|کد مقاله||کد نشریه||سال انتشار||مقاله انگلیسی||ترجمه فارسی||نسخه تمام متن|
|1358569||981349||2016||4 صفحه PDF||سفارش دهید||دانلود رایگان|
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 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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Journal: Bioorganic & Medicinal Chemistry Letters - Volume 26, Issue 5, 1 March 2016, Pages 1434–1437