Mercapto-functionalized polyhedral oligomeric silsesquioxane as a soluble support for the synthesis of peptide thioesters. (23rd November 2021)

• Record Type: Journal Article
• Authors: Perry, Kimberly; Sui, Binglin; Li, Yangmei
• Is Part Of: Tetrahedron letters. Volume 85(2021)
• Publication Date: 2021-11-23
• Subjects: Soluble support -- Polyhedral oligomeric silsesquioxane -- Thioester -- Peptide-based therapeutics -- Scale-up synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2021.153483
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The revival of peptide-based drugs has led to the increasing demand for the development of large-scale synthesis of these complex molecules. To meet this demand, the use of mercapto-functionalized polyhedral oligomeric silsesquioxane (POSS-SH) as a soluble support for the synthesis of a model pentapeptide POSS-thioester is reported. The synthetic process provided a total yield of 62% for the pentapeptide POSS-thioester and the 1 H NMR spectra validated the high purity of the products. The successful synthesis of the pentapeptide POSS-thioester with high yield and purity provides a promising way to the scale-up chemical synthesis of peptide thioesters, peptides, peptide amides, cyclic peptides, and even proteins.