Biomimetic Stereoselective Formation of Methyllanthionine

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(Matrix Presented) Fmoc-(2R,3S)-3-methyl-Se-phenylselenocysleine was used for the synthesis of dehydrobutyrine (Dhb)-containing peptides. Biomimetic cyclization via Michael addition of Cys to a Dhb yielded the B-ring of the lantibiotic subtilin as a single diastereomer. The methyllanthionine product was shown to have the natural configuration by preparation of the authentic stereoisomer. The formation of a single isomer suggests that the prepeptide has a strong intrinsic preference for the stereochemistry observed in lantibiotics.

Original languageEnglish (US)
Pages (from-to)1335-1338
Number of pages4
JournalOrganic Letters
Issue number8
StatePublished - Apr 18 2002

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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