A Late-Stage Synthetic Approach to Lanthionine-Containing Peptides via S-Alkylation on Cyclic Sulfamidates Promoted by Molecular Sieves(369 views) De Luca S, Digilio G, Verdoliva V, Saviano M, Menchise V, Tovillas P, Jimenez-oses G, Peregrina JM
Org Lett (ISSN: 1523-7052electronic, 1523-7052linking, 1523-7060), 2018 Nov 14; 20(23): 7478-7482.
Institute of Biostructures and Bioimaging , National Research Council , 80134 Naples , Italy., Department of Science and Technologic Innovation , Universita del Piemonte Orientale "A. Avogadro" , 15121 Alessandria , Italy., Institute of Crystallography , National Research Council , 70126 Bari , Italy., Institute of Biostructures and Bioimaging , National Research Council , c/o Molecular Biotechnology Center, 10126 Turin , Italy., Departamento de Quimica, Centro de Investigacion en Sintesis Quimica , Universidad de La Rioja , 26006 Logrono , Spain.,
References: Not available.
A Late-Stage Synthetic Approach to Lanthionine-Containing Peptides via S-Alkylation on Cyclic Sulfamidates Promoted by Molecular Sieves
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 beta.
A Late-Stage Synthetic Approach to Lanthionine-Containing Peptides via S-Alkylation on Cyclic Sulfamidates Promoted by Molecular Sieves