GAP Peptide Synthesis through the Design of a GAP Protecting Group: An Fmoc/tBu Synthesis of Thymopentin Free from Polymers, Chromatography and Recrystallization

Cole W. Seifert, Armando Paniagua, Gabrielle A. White, Lucy Cai, Guigen Li

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

A novel method for Fmoc/tBu solution-phase peptide synthesis and the development of a new benzyl-type group-assisted purification (GAP) protecting group is reported. This GAP protecting group is utilized in place of a polymer support, facilitating C→N Fmoc peptide synthesis without chromatography or recrystallization. The GAP group can be added and removed in high yield, and was used to synthesize over 1 gram of the immunostimulant, thymopentin, in high overall yield (83 %) and purity (99 %). Fmoc/tBu solution-phase peptide synthesis and the development of a new benzyl-type group-assisted purification (GAP) protecting group is reported. This new GAP protecting group replaces a polymer support, facilitating C→N Fmoc peptide synthesis without chromatography or recrystallization. Over 1 gram of the immunostimulant, thymopentin, was synthesized in high overall yield (83 %) and purity (99 %).

Original languageEnglish
Pages (from-to)1714-1719
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number9
DOIs
StatePublished - Mar 1 2016

Keywords

  • Amino acids
  • GAP chemistry
  • Peptides
  • Protecting groups
  • Synthetic methods

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