Chemical Synthesis of Glycopeptides containing l-Arabinosylated Hydroxyproline and Sulfated Tyrosine

Org Lett. 2023 Mar 24;25(11):1907-1911. doi: 10.1021/acs.orglett.3c00411. Epub 2023 Mar 14.

Abstract

Post-translationally modified peptides are important regulating molecules for living organisms. Here, we report the stereoselective total synthesis of β-1,2-linked l-arabinosylated Fmoc-protected hydroxyproline building blocks and their incorporation, together with sulfated tyrosine and hydroxyproline, into the plant peptide hormone PSY1. Clean glycopeptides were obtained by performing acetyl removal from the l-arabinose groups prior to deprotection of the neopentyl-protected sulfated tyrosine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycopeptides* / chemistry
  • Hydroxyproline
  • Peptides / chemistry
  • Sulfates / chemistry
  • Tyrosine* / chemistry

Substances

  • Glycopeptides
  • Tyrosine
  • Hydroxyproline
  • Sulfates
  • Peptides