4297 Associated Clinical Trials listed on BioPortfolio]

Effect of Amino Acids and Sugar Alcohols on Gastric Emptying and Release of Satiation Peptides in Humans

With this study the investigators investigate the effects of amino acids (tryptophan in two different concentrations, leucin) and sugar alcohols (xylitol, erythritol) on satiety mechanisms...

Optimize RV Follow-up Selective Site Pacing Clinical Trial

The purpose of the Optimize RV Follow-Up study is to determine the long-term effect of selective site pacing. Selective site pacing refers to which area of the right ventricle the lead is ...

Tryptophan and Behavior Therapy for Cocaine Abuse - 1

The purpose of this study is to assess the efficacy of tryptophan vs. placebo, and voucher payments vs. a control condition, in the treatment of cocaine dependence.

Optimize RV Selective Site Pacing Clinical Trial

The purpose of the Optimize RV study is to determine the long-term effect of selective site pacing. Selective site pacing refers to which area of the right ventricle the lead is placed. T...

The Role of Serotonin in Hot Flashes After Breast Cancer

The purpose of this proposal is to improve our understanding of the role of tryptophan and serotonin in hot flashes. The main hypothesis is that alterations in tryptophan and serotonin lev...

Medical and Biotech [MESH] Definitions

An oxidation product of tryptophan metabolism. It may be a free radical scavenger and a carcinogen.

A dioxygenase with specificity for the oxidation of the indoleamine ring of TRYPTOPHAN. It is a LIVER-specific enzyme that is the first and rate limiting enzyme in the kynurenine pathway of TRYPTOPHAN catabolism.

Peptides derived from proglucagon which is also the precursor of pancreatic GLUCAGON. Despite expression of proglucagon in multiple tissues, the major production site of glucagon-like peptides (GLPs) is the INTESTINAL L CELLS. GLPs include glucagon-like peptide 1, glucagon-like peptide 2, and the various truncated forms.

The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.

An enzyme that activates tryptophan with its specific transfer RNA. EC 6.1.1.2.

Quick Search


DeepDyve research library

Relevant Topic

Nutrition
Within medicine, nutrition (the study of food and the effect of its components on the body) has many different roles. Appropriate nutrition can help prevent certain diseases, or treat others. In critically ill patients, artificial feeding by tubes need t...


Searches Linking to this Article