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 NH2-peptide resin by activating a protected aminooxyacetic acid as an active ester. Here, we have shown that its subsequent coupling to NH2-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.
Document type :
Journal articles
Complete list of metadatas

https://hal.archives-ouvertes.fr/hal-00110251
Contributor : Isabelle Frapart <>
Submitted on : Friday, October 27, 2006 - 10:12:55 AM
Last modification on : Tuesday, June 4, 2019 - 4:30:11 PM

Identifiers

Collections

Citation

Decostaire I.P., D. Lelièvre, H. Zhang, Delmas A.F.. Controlling the outcome of overacylation of N-protected aminooxyacetic during the synthesis of aminooxy-peptide for chemical ligation. Tetrahedron Letters, Elsevier, 2006, 47, pp.7057-7060. ⟨10.1016/j.tetlet.2006.07.092⟩. ⟨hal-00110251⟩

Share

Metrics

Record views

72