Convenient method for preparing polystyrene having β-hydroxy group: Its application to the synthesis of polyethylene glycol-grafted polystyrene resin

Park, Byeong-Deog; Lee, Hyeong-Ik; Ryoo, Sun-Jong; Lee, Jun Young

doi:10.1016/s0040-4039(96)02399-4

Cited by 36 publications

(16 citation statements)

References 15 publications

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“…[13] In the same period, a quite elegant way of introducing a nonbenzylic alcohol directly onto non-derivatized and crosslinked PS using propylene oxide and Lewis acid was reported. [14] The alcohol was then grafted with ethylene oxide by anionic polymerization to give a useful resin. [14] An interesting notion to keep in mind is the fact that, of the PEG-grafted crosslinked PS resins, the types that have received the most significant commercial success are prepared by grafting the PEG-chains through polymerization (e.g.…”

Section: Polymer Resins For Polymeric Immobilization the Polystyrene-mentioning

confidence: 99%

“…[14] The alcohol was then grafted with ethylene oxide by anionic polymerization to give a useful resin. [14] An interesting notion to keep in mind is the fact that, of the PEG-grafted crosslinked PS resins, the types that have received the most significant commercial success are prepared by grafting the PEG-chains through polymerization (e.g. TentaGel, ArgoGel) and not installment of prefabricated PEG.…”

Section: Polymer Resins For Polymeric Immobilization the Polystyrene-mentioning

confidence: 99%

“…[6d-6h,29] A very expedient immobilization of proline was reported where succinate modified MeOPEG (14) was directly linked to unprotected trans-4-hydroxy--proline in a rather brute fashion, using diisopropylcarbodiimide (DIC) under neat conditions for 20 h at 140°C (Scheme 2).…”

Section: Proline Immobilization On Linear Polymersmentioning

confidence: 99%

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Polymer‐Supported Chiral Organocatalysts: Synthetic Strategies for the Road Towards Affordable Polymeric Immobilization

2010

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In this microreview, we highlight the field of polymer‐supported organocatalysis, especially immobilized enamine and iminium organocatalysts. We try to formalize the overall synthetic strategies for polymeric immobilization as spanning the area of two overlapping regions, from a copolymer strategy favoured by low‐valued and small catalysts to a classical post‐modification strategy favoured by valuable and/or large catalysts. Organocatalysis is particularly interesting as it is probably best described as being located in the transitional region, and we will trace the historic and factual origins for the unfortunate predispositions towards post‐modification schemes. In addition, we try to identify affordable and useful syntheses of key organocatalyst immobilization intermediates, as well as polymer supports that are more compatible with a broader range of reaction solvent polarity, something of crucial importance in organocatalysis.

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Section: Polymer Resins For Polymeric Immobilization the Polystyrene-mentioning

confidence: 99%

Section: Polymer Resins For Polymeric Immobilization the Polystyrene-mentioning

confidence: 99%

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Polymer‐Supported Chiral Organocatalysts: Synthetic Strategies for the Road Towards Affordable Polymeric Immobilization

2010

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“…Linear tracers were synthesized by polymer analogous hydroxyalkylation of polystyrenes with low polydispersities (Pressure Chemicals, Pittsburgh, PA, USA) and subsequent labeling with the fluorescent dye 6‐(7‐nitrobenzfurazan‐4‐ylamino) hexanoic acid by a Steglich esterification 4, 5. The degree of functionalization was kept low, in the range of 0.1 to 0.3 mol‐%, as verified by UV/vis‐spectroscopy.…”

Section: Experimental Partmentioning

confidence: 99%

Dynamics of Labeled Linear Polystyrenes in Semi‐Dilute Polystyrene Matrices in the Uncross‐Linked and Cross‐Linked States

Susoff

2010

Macromolecular Symposia

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Summary: Linear polystyrene chains that were labeled with a fluorescent dye were enclosed in a semidilute matrix of polystyrene in toluene. The matrix polymers used were suitably functionalized such that they could be photocross-linked in a stepwise and controlled manner without attachment of the tracer chains. The diffusion coefficient of the tracer chains was determined by fluorescence recovery after photobleaching while the state of the matrix was changing from a semidilute solution to a covalently cross-linked gel. The progress of the photocross-linking reaction was macroscopically monitored by rheology. The tracer chains were polystyrenes with molecular weights ranging from 50 000 to 2 000 000 g mol À1 and low polydispersity.They were labeled via polymer analogous reactions with the fluorescent dye 6-(7-nitrobenzfurazan-4-ylamino) hexanoic acid. The matrix polymers covered a similar molecular weight range. The results of these measurements show that the dependence of the diffusion coefficient on the tracer molecular weight in the gel can be described by a scaling law in the sense of the reptation theory whereas distinct deviations of this scaling behavior appear in the sol state. The ratio of the matrix molecular weight and tracer molecular weight in the initial sol state significantly influences the change of the probe dynamics during the sol-gel transition.

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“…The developments of poly(ethylene glycol) (PEG)-grafted PS resin [7][8][9][10] or PS crosslinked with PEG moiety [11][12][13][14][15][16] are some of the approaches to circumvent the problems associated with DVB-based resins. Recently, we have shown the utility of 1,4-butanediol dimethacrylate-crosslinked PS (BDDMA-PS) in solid-phase peptide synthesis (SPPS).…”

Section: Introductionmentioning

confidence: 99%

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

Arunan

Pillai

2002

J of Applied Polymer Sci

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A copolymer of 1,6-hexanediol diacrylate (HDODA) and styrene was prepared by a suspension polymerization method. The resin was characterized by infrared and carbon-13 cross-polarization magic-angle spin ( 13 C CP-MAS) spectroscopy. The topology of the resin was examined by scanning electron microscopy (SEM). The polymer swells extensively in common solvents used for peptide synthesis. The resin exhibited chemical stability even in neat trifluoroacetic acid. The applicability of the new resin was demonstrated by synthesis of Val-Ala-Val-Ala-Ala-Gly, Gln-ValGly-Gln-Val-Glu-Leu-Gly, and Val-Gln-Ala-Ala-Ile-AspTyr-Ile-Asn-Gly. Comparative synthetic studies showed that the new resin is superior to divinylbenzene (DVB)-based resin in the case of the synthesis of hydrophobic peptide sequences.

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Convenient method for preparing polystyrene having β-hydroxy group: Its application to the synthesis of polyethylene glycol-grafted polystyrene resin

Cited by 36 publications

References 15 publications

Polymer‐Supported Chiral Organocatalysts: Synthetic Strategies for the Road Towards Affordable Polymeric Immobilization

Polymer‐Supported Chiral Organocatalysts: Synthetic Strategies for the Road Towards Affordable Polymeric Immobilization

Dynamics of Labeled Linear Polystyrenes in Semi‐Dilute Polystyrene Matrices in the Uncross‐Linked and Cross‐Linked States

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

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