HYDRA: A novel hydroxy and amine functionalised resin synthesised by reductive amination of PEG aldehyde and a polyamine

Abstract

A chemically inert poly(ethylene glycol) (PEG)-based resin was synthesised by reductive amination of a mixture of mono-and dialdehyde PEG 1500 and the branched cross-linker tris(2-aminoethyl)amine. This unique concept of resin polymerisation yields a polar resin with two functionalities present (OH and NH). The resin loading could be tuned between 0.33 and 0.80 mmol OH per gram and 0.88 and 0.24 mmol NH per gram by varying the monomer composition in the polymerisation mixture. The resin was found to exhibit excellent swelling properties in a broad range of solvents, and was stable towards strongly acidic and basic conditions for weeks. Furthermore, both an octaand a decapeptide were successfully assembled independently on the different functionalities. In addition, the resin was shown to be fully permeable to a 27 kDa protease.

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

“…In addition, a high degree of crosslinking usually meant better mechanical stability and flexible ethereal type polymer chains meant more favorable and general swelling characteristics. This work converged to their natural conclusion through the development of resins such as the POEPS (polyoxyethylene-polystyrene), [21] POE-POP (polyoxyethylene-polyoxypropylene), [21] HYDRA (hydroxy-and amine-functionalized resin) [22] and EXPO [23] resins from the mid 1990s onwards, as well as probably reaching its zenith through the SPOCC (superpermeable organic combinatorial chemistry) [24] resin and ChemMatrix (NovaPEG). [25] POEPS is prepared by radical copolymerization of PEG that have been homo-or dialkylated with 4-vinylbenzyl chloride or 4-vinylphenylpropyl chloride, either as bulk or inverse suspension copolymerization.…”

The effect of pendant hydrophobicity on the biological efficacy of polyethylenimine conjugate

“…The hydroxyl group of polyethylene glycol monomethyl ether with a molecular weight of 350 (PEG) was oxidated to be an aldehyde group as described elsewhere [30]. A mixture of 20 mL DMSO and 180 mL DCM was kept stirring for 10 min at room temperature, and then cooled in a dry ice/methanol bath for an additional 10 min.…”

Enhancement of the enzymatic digestibility of sugarcane bagasse by steam pretreatment impregnated with hydrogen peroxide

“…The group of Meldal expanded the family of PEG‐based resins by developing POEPOP,32, 33 POEPS‐3,34 SPOCC35 and HYDRA, because many organic reactions are not compatible with the amide bonds present in the PEGA resin 36…”

“…The HYDRA resin, another polymer developed by the group of Meldal,36 consists of PEG chains linked together by polyamine branching units to form a cross‐linked polymeric system. It is prepared by polymerisation, via reductive amination, between PEG aldehyde and a polyamine.…”

“… Preparation and structure of HYDRA polymer. HYDRA polymer is based on PEG monomers functionalised with mono‐ or dialdehyde and the branched with the cross‐linker tris(2‐aminoethyl)amine 36…”