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A New Photochemical Method For The Preparation Of Amino Acid-α-Phenylthioesters And Peptide-α-Phenylthioesters, Tyrone Hogenauer
A New Photochemical Method For The Preparation Of Amino Acid-α-Phenylthioesters And Peptide-α-Phenylthioesters, Tyrone Hogenauer
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We describe the development of a novel resin with a photoreactive N-acylnitroindoline linker that allows for the synthesis of amino acid- (in solution) or peptide-α-thioesters using standard Fmoc/t-Bu standard solid phase peptide synthesis (SPPS). Recent advances have shown that the yields of this thioesterification reaction have dramatically increased due to a simple change in the order of addition of reagents. Upon illumination with UV-light, in the presence of N-hydroxybenzotriazole (HOBt), the amino acid- or peptide-α-OBt ester is generated by direct photo-release from the nitroindoline linker with minimal epimerization, followed by reaction with thiophenol in the dark to produce amino acid-α-phenylthioesters …