1,6‐hexanediol diacrylate‐crosslinked polystyrene: Preparation, characterization, and application in peptide synthesis

Arunan, C.; Pillai, V. N. Rajasekharan

doi:10.1002/app.11538

Cited by 10 publications

(2 citation statements)

References 21 publications

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“…Three% TTEGDA cross-linked polystyrene (TTEGDA-PS), its chloromethylated derivative (TTEGDA-PS-Cl), and chloromethyl methyl ether (CMME) were prepared using the reported procedures. 43,44,45 To a suspension of chloromethylated resin (2 g), 1 g oxazolidone and 1 mL pyridine were added. The mixture was refluxed for 24 h at 110°C.…”

Section: Methodsmentioning

confidence: 99%

Microwave-assisted oxidative coupling of thiols using polystyrene supported bromoderivatives of 2-oxazolidone

Mathew

Koshy³

2021

Polymers and Polymer Composites

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Polymer-supported reagents have become popular in synthetic organic chemistry over the past decades. But the kinetics of polymer-supported reactions is slow compared to solution phase synthesis because of the poor diffusion of the reactants through the macromolecular polymer matrix. This difficulty can be reduced to a great extent by performing polymer-supported reactions under microwave (MW) conditions. The present work is focussed on the design and development of an innovative, powerful, MW stable and recyclable polymeric reagent prepared by attaching bromoderivative of 2-oxazolidone into the macromolecular matrix of polystyrene. 3% cross-linked polystyrene was prepared by free radical aqueous suspension polymerization technique using tetra ethylene glycol diacrylate as the cross-linking agent and the resulting beads were functionalized by chloromethylation followed by reaction with 2-oxazolidone. Bromine functionality is introduced into the polymer by treating with bromine in carbon tetrachloride. The synthetic utility of the prepared polymeric reagent was demonstrated by the oxidative coupling of thiols to disulfides under MW irradiation. No over oxidation was observed in this protocol and the utilization of polystyrene support simplifies work up and product isolation. The synthesised polymeric reagent displayed good cyclic stability up to five cycles without any substantial decrease in bromine content and satisfactory storage stability under normal laboratory condition. Moreover this may be the first report that uses MW energy for the oxidation of thiols to disulfides using polymer-supported reagents. [Formula: see text]

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Section: Methodsmentioning

confidence: 99%

Microwave-assisted oxidative coupling of thiols using polystyrene supported bromoderivatives of 2-oxazolidone

Mathew

Koshy³

2021

Polymers and Polymer Composites

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“…In the refinement of solid‐phase peptide synthesis, much attention has been focused on the development of new polymeric supports with improved polarity to that of the original Merrifield resin, which include polyamide‐based supports, poly(ethylene glycol)–polystyrene (PS) graft resins, poly(ethylene glycol)‐poly(acrylamide) (PEGA, polyoxyethylene‐polyoxypropylene (POEPOP), polyoxyethylene‐polystyrene (POEPS), crosslinked ethoxylate acrylate resin (CLEAR), superpermeable organic combinatorial chemistry resin (SPOCC), hydroxy‐ and amine‐functionalized resin (HYDRA), JandaJel, and crosslinked polystyrene‐ethylene glycol acrylate resin (CLPSER) 6–16. As an alternate route, a series of supports were developed in our laboratories by the replacement of the rigid hydrophobic divinylbenzene crosslinker by flexible hydrophilic crosslinkers 17–19…”

Section: Introductionmentioning

confidence: 99%

A novel chemically and mechanically stable glycerol‐based crosslinked polystyrene support for polypeptide synthesis: A comparative study with Merrifield resin

Sasikumar

Kumar

Pillai

2004

J of Applied Polymer Sci

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ABSTRACT:A novel chemically and mechanically stable polymer support for solid-phase peptide synthesis with excellent swelling performance in various organic solvents is described. The crosslinked polymer in its bead form was prepared by the aqueous suspension polymerization of the styrene and tri(propylene glycol) glycerolate diacrylate. The support is unique because the hydroxyl group is introduced into the polymer support in the polymerization step itself, which makes it highly cost effective. The hydroxyl functionality of the crosslinker in the polymer was used as a growth site for peptide synthesis, thus minimizing the incompatibility arising because of the styrene core as compared to styrene-based polymer supports currently used in polypeptide synthesis. The utility of the resin for solid-phase peptide synthesis was tested by the synthesis of a 19-residue peptide amide of the envelope region of hepatitis C viral polyprotein and was compared with Merrifield resin by the 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluoro phosphate/1-hydroxy benzatriazole method with a Rink amide linker. The molecular character of the polymer and the extent of crosslinking density on the dependence of the reactivity of the attached amino groups were investigated by a reactivity study of the amide bond formation of a model Val-Ala dipeptide. Enhanced swelling, the increased rate of aminoacylation, and the high purity of the peptides synthesized on the novel support highlighted the influence of the polarity of the solid support in the solid-phase synthesis.

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Polystyrene-supported bromoderivative of 2-pyrrolidone: synthesis, characterization and application in microwave-assisted bromination reactions

Mathew

Koshy

2021

Polym. Bull.

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1,6‐hexanediol diacrylate‐crosslinked polystyrene: Preparation, characterization, and application in peptide synthesis

Cited by 10 publications

References 21 publications

Microwave-assisted oxidative coupling of thiols using polystyrene supported bromoderivatives of 2-oxazolidone

Microwave-assisted oxidative coupling of thiols using polystyrene supported bromoderivatives of 2-oxazolidone

A novel chemically and mechanically stable glycerol‐based crosslinked polystyrene support for polypeptide synthesis: A comparative study with Merrifield resin

Polystyrene-supported bromoderivative of 2-pyrrolidone: synthesis, characterization and application in microwave-assisted bromination reactions

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