Novel non-PEG derived polyethers as solid supports. 2. Solid-phase synthesis studies.
Novel non-PEG derived polyether resins, coined SLURPS (Superior Liquid Uptake Resins for Polymer-supported Synthesis), were studied for their performance in solid-phase synthesis. Novel amino functional resins, SLURPS-NH2, 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 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 OsO4 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 at much higher loading levels than standard amphiphilic resins of similar solvent compatibility.
Cavalli
Gabriel
G
Department of Chemistry, Imperial College London, South Kensington Campus, London, SW7 2AZ, UK.
Shooter
Andrew G
AG
Pears
David A
DA
Wellings
Donald A
DA
Gulzar
Saeed
S
Steinke
Joachim H G
JH
D000475:Alkenes / Q000737:chemistry; D004743:Enkephalin, Leucine / Q000138:chemical synthesis*; D004987:Ethers / Q000737:chemistry*; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D018377:Neurotransmitter Agents / Q000138:chemical synthesis*; D009993:Osmium Tetroxide / Q000737:chemistry; D010091:Oximes / Q000737:chemistry; D011092:Polyethylene Glycols / Q000737:chemistry*; D019904:Polymethyl Methacrylate / Q000737:chemistry; D012117:Resins, Synthetic / Q000138:chemical synthesis*; D012997:Solvents / Q000737:chemistry
D000475:Alkenes; D004987:Ethers; D018377:Neurotransmitter Agents; D010091:Oximes; D012117:Resins, Synthetic; D012997:Solvents; D011092:Polyethylene Glycols; D004743:Enkephalin, Leucine; D019904:Polymethyl Methacrylate; D009993:Osmium Tetroxide