Synthesis of Peptides Containing Overlapping Lanthionine Bridges on the Solid Phase: An Analogue of Rings D and E of the Lantibiotic Nisin

A methodology for the solid-phase synthesis of the overlapping lanthionine bridges found in many lantibiotics has been developed. A novel Teoc/TMSE-protected lanthionine derivative has been synthesized, and this lanthionine, and an Aloc/allyl-protected lanthionine derivative, have been incorporated...

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Bibliographic Details
Published in:Organic letters 2011-08, Vol.13 (16), p.4216-4219
Main Authors: Mothia, Begum, Appleyard, Antony N, Wadman, Sjoerd, Tabor, Alethea B
Format: Article
Language:English
Subjects:
Alanine - analogs & derivatives
Alanine - chemistry
Amino Acid Sequence
Nisin - analogs & derivatives
Peptides - chemistry
Sulfides - chemistry
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Summary:A methodology for the solid-phase synthesis of the overlapping lanthionine bridges found in many lantibiotics has been developed. A novel Teoc/TMSE-protected lanthionine derivative has been synthesized, and this lanthionine, and an Aloc/allyl-protected lanthionine derivative, have been incorporated into a linear peptide using solid-phase peptide synthesis. Selective deprotection of the silyl protecting groups, followed by sequential cyclization, deprotection of the allyl protecting groups, and further cyclization, enabled the regioselective formation of an analogue of rings D and E of nisin.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201548m