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
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.