Diastereopure Synthesis of Novel Cyclohexane-Ring-Based Constrained Lanthionine and α-Methyllanthionine through an SN2 Reaction with a β-Bromoalanine as a Key Step
| Autor: | Ángel Carretero, Jaime Gracia-Vitoria, Carlos Cativiela, Iñaki Osante |
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| Přispěvatelé: | Ministerio de Economía y Competitividad (España), Gobierno de Aragón, European Commission |
| Rok vydání: | 2020 |
| Předmět: |
010405 organic chemistry
Organic Chemistry Enantioselective synthesis Lantibiotics 010402 general chemistry Ring (chemistry) 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound Enantiopure drug chemistry Thioether SN2 reaction Derivative (chemistry) Lanthionine |
| Zdroj: | Digital.CSIC. Repositorio Institucional del CSIC instname |
| ISSN: | 1437-2096 0936-5214 |
| DOI: | 10.1055/s-0039-1690790 |
| Popis: | Here we report the diastereopure synthesis of a novel protected lanthionine derivative substituted with a cyclohexane ring as well as the diastereopure synthesis of an α-methyllanthionine derivative. By starting from enantiopure α,β-cyclohexane-substituted cystine, or α-methylcysteine, we designed a straightforward route that permits the preparation of orthogonally protected modified lanthionines in diastereopure form. The key step of the methodology is the formation of a thioether bond through the use of an β-bromoalanine derivative. The strategy developed should be valuable in the preparation of a wide range of modified constrained lanthionines that might be finally attached to a peptide sequence, which would be especially useful in the syntheses of novel lantibiotics. Financial support to this work was provided by MINECO (Ministerio de Economía y Competitividad, grant CTQ2013-40855-R), Gobierno de Aragon–FEDER (Grupo Aminoacidos y Peptidos E19_17R; FEDER 2014-2020 ‘Construyendo Europa desde Aragón’), and Gobierno de Aragon-FSE (Predoctoral fellowship to J.G.-V.). |
| Databáze: | OpenAIRE |
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