Ethoxyethylidene protecting group prevents N-overacylation in aminooxy peptide synthesis |
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Authors: | Vincent Dulé ry,Pascal Dumy |
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Affiliation: | Département de Chimie Moléculaire, UMR-CNRS 5250 ICMG FR 2607, Université Joseph Fourier, 38041 Grenoble Cedex 9, France |
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Abstract: | We report herein an improved synthetic route for the preparation of homogenous aminooxy peptides suitable for oxime ligation. Aminooxyacetic acid (Aoa) was protected with 1-ethoxyethylidene group (Eei) then incorporated either using PyBOP or as N-hydroxysuccinimidyl ester at N-terminal end or at a lysine side chain into model peptides in solution and on solid support. Due to the Eei protecting group, these new reagents prevent the N-overacylation side reaction in comparison with Boc-Aoa derivatives. Subsequent deprotection under mild acidic conditions gave the corresponding pure aminooxylated peptides. |
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