Light-Cleavable Auxiliary for Diselenide–Selenoester Ligations of Peptides and Proteins

Maximilian Schrems, Aleksandr Kravchuk, Gerhard Niederacher, Florian Exler, Claudia Bello, Christian F.W. Becker (Corresponding author)

Publications: Contribution to journalArticlePeer Reviewed

Abstract

Diselenide–selenoester ligations are increasingly used for the synthesis of proteins. Excellent ligation rates, even at low concentrations, in combination with mild and selective deselenization conditions can overcome some of the most severe challenges in chemical protein synthesis. Herein, the versatile multicomponent synthesis and application of a new ligation auxiliary that combines a photocleavable scaffold with the advantages of selenium-based ligation strategies are presented. Its use was investigated with respect to different ligation junctions and describe a novel para-methoxybenzyl deprotection reaction for the selenol moiety. The glycine-based auxiliary enabled successful synthesis of the challenging target protein G-CSF.

Original languageEnglish
Article numbere202301253
JournalChemistry - A European Journal
Volume29
Issue number46
DOIs
Publication statusPublished - 15 Aug 2023

Austrian Fields of Science 2012

  • 106002 Biochemistry
  • 104004 Chemical biology

Keywords

  • auxiliary mediated ligation
  • chemical protein synthesis
  • diselenide-selenoester ligation
  • G-CSF
  • selenocysteine protecting groups

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