Preparation of peptide thioesters using Fmoc strategy through hydroxyl side chain anchoring

Abstract : In the course of the chemical synthesis of human protein mitogaligin, we present here a simple method to prepare peptide thioesters using Fmoc chemistry. The hydroxyl side chain of serine was reacted with a trichloroacetimidate Wang resin to anchor it on solid phase. After peptide elongation and orthogonal unmasking of the C-terminus, the amino thioester was introduced under optimized conditions to avoid epimerization.
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Submitted on : Thursday, September 16, 2010 - 3:45:13 PM
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Dominique Lelièvre, P. Barta, Vincent Aucagne, A.F. Delmas. Preparation of peptide thioesters using Fmoc strategy through hydroxyl side chain anchoring. Tetrahedron Letters, Elsevier, 2008, 49 (25), pp.4016-4019. ⟨10.1016/j.tetlet.2008.04.087⟩. ⟨hal-00518141⟩

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