Synthesis of xylose-binding cyclic octalipopeptides burkholdine-1213 analogues. (21st December 2021)

• Record Type: Journal Article
• Authors: Sasaki, Mio; Kadowaki, Toma; Kato, Seiya; Chida, So; Yano, Shigekazu; Nosaka, Kazuto; Konno, Hiroyuki
• Is Part Of: Tetrahedron letters. Volume 87(2021)
• Publication Date: 2021-12-21
• Subjects: Antifungal -- Lipopeptide -- Burkholdine -- Xylose-bearing cyclic peptide; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2021.153542
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The synthesis of xylose-bearing cyclic octalipopeptides burkholdine-1213 analogues is described. Sugar-containing lipopeptides are generally highly amphiphilic and often exhibit potent antifungal activities, but a synthesis of a xylose-bearing burkholdine analogue has never been reported. We prepared burkholdine-1213 analogues by solution-phase macrolactamization of xylose-bearing linear peptides obtained by incorporating the bespoke Fmoc-Ser(β-O-xyloseAc3 )-OH building block into a Fmoc-solid phase peptide synthesis protocol. All analogues synthesized exhibited similar properties and moderate antifungal activities.