Synthesis, Characterization, and Application of Butanediol Dimethacrylate Cross-Linked Polystyrene: A Flexible Support for Gel Phase Peptide Synthesis

Abstract

We have developed a new cross-linked polymeric support by the copolymerization of styrene and butanediol dimethacrylate (BDODMA) for the solid-phase synthesis of peptides. The resin support was synthesized in various cross-linking densities by radical aqueous suspension polymerization. The copolymer was characterized by IR and 13C NMR techniques. The shape, size, and morphological features of the cross-linked polymer bead were analyzed by scanning electron microscopy. PS-BDODMA polymer support showed excellent swelling properties in all types of solvents that are used in solid-phase peptide synthesis (SPPS). The stability of polymer in various reagents and solvents was tested by IR. The polymer does not show any change in its IR spectrum even after 48 h treatment with TFA, 20% piperidine in DMF, aqueous NaOH, hydroxylamine in aqueous MeOH, and liquor ammonia. The resin can be functionalized with chloromethyl, aminomethyl, and hydroxymethyl groups under various reaction conditions. The efficiency of this new support was demonstrated by the synthesis of few model peptides with very high purity and yield. These peptides were characterized by MALDI TOF MS and amino acid analysis.

Immobilization of catalase on a novel polymer support, crosslinked polystyrene ethylene glycol acrylate resin: Role of the macromolecular matrix on enzyme activity

“…Divinylbenzene-crosslinked polystyrene (PS-DVB), ethylene glycol dimethacrylate crosslinked polystyrene (PS-EGDMA), 24 1,4-butanediol dimethacrylate crosslinked polystyrene (PS-BD-DMA), 25 and the newly synthesized crosslinked polystyrene ethylene glycol acrylate resin (CLPSER) 26 system (2-20 mol %) were used for this investigation. The crosslinked PS resins were functionalized by chloromethylation, followed by amination and incorporation of the enzyme catalase to the support through carboxyl groups with tetramethyluronium hexafluorophosphate (HBTU) coupling, and proteins were estimated by Bradford's method.…”

Structure and properties of microwave transparent crosslinked polystyrene prepared through 3D printing bulk polymerization

“…The kinetics of PS crosslinking through styrene (St)/DVB copolymerization and the mechanism of network formation have been thoroughly studied since 1934 . With these fundamental studies, preparation of crosslinked PS microsphere has merged with great momentum for varieties of applications . Amou et al .…”

Functional segmented polymer networks based on polytetrahydrofuran and poly(vinylbenzyl chloride)

“…Therefore, the development of new materials, which are designed for specific reaction conditions, are of great interest. Examples of making a polymer support more compatible with more polar solvents and reagents are polymer systems that incorporate poly(ethylene glycol) [6], polyester [7] and butanediol dimethacrylate [8]. Janda et al recently described a series of polystyrene polymers that incorporate short flexible polytetrahydrofuran-based cross-linkers, to overcome certain shortcomings of PSt-DVB [9][10].…”