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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 19
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Original Articles

Synthesis of Hydroxymethyl Side-Chained α-Aminoxy Diamide

, , &
Pages 2815-2821 | Received 27 Mar 2009, Published online: 25 Aug 2010
 

Abstract

Unnatural polar α-aminoxy acid residue with proteingenous hydroxymethyl side chain, a building block of the peptidomimetic foldamer of α-aminoxy peptide, was synthesized starting from natural amino acid L-serine. The starting material, L-serine, undergoes a reaction sequence to produce compound 1 in three steps: (1) the neighboring carboxyl group participates in diazotization/bromination to transform the amino group to a bromo group, (2) the C-terminal carboxyl group is protected, and (3) bromide is SN2-displaced by N-hydroxyl phthalimide to introduce a N‒O bond. After several conventional deprotection/coupling reactions, compound 1 is easily transformed to an α-aminoxy diamide, which can be widely used in peptidomimetics design.

ACKNOWLEDGMENTS

This work was supported by the National Natural Science Foundation of China (Project No. 20202001), Fok Ying Tung Education Foundation (Project No. 94023), and Fudan University. D.-W. Z. thanks Fudan University for the Century Star Award.

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