Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 2, Pages 946-949Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo802415c
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- The Netherlands Organization for Scientific Research
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Lantibiotics are antimicrobial peptides containing the unique bis-amino acids lanthionine and beta-methyllanthionine. While previous syntheses of lanthionine have often involved the coupling of precursors derived from D-serine and L-Cysteine, we here report an inverted strategy whereby D-cysteine and L-serine are employed as building blocks. This approach provides for a concise preparation of tetra-ortogonally protected (2R,6S)-lanthionines while allowing convenient introduction of orthogonal protecting groups not previously incorporated into lanthionines.
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