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A substrate tagging and two-step enzymatic reaction strategy for large-scale synthesis of 2,7-anhydro-sialic acid.

Authors
  • Li, Wanqing1
  • Ghosh, Tamashree1
  • Bai, Yuanyuan1
  • Santra, Abhishek1
  • Xiao, An1
  • Chen, Xi2
  • 1 Department of Chemistry, University of California, One Shields Avenue, Davis, CA, 95616, USA.
  • 2 Department of Chemistry, University of California, One Shields Avenue, Davis, CA, 95616, USA. Electronic address: [email protected]
Type
Published Article
Journal
Carbohydrate research
Publication Date
Jun 01, 2019
Volume
479
Pages
41–47
Identifiers
DOI: 10.1016/j.carres.2019.05.002
PMID: 31132641
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

A sialyltransferase acceptor tagging and two-step enzymatic reaction strategy has been developed for multigram-scale chemoenzymatic synthesis of 2,7-anhydro-N-acetylneuraminic acid (2,7-anhydro-Neu5Ac), a compound that can serve as a sole carbon source for the growth of Ruminococcus gnavus, a common human gut commensal. Different approaches of introducing hydrophobic UV-active tags to lactose as well-suited sialyltransferase acceptors have been explored and a simple two-step high-yield chemical synthetic procedure has been identified. The UV-active hydrophobic tag facilitates monitoring reaction progress and allows facile product purification by C18-cartridges. A two-step enzyme-catalyzed reaction procedure has been established to combine with C18 cartridge-based purification process for high-yield production of the desired product in multigram scales with the recycled use of chromophore-tagged lactoside starting material and sialoside intermediate. This study demonstrated an environmentally friendly highly-efficient synthetic and purification strategy for the production of 2,7-anhydro-Neu5Ac to explore its potential functions. Copyright © 2019 Elsevier Ltd. All rights reserved.

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