Lanthionine Peptides by S-Alkylation with Substituted Cyclic Sulfamidates promoted by Activated Molecular Sieves: Effects of the Sulfamidate Structure on the Yield
Lanthionine Peptides by S-Alkylation with Substituted Cyclic Sulfamidates promoted by Activated Molecular Sieves: Effects of the Sulfamidate Structure on the Yield(336 views) De Luca S, Digilio G, Verdoliva V, Tovillas P, Jimenez-oses G, Peregrina JM
J Org Chem (ISSN: 0022-3263linking), 2019 Nov 15; 84(22): 14957-14964.
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.
Departamento de Quimica, Centro de Investigacion en Sintesis Quimica , Universidad de La Rioja , 26006 Logrono , Spain.
CIC bioGUNE , Bizkaia Technology Park, Building 800 , 48170 Derio , Spain.
References: Not available.
Lanthionine Peptides by S-Alkylation with Substituted Cyclic Sulfamidates promoted by Activated Molecular Sieves: Effects of the Sulfamidate Structure on the Yield
A green and efficient method for preparing lanthionine peptides by a highly chemoselective and stereochemically controlled procedure is presented. It involves an S-alkylation reaction, promoted by activated molecular sieves, on chiral cyclic sulfamidates, both N-protected and unprotected. Of note, the reaction yield was high also for cyclic sulfamidates bearing a free amine group, while other strategies failed to achieve a ring-opening nucleophilic reaction with N-unprotected substrates. To prove the feasibility of the procedure, the synthesis of a thioether ring B mimetic of the natural lantibiotic haloduracin beta was performed.
Lanthionine Peptides by S-Alkylation with Substituted Cyclic Sulfamidates promoted by Activated Molecular Sieves: Effects of the Sulfamidate Structure on the Yield
Lanthionine Peptides by S-Alkylation with Substituted Cyclic Sulfamidates promoted by Activated Molecular Sieves: Effects of the Sulfamidate Structure on the Yield