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

Wanqing Li, Tamashree Ghosh, Yuanyuan Bai, Abhishek Santra, An Xiao, Xi Chen

Research output: Contribution to journalArticle

1 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)41-47
Number of pages7
JournalCarbohydrate Research
Volume479
DOIs
StatePublished - Jun 1 2019

Keywords

  • 2,7-Anhydro-N-Acetylneuraminic acid
  • Chemoenzymatic synthesis
  • Sialic acid
  • Sialidase
  • Sialyltransferase
  • Substrate tagging

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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