“High-load” polyethylene glycol-polystyrene (PEG-PS) graft supports for solid-phase synthesis

Abstract

The choice of a polymeric support is a key factor for the success of solid‐phase methods for syntheses of organic compounds and biomolecules such as peptides and oligonucleotides. Classical Merrifield solid‐phase peptide synthesis (SPPS), performed on low cross‐linked hydrophobic polystyrene (PS) beads, sometimes suffers from sequence‐dependent coupling difficulties. The concept of incorporating polyethylene glycol (PEG) into supports for solid‐phase synthesis represents a successful approach to alleviating such problems. Previous reports from our laboratories have shown the advantages of “low‐load” PEG–PS (0.15–0.25 mmol/g) for SPPS. Herein, we demonstrate that the beneficial aspects of the PEG–PS concept can be extended with resins that have higher loadings (0.3–0.5 mmol/g). © 1999 John Wiley & Sons, Inc. Biopoly 47: 365–380, 1998

Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linker

“…Jandajel resin for example features crosslinking of PS chains by tetrahydrofuran derivatives [29–30]. To improve the swelling behavior of PS resins in polar solvents, the PS core was grafted with polyethylene glycol (PEG) chains [31], resulting in solid supports such as Tentagel, Hypogel or Argogel. These resins were successfully used for the synthesis of peptides [31].…”

“…To improve the swelling behavior of PS resins in polar solvents, the PS core was grafted with polyethylene glycol (PEG) chains [31], resulting in solid supports such as Tentagel, Hypogel or Argogel. These resins were successfully used for the synthesis of peptides [31]. Meldal and co-workers developed PEGA resins [32] with good swelling behavior in water and polar solvents.…”

Slightly modifying pseudoproline dipeptides incorporation strategy enables solid phase synthesis of a 54 AA fragment of caveolin‐1 encompassing the intramembrane domain

“…The peptide was synthesized using conventional solid phase Fmoc/ tert ‐butyl ( t Bu) chemistry with a 433A peptide synthesizer on a 100 µmole scale 18. Considering the swelling properties of PEG and PEG‐Polystyrene based resins and their effectiveness for difficult sequences synthesis 19, 20, we decided to choose a low‐loading (0.23 mmole/g) NovaSyn®TGR resin (Merck chemicals Ntd) as solid support. This resin is derivatised with a modified Rink linker, which generates the carboxamide form of the peptide when subjected to TFA cleavage.…”

Preparation of PEGA grafted poly(chloromethylstyrene-co-ethylene glycol dimethacrylate) monolith for high-efficiency solid phase peptide synthesis under continuous flow techniques

“…In Scheme 2, PEGA was used as monomer that contained one PEG chain. Kates et al [31] ever studied that PEG with different molecular weights (in the range of from 600 to 2001) were grafted onto polystyrene resins for increasing the loading capacity of the modified resins, which showed a decreasing trend with molecular weight of PEG due to the steric hindrance. To obtain high loading capacity, the monomer with low molecular weight (Mn ¼ 375), in this study, was selected for grafting copolymerization.…”