Controlling the outcome of overacylation of N-protected aminooxyacetic during the synthesis of aminooxy-peptide for chemical ligation

Abstract : An aminooxy-containing peptide, the nucleophile partner for oxime ligations, is usually grafted on a NH[2]-peptide resin by activating a protected aminooxyacetic acid as an active ester. Here, we have shown that its subsequent coupling to NH[2]-peptide resin competes with the overacylation of the -NH-O- nitrogen and that the overacylation level increases with the basicity of the reaction mixture. Moreover, we found that overacylation is prevented when the COOH of the Aoa-derivatives is engaged in an amide bond.
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Submitted on : Thursday, August 30, 2007 - 11:06:46 AM
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Isidore P. Decostaire, Dominique Lelièvre, Zhang Haihui, Agnès F. Delmas. Controlling the outcome of overacylation of N-protected aminooxyacetic during the synthesis of aminooxy-peptide for chemical ligation. Tetrahedron Letters, Elsevier, 2006, 47 (39), pp.7057-7060. ⟨hal-00168750⟩

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