Synthesis of nonproteinogenic amino acids to probe lantibiotic biosynthesis

Xingang Zhang, Weijuan Ni, Wilfred A. Van Der Donk

Research output: Contribution to journalArticlepeer-review


The synthesis of six nonproteinogenic amino acids appropriately protected for Fmoc-based solid-phase peptide synthesis is described. These amino acids are (2S,3A)-vinylthreonine, (2S)-(E)-2-amino-5-fluoro-pent-3-enoic acid (fluoroallylglycine), (S)-β2-homoserine, (S) and CR)-β3-homocysteine, and (2R,3R)-methylcysteine. Once incorporated into peptides, these compounds were envisioned to serve as alternative substrates for the lantibiotic synthases that dehydrate serine and threonine residues in their peptide substrates and catalyze the subsequent intramolecular Michael-type addition of cysteines to the dehydroamino acids.

Original languageEnglish (US)
Pages (from-to)6685-6692
Number of pages8
JournalJournal of Organic Chemistry
Issue number17
StatePublished - Aug 19 2005

ASJC Scopus subject areas

  • Organic Chemistry


Dive into the research topics of 'Synthesis of nonproteinogenic amino acids to probe lantibiotic biosynthesis'. Together they form a unique fingerprint.

Cite this