1017239-39-2Relevant academic research and scientific papers
A novel protecting/activating strategy for β-hydroxy acids and its use in convergent peptide synthesis
Spengler, Jan,Ruiz-Rodriguez, Javier,Yraola, Francesc,Royo, Miriam,Winter, Manfred,Burger, Klaus,Albericio, Fernando
, p. 2311 - 2314 (2008/09/19)
(Chemical Equation Presented) β-Hydroxy acids were reacted with hexafluoroacetone and carbodiimides to give carboxy-activated six-membered lactones in good yields. On reaction with amines, the corresponding amides were obtained. We demonstrate the following applications of this protecting/ activating strategy: preparation of carboxamides in solution and on solid phase (both normal and reverse mode); recovery and reuse of the excess material in solid-phase synthesis; and convergent solid-phase peptide synthesis (CSPPS) with peptide segments bearing C-terminal Ser or Thr with very low levels of epimerization (1%, HPLC).
