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Diastereopure synthesis of novel cyclohexane-ring-based constrained lanthionine and α-methyllanthionine through an SN2 reaction with a β-bromoalanine as a key step

AuthorsGracia-Vitoria, Jaime; Carretero, Ángel; Cativiela, Carlos
Issue Date2020
CitationSynlett 31(04): 383-387 (2020)
AbstractHere 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.
Publisher version (URL)https://doi.org/10.1055/s-0039-1690790
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