Peptide thioester preparation based on an N-S acyl shift reaction mediated by a thiol ligation auxiliary |
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Authors: | Toru Kawakami,Ken&rsquo ichiroh Nakamura,Saburo Aimoto |
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Affiliation: | a Institute for Protein Research, Osaka University, 3-2 Yamadaoka, Suita, Osaka 565-0871, Japan b Bachem Holdings AG, Hauptstrasse 144, CH-4416 Bubendorf, Switzerland |
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Abstract: | Formation of peptide thioesters, based on an N to S acyl shift mediated by an auxiliary, N-4,5-dimethoxy-2-mercaptobenzyl (Dmmb) group, under acidic conditions, is described. The protected peptide was assembled on a hydroxymethylphenylacetamidomethyl resin via an N-Dmmb-amino acid residue according to standard Fmoc solid-phase peptide synthesis following treatment with trifluoroacetic acid. The peptide α-thioester was released from the resin by reaction with 2-mercaptoethanesulfonic acid in the presence of N,N-diisopropylethylamine. |
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Keywords: | Fmoc solid-phase peptide synthesis N-S Acyl shift Peptide thioester Thioester-producing auxiliary |
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