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Isoacyl Dipeptides
Isoacyl Dipeptides are used to increase the coupling efficiencies during Fmoc-SPPS. The acetylation of the hydroxyl group of a Boc-protected serine or threonine with an Fmoc-amino acid leads to the formation of depsipeptides in which the peptide chain contains an ester bond instead of an amide bond at the respective position. In analogy to pseudoprolines, this leads to a conformational disruption preventing aggregation. Even after cleavage from the Fmoc-SPPS resin, the depsipeptide benefits of increased solubility compared to the native peptide sequence, thus facilitating further purification.
