A Late-Stage Synthetic Approach to Lanthionine-Containing Peptides via S-Alkylation on Cyclic Sulfamidates Promoted by Molecular Sieves

Stefania De Luca, Giuseppe Digilio, Valentina Verdoliva, Michele Saviano, Valeria Menchise, Pablo Tovillas, Gonzalo Jiménez-Osés, Jesus M. Peregrina

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

A one-pot, high-yield procedure for synthesizing lanthionine-containing peptides was developed. It relies on the S-alkylation of cysteine-containing peptides with chiral cyclic sulfamidates. The key feature of this approach is the use of mild reaction conditions (only activated molecular sieves are employed as the catalyst), leading to good chemoselectivity and excellent stereochemical control. The potential of the new methodology has been investigated by synthesizing the thioether ring of a natural lantibiotic, Haloduracin β.

Lingua originaleInglese
pagine (da-a)7478-7482
Numero di pagine5
RivistaOrganic Letters
Volume20
Numero di pubblicazione23
DOI
Stato di pubblicazionePubblicato - 7 dic 2018

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