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Title

Solid-Phase Synthesis of Head to Side-Chain Tyr-Cyclodepsipeptides Through a Cyclative Cleavage From Fmoc-MeDbz/MeNbz-resins

AuthorsAcosta, Gerardo A.; Murray, Laura; Royo, Miriam ; De la Torre, B. G.; Alberício, Fernando
KeywordsCyclothiodepsipeptides
Heterodetic cyclic peptides
Homodetic cyclic peptides
Native chemical ligation
Solid-phase peptide synthesis
Issue Date22-Apr-2020
PublisherFrontiers Media
CitationFrontiers in Chemistry 8: 298 (2020)
AbstractCyclic depsipeptides constitute a fascinating class of natural products. Most of them are characterized by an ester formed between the β-hydroxy function of Ser/Thr -and related amino acids- and the carboxylic group of the C-terminal amino acid. Less frequent are those where the thiol of Cys is involved rendering a thioester (cyclo thiodepsipeptides) and even less common are the cyclo depsipeptides with a phenyl ester coming from the side-chain of Tyr. Herein, the preparation of the later through a cyclative cleavage using the Fmoc-MeDbz/MeNbz-resin is described. This resin has previously reported for the synthesis of cyclo thiodepsipeptides and homodetic peptides. The use of that resin for the preparation of all these peptides is also summarized. © Copyright © 2020 Acosta, Murray, Royo, de la Torre and Albericio.
Publisher version (URL)https://doi.org/10.3389/fchem.2020.00298
URIhttp://hdl.handle.net/10261/213949
DOI10.3389/fchem.2020.00298
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