Synthesis of Nonproteinogenic Amino Acids To Probe Lantibiotic Biosynthesis

The synthesis of six nonproteinogenic amino acids appropriately protected for Fmoc-based solid-phase peptide synthesis is described. These amino acids are (2S,3R)-vinylthreonine, (2S)-(E)-2-amino-5-fluoro-pent-3-enoic acid (fluoroallylglycine), (S)-β2-homoserine, (S) and (R)-β3-homocysteine, and (2R...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-08, Vol.70 (17), p.6685-6692
Main Authors: Zhang, Xingang, Ni, Weijuan, van der Donk, Wilfred A
Format: Article
Language:English
Subjects:
Amino Acids - chemical synthesis
Bacteriocins - biosynthesis
Chemistry
Exact sciences and technology
Magnetic Resonance Spectroscopy
Molecular Probes
Organic chemistry
Peptides
Preparations and properties
Spectrometry, Mass, Electrospray Ionization
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Summary:The synthesis of six nonproteinogenic amino acids appropriately protected for Fmoc-based solid-phase peptide synthesis is described. These amino acids are (2S,3R)-vinylthreonine, (2S)-(E)-2-amino-5-fluoro-pent-3-enoic acid (fluoroallylglycine), (S)-β2-homoserine, (S) and (R)-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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo051182o