A5044397326- Chemical Synthesis and Analysis
- Click Chemistry and Applications
- Peptidase Inhibition and Analysis
- Biochemical and Structural Characterization
- Sulfur-Based Synthesis Techniques
- Carbohydrate Chemistry and Synthesis
- Protein Hydrolysis and Bioactive Peptides
- Advanced biosensing and bioanalysis techniques
- Chemical Synthesis and Reactions
- RNA Interference and Gene Delivery
- Advanced Biosensing Techniques and Applications
- DNA and Nucleic Acid Chemistry
- Gene expression and cancer classification
- Synthetic Organic Chemistry Methods
- Redox biology and oxidative stress
- Ubiquitin and proteasome pathways
- Monoclonal and Polyclonal Antibodies Research
- Stroke Rehabilitation and Recovery
- Protein Structure and Dynamics
- Glycosylation and Glycoproteins Research
- Titanium Alloys Microstructure and Properties
- Protein Tyrosine Phosphatases
- Antimicrobial Peptides and Activities
- Synthesis and Reactivity of Sulfur-Containing Compounds
- PI3K/AKT/mTOR signaling in cancer
Université de Lille
2015-2025
Institut Pasteur de Lille
2014-2024
Center for Infection and Immunity of Lille
2019-2024
Centre Hospitalier Universitaire de Lille
2020-2024
Centre National de la Recherche Scientifique
2012-2024
Inserm
2019-2024
Royal Society of Chemistry
2015
Harvard University Press
2015
Stanford University
2015
Massachusetts Institute of Technology
2015
The reaction of a peptide featuring bis(2-sulfanylethyl)amino (SEA) group on its C-terminus with cysteinyl in water at pH 7 and 37 °C leads to the chemoselective regioselective formation native bond. This method called SEA ligation enriches repertoire available chemist. Preparation an innovative solid support which allows straightforward synthesis fragments using standard Fmoc/tert-butyl phase procedures is also described.
Three in one: Native chemical ligation (NCL) and bis(2-sulfanylethyl)amido (SEA) allow the one-pot assembly of three peptide segments N-to-C direction. The SEA group (see picture, blue) is switched off by intramolecular disulfide bond formation during NCL. Then, a phosphine switches it on to trigger second step. K1 domain hepatocyte growth factor was synthesized found be biologically active.
We describe the Fmoc solid-phase synthesis of peptide thioesters based on alkylation safety-catch sulfonamide linker with a protected 2-mercaptoethanol derivative. The thioester is generated solid phase after chain assembly as consequence an intramolecular N,S-acyl shift. Depending stability spacer separating from resin toward TFA, treatment peptidyl TFA led to soluble or supported deprotected thioester.
The design of novel methods giving access to peptide alkylthioesters, the key building blocks for protein synthesis using Native Chemical Ligation, is an important area research. Bis(2-sulfanylethyl)amido peptides (SEA peptides) 1 equilibrate in aqueous solution with S-2-(2-mercaptoethylamino)ethyl thioester 2 through N,S-acyl shift mechanism. HPLC was used study rate equilibration different C-terminal amino acids and position equilibrium as a function pH. We show also that form can...
SeEA latent selenoester: go fast by switching to selenium.
Thiazolidine thioester peptides were synthesized by reacting bis(2-sulfanylethyl)amido with glyoxylic acid at pH 1. A significant increase in Native Chemical Ligation (NCL) rate was observed thiazolidine thioesters compared to 3-mercaptopropionic acid-thioester analogues. The method is of particular interest for accelerating valine-cysteine peptide bond formation.
Abstract Cyclic peptide-based therapeutics have a promising growth forecast that justifies the development of microfluidic systems dedicated to their production, in phase with actual transitioning toward continuous flow and technologies for pharmaceutical production. The application most popular method peptide cyclization water, i.e., native chemical ligation, under conditions is still unexplored. Herein, we report general strategy fast efficient using ligation homogeneous conditions. relies...
The use of the N-acetoacetyl protecting group for N-terminal cysteine residue enabled creation an efficient and mild one-pot native chemical ligation/SEA ligation sequence giving access to large cyclic peptides.
The control of cysteine reactivity is paramount importance for the synthesis proteins using native chemical ligation (NCL) reaction. We report that this goal can be achieved in a traceless manner during by appending simple N-selenoethyl group to cysteine. While synthetic organic chemistry cleavage carbon-nitrogen bonds notoriously difficult, we describe (SetCys) loses its selenoethyl arm water under mild conditions upon reduction selenosulfide bond. Detailed mechanistic investigations show...
<title>Abstract</title> <bold>Purpose</bold> Chronic lower back pain is a multifactorial health problem that can involve the intervertebral discs. The objective of present clinical trial was to describe effect trunk exoskeleton on level experienced during standardized activity track. <bold>Materials and Methods</bold> Thirty-one patients with chronic agreed wear device daily perform track as part hospital-based multidisciplinary rehabilitation programme. participants were randomized use day...
Bis(2-sulfanylethyl)amino PEG resin gives access to large peptide thioester segments and functional SUMO-1 conjugates.
Chemical protein synthesis gives access to well-defined native or modified proteins that are useful for studying structure and function. The majority of synthesized up now have been produced using chemical ligation (NCL) in solution. Although there significant advantages assembling large peptides by solid phase ligation, reports such approaches rare. We report a novel method which relies on the chemistry acetoacetyl group ketoxime attachment peptide support, tandem...
Selenopeptides can be transamidated by cysteinyl peptides in water using mild conditions (pH 5.5, 37 °C) the presence of an arylthiol catalyst. Similar also catalyze metathesis selenopeptides. The usefulness selenophosphine derived from TCEP (TCEP═Se) for inhibiting TCEP-induced deselenization selenocysteine residue is reported.
Clustering of synthetic biotinylated K1 domain from HGF/SF by streptavidin is sufficient to generate a potent MET agonist.
Drei in einem: Native chemische Ligation (NCL) und Bis(2-sulfanylethyl)amido(SEA)-Ligation ermöglichen die Kupplung von drei Peptidsegmenten einem Gefäß N-nach-C-Richtung. Die SEA-Gruppe (siehe Bild, blau) liegt während der NCL als intramolekulares Disulfid vor. Für den zweiten SEA-Ligationsschritt wird sie situ mit Phosphin angeschaltet. K1-Domäne des Hepatozyten-Wachstumsfaktors wurde so synthetisiert erwies sich biologisch aktiv. Detailed facts of importance to specialist readers are...
Protein total chemical synthesis enables the atom-by-atom control of protein structure and therefore has a great potential for studying function. Native ligation C-terminal peptide thioesters with N-terminal cysteinyl peptides related methodologies are central to field synthesis. Consequently, methods enabling facile using Fmoc-SPPS value. Herein, we provide detailed protocol preparation bis(2-sulfanylethyl)amino polystyrene resin as starting point bis(2-sulfanylethyl)amido derived from...
Targeting DNA double-strand breaks is a powerful strategy for gene inactivation applications. Without the use of repair plasmid, targeted mutagenesis can be achieved through Non-Homologous End joining (NHEJ) pathways. However, many produced by engineered nucleases may subject to precise re-ligation without loss genetic information and thus are likely unproductive. In this study, we combined endonucleases DNA-end processing enzymes increase efficiency mutagenesis, providing robust efficient...
Abstract The modification of protein electrostatics by phosphorylation is a mechanism used cells to promote the association proteins with other biomolecules. In this work, we show that introducing negatively charged phosphoserines in reactant powerful means for directing and accelerating chemical equipped oppositely arginines. While extra amino acid residues induce no detectable affinity between reactants, they bring site-selectivity reaction otherwise devoid such property. They also enable...
We describe in this paper the preparation and characterization of semicarbazide glass slides their use for fabrication microarrays using site-specific α-oxo semicarbazone ligation. The functional density homogeneity were optimized by analyzing reactivity layer toward a synthetic glyoxylyl fluorescent probe. Oligonucleotide prepared immobilization oligodeoxynucleotides. directly used hybridization assays fluorescence detection displayed significant gain sensibility as compared to aldehyde...
The last two decades have witnessed the rise in power of chemical protein synthesis to point where it now constitutes an established corpus synthetic methods efficiently complementing biological approaches. One factor explaining this spectacular evolution is emergence a new class chemoselective reactions enabling formation native peptide bonds between unprotected peptidic segments, also known as ligation reactions. In recent years, their application has fueled production homogeneous batches...