Protein Thioacylation. 1. Reagents Design and Synthesis

Lévesque, Guy; Arsène, Philippe; Fanneau-Bellenger,; Tn, Pham

doi:10.1021/bm000288k

Cited by 23 publications

(12 citation statements)

References 80 publications

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“…for conjugation with a polymer) versus activated carboxylic acids makes this route more challenging. 2 Alternatively, lysine residues may react by amidination with imidoesters (4) at elevated pH (B9) or with imidothiolane (Traut's reagent, 5) near pH 8, 13 the latter being useful for introducing thiol groups. Generally, the latter reaction is selective towards surface accessible lysine residues, though the generated thiol groups may conceivably form intra-or intermolecular disulfide bonds with cysteine residues.…”

Section: Introductory Remarksmentioning

confidence: 99%

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Peptide/protein–polymer conjugates: synthetic strategies and design concepts

2008

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This feature article provides a compilation of tools available for preparing well-defined peptide/protein-polymer conjugates, which are defined as hybrid constructs combining (i) a defined number of peptide/protein segments with uniform chain lengths and defined monomer sequences (primary structure) with (ii) a defined number of synthetic polymer chains. The first section describes methods for post-translational, or direct, introduction of chemoselective handles onto natural or synthetic peptides/proteins. Addressed topics include the residue- and/or site-specific modification of peptides/proteins at Arg, Asp, Cys, Gln, Glu, Gly, His, Lys, Met, Phe, Ser, Thr, Trp, Tyr and Val residues and methods for producing peptides/proteins containing non-canonical amino acids by peptide synthesis and protein engineering. In the second section, methods for introducing chemoselective groups onto the side-chain or chain-end of synthetic polymers produced by radical, anionic, cationic, metathesis and ring-opening polymerization are described. The final section discusses convergent and divergent strategies for covalently assembling polymers and peptides/proteins. An overview of the use of chemoselective reactions such as Heck, Sonogashira and Suzuki coupling, Diels-Alder cycloaddition, Click chemistry, Staudinger ligation, Michael's addition, reductive alkylation and oxime/hydrazone chemistry for the convergent synthesis of peptide/protein-polymer conjugates is given. Divergent approaches for preparing peptide/protein-polymer conjugates which are discussed include peptide synthesis from synthetic polymer supports, polymerization from peptide/protein macroinitiators or chain transfer agents and the polymerization of peptide side-chain monomers.

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Section: Introductory Remarksmentioning

confidence: 99%

“…13 5 Useful for generation of a thiol group. 13 6 Exchange reactions with free thiol groups can be overcome by adding excess R'SH. 14…”

Section: Introductory Remarksmentioning

confidence: 99%

Peptide/protein–polymer conjugates: synthetic strategies and design concepts

2008

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“…The RAFT technique owes its success to a family of organic molecules containing the thio‐carbonyl‐thio group, known as RAFT agents 40–42. There are however shortcomings, i.e., the thio‐carbonyl‐thio group can be hydrolyzed by basic species such as hydroxide ions, and primary and secondary amines 37, 43–46. Thus, the synthesis of positively charged RAFT agents is a great challenge because of the inherent instability of the thio‐carbonyl‐thio group in a basic environment, since most of the positively charged organic species originate from amines.…”

Section: Introductionmentioning

confidence: 99%

Novel Cationic RAFT‐Mediated Polystyrene/Clay Nanocomposites: Synthesis, Characterization, and Thermal Stability

Samakande

Juodaityte

Sanderson

et al. 2008

Macro Materials & Eng

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Two novel cationic RAFT agents, PCDBAB and DCTBAB, were anchored onto MMT clay to yield RAFT‐MMT clays. The RAFT‐MMT clays were then dispersed in styrene where thermal self‐initiation polymerization of styrene to give rise to exfoliated PS/clay nanocomposites occurred. The RAFT agents anchored onto the clay layers successfully controlled the polymerization process resulting in controlled molecular masses and narrow polydispersity indices. The nanocomposites prepared showed enhanced thermal stability, which was a function of the clay loading, clay morphology, and slightly on molecular mass.magnified image

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“…The P1 is then employed to initiate the polymerization of allyl methacrylate to afford a triblock copolymer P2, where the concentration of RAFT end groups and radical initiator is kept constant throughout the polymerization. As the thiocarbonylthio end group of copolymers is considered to be unstable and biotoxic, the thiocarbonylthio group in P2 has been removed via mild one‐pot aminolysis and Michael addition process to obtain P3. And then the l ‐cysteine hydrochloride is conjugated with the pendant vinyl groups through thiol–ene addition to obtain the copolymer P4.…”

Section: Resultsmentioning

confidence: 99%

Novel Anti‐Biofouling Soft Contact Lens: l‐Cysteine Conjugated Amphiphilic Conetworks via RAFT and Thiol–Ene Click Chemistry

Zhang

Liu

Wang

et al. 2017

Macromolecular Bioscience

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A unique l-cysteine conjugated antifouling amphiphilic conetwork (APCN) is synthesized through end-crosslinking of well-defined triblock copolymers poly(allyl methacrylate)-b-poly(ethylene glycol)-b-poly(allyl methacrylate) via a combination of reversible addition-fragmentation chain transfer (RAFT) polymerization and thiol-ene "click" chemistry. The synthesized poly(ethylene glycol) macro-RAFT agent initiates the polymerization of allyl methacrylate in a controlled manner. The vinyl pendant groups of the precursor partially conjugate with l-cysteine and the rest fully crosslink with mercaptopropyl-containing siloxane via thiol-ene click chemistry under UV irradiation into APCNs, which show distinguished properties, that is, excellent biocompatibility, more than 39.6% water content, 101 barrers oxygen permeability, optimized mechanical properties, and more than 93% visible light transmittance. What's more, the resultant APCNs exhibit eminent resistance to protein adsorption, where the bovine serum albumin and lysozyme adsorption are decreased to 12 and 21 µg cm , respectively. The outstanding properties of APCNs depend on the RAFT controlled method, which precisely designs the hydrophilic/hydrophobic segments and eventually greatly improves the crosslinking efficiency and homogeneity. Meantime, the l-cysteine monolayer can effectively reduce the surface hydrophobicity and prevent protein adsorption, which exhibits the viability for antifouling surface over and under ophthalmic devices, suggesting a promising soft contact lens.

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Protein Thioacylation. 1. Reagents Design and Synthesis

Cited by 23 publications

References 80 publications

Peptide/protein–polymer conjugates: synthetic strategies and design concepts

Peptide/protein–polymer conjugates: synthetic strategies and design concepts

Novel Cationic RAFT‐Mediated Polystyrene/Clay Nanocomposites: Synthesis, Characterization, and Thermal Stability

Novel Anti‐Biofouling Soft Contact Lens: l‐Cysteine Conjugated Amphiphilic Conetworks via RAFT and Thiol–Ene Click Chemistry

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