Native chemical ligation at a base-labile 4-mercaptobutyrate (cas 13095-66-4) Nα-auxiliary

Add time:09/25/2019    Source:infona.pl

Native chemical ligation (NCL) proceeds via a S–N acyl shift and, therefore, requires N-terminal cysteine. Nα-auxiliaries have long been used to enable NCL beyond cysteine. However, the reversibility of the S–N acyl shift under the acidic conditions used to remove the commonly applied N-benzyl auxiliaries limits the scope of this reaction. Herein, we introduce a new class of Nα-auxiliary which is designed for removal under mild basic conditions. The 3-N-linked 4-mercaptobutyrate (cas 13095-66-4) auxiliary is readily synthesized in a single step and enables introduction on solid phase by means of reductive amination. The usefulness of the new auxiliary was demonstrated in the synthesis of the anti-microbial C-terminal domain of Dermicidine-1L.

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