Novel Non-PEG Derived Polyethers as Solid Supports. 2. Solid-Phase Synthesis Studies

Abstract

Novel non-PEG derived polyether resins, coined SLURPS (Superior Liquid Uptake Resins forPolymer-supported Synthesis), were studied for their performance in solid-phase synthesis. Novel amino functional resins, SLURPS-NH 2 , were prepared with a loading of up to 8.5 mmol/g and employed successfully in the solid-phase synthesis of Leu-Enkephalin. The peptide was obtained with the same 2 purity when compared to its synthesis with commercial standard poly(dimethyl acrylamide) resins.Furthermore we show loading and cleavage of aromatic carboxylic acids in excellent yield. The advantageous solvent compatibility of our support was demonstrated through the biphasic dihydroxylation of alkenes with OsO 4 in t-BuOH/water mixtures producing bound 1,2-diols and synthesis and removal of a bound oxime using ethanol/water mixtures both in excellent yields. Reactions were easily monitored by gel-phase NMR and FTIR These results show that SLURPS are very well suited for organic transformations using highly polar solvent mixtures and reagents and this at much higher loading levels than standard amphiphilic resins of similar solvent compatibility. Graphical Abstract:O OH SLURPS

Porous polymer particles—A comprehensive guide to synthesis, characterization, functionalization and applications

“…Lack of coloring of the resin judged by the naked eye designates the completeness of the main reaction. In the classical fluorenylmethyloxycarbonyl (Fmoc) based solid phase peptide synthesis (Scheme 1), a resin possessing -NH 2 or -OH groups is treated with an Fmoc protected amino acid in the presence of some well known organic catalysts [321]. Here the completeness of the reaction is checked with a color test, i.e.…”

Organic Polymer Supports for Synthesis and for Reagent and Catalyst Immobilization

“…Mixtures of 141 , 142 , and cross-linker 143 ( 2 mol %) were cationically polymerized with BF 3 −Et 2 O to afford the polymer 144 that swelled exceptionally well in a variety of polar solvents and contained loading levels of up to 8.5 mmol g −1 (Scheme ). Conversion of the acetate groups to bromides ( 145 ) allowed for installation of various linker groups so that solid-phase peptide synthesis could be performed . It should be noted that the great swelling of this resin allowed for reactions to be easily monitored by gel-phase NMR and FTIR spectroscopy.…”

“…Conversion of the acetate groups to bromides (145) allowed for installation of various linker groups so that solid-phase peptide synthesis could be performed. 190 It should be noted that the great swelling of this resin allowed for reactions to be easily monitored by gel-phase NMR and FTIR spectroscopy.…”