Section 33
Chapter 32,927

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

Lelievre, D.; Barta, P.; Aucagne, V.; Delmas, A., F.

Tetrahedron Letters 49(25): 4016-4019


ISSN/ISBN: 0040-4039
DOI: 10.1016/j.tetlet.2008.04.087
Accession: 032926421

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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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