A Late-Stage Synthetic Approach to Lanthionine-Containing Peptides via S-Alkylation on Cyclic Sulfamidates Promoted by Molecular Sieves
| Autor: | Valentina Verdoliva, Gonzalo Jiménez-Osés, Stefania De Luca, Michele Saviano, Pablo Tovillas, Jesús M. Peregrina, Giuseppe Digilio, Valeria Menchise |
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| Rok vydání: | 2018 |
| Předmět: |
Alanine
Alkylation 010405 organic chemistry Lanthionine-Containing Peptides Organic Chemistry Molecular Conformation Lantibiotics Sulfides 010402 general chemistry Ring (chemistry) Molecular sieve 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Thioether Physical and Theoretical Chemistry Chemoselectivity Sulfonic Acids Peptides Lanthionine |
| Zdroj: | Organic letters 20 (2018): 7478–7482. doi:10.1021/acs.orglett.8b03254 info:cnr-pdr/source/autori:De Luca, Stefania; Digilio, Giuseppe; Verdoliva, Valentina; Saviano, Michele; Menchise, Valeria; Tovillas, Pablo; Jiménez-Osés, Gonzalo; Peregrina, Jesus M./titolo:A Late-Stage Synthetic Approach to Lanthionine-Containing Peptides via S-Alkylation on Cyclic Sulfamidates Promoted by Molecular Sieves/doi:10.1021%2Facs.orglett.8b03254/rivista:Organic letters (Print)/anno:2018/pagina_da:7478/pagina_a:7482/intervallo_pagine:7478–7482/volume:20 |
| ISSN: | 1523-7052 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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