Cysteine-Free Intramolecular Ligation of N -Sulfanylethylanilide Peptide Using 4-Mercaptobenzylphosphonic Acid: Synthesis of Cyclic Peptide Trichamide
SYNLETT(2017)
Abstract
An N-sulfanylethylanilide (SEAlide)-based ligation was developed for the preparation of trichamide, a thiazole-containing cyclic peptide isolated from bloom-forming cyanobacterium Trichodesmium erythraeum. In this cysteine-free ligation, 4-mercaptobenzylphosphonic acid (MBPA) functions as a dual promoter both for the N-S acyl-transfer-mediated activation of the SEAlide unit and for subsequent ligation. Furthermore, we established a high-yielding route to enantiomerically pure thiazole amino acids using a one-pot Hantzsch process.
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Key words
peptides,thioester,N-S acyl transfer,chemical ligation,cyclic peptides
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