Accelerated Solid Phase Glycan Synthesis: ASGS

Yasmeen Bakhatan, Israel Alshanski, Chieh Kai Chan, Wei Chih Lo, Po Wei Lu, Pin Hsuan Liao, Cheng Chung Wang*, Mattan Hurevich*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Solid phase synthesis is the most dominant approach for the preparation of biological oligomers as it enables the introduction of monomers iteratively. Accelerated solid phase synthesis of biological oligomers is crucial for chemical biology, but its application to the synthesis of oligosaccharides is not trivial. Solid-phase oligosaccharide assembly is a slow process performed in a variety of conditions and temperatures, requires an inert gas atmosphere, and demands high excess of glycosyl donors. The process is done in special synthesizers and poor mixing of the solid support increases the risk of diffusion-independent hydrolysis of the activated donors. High shear stirring is a new way to accelerate solid phase synthesis. The efficient mixing ensures that reactive intermediates can diffuse faster to the solid support thereby increasing the kinetics of the reactions. We report here a stirring-based accelerated solid-phase oligosaccharide synthesis. We harnessed high shear mixing to perform diffusion-dependent glycosylation in a short reaction time. We minimized the use of glycosyl donors and the need to use an inert atmosphere. We showed that by tailoring the deprotection and glycosylation conditions to the same temperature, assembly steps are performed continuously, and full glycosylation cycles are completed in minutes.

Original languageAmerican English
Article numbere202300897
JournalChemistry - A European Journal
Volume29
Issue number38
DOIs
StatePublished - 6 Jul 2023

Bibliographical note

Publisher Copyright:
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

Keywords

  • diffusion
  • glycosylation
  • mixing
  • oligosaccharides
  • solid-phase synthesis

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