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Efficient preparation of Fmoc-aminoacyl-N-ethylcysteine unit, a key device for the synthesis of peptidethioesters
Hironobu Hojo,Hajime Kobayashi,Risa Ubagai,Yuya Asahina,Yuko Nakahara,Hidekazu Katayama,Yukishige Ito,Yoshiaki Nakahara
Organic & Biomolecular Chemistry Pub Date : 07/08/2011 00:00:00 , DOI:10.1039/C1OB05831B
Abstract

The synthesis of Fmoc-aminoacyl-N-ethyl-S-triphenylmethylcysteine, an N- to S-acyl migratory device for the preparation of peptide thioesters by Fmoc-SPPS (solid-phase peptide synthesis) is described. Condensation of Fmoc-aminoacyl pentafluorophenyl ester and N-ethyl-S-triphenylmethylcysteine was efficiently performed in the presence of HOOBt (3-hydroxy-3,4-dihydro-4-oxo-1,2,3-benzotriazine) in DMF. A small amount of diastereomer yielded during the reaction was easily separated by HPLC purification and the highly pure devices were obtained for most of the proteinogenic amino acids.

Graphical abstract: Efficient preparation of Fmoc-aminoacyl-N-ethylcysteine unit, a key device for the synthesis of peptide thioesters
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