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

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

Fingerprint

N-Acetylneuraminic Acid
Sialyltransferases
Purification
Substrates
Ruminococcus
Lactose
Chromophores
Carbon
Monitoring
Enzymes
Growth
2,7-anhydro-N-acetylneuraminic acid

Keywords

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

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

A substrate tagging and two-step enzymatic reaction strategy for large-scale synthesis of 2,7-anhydro-sialic acid. / Li, Wanqing; Ghosh, Tamashree; Bai, Yuanyuan; Santra, Abhishek; Xiao, An; Chen, Xi.

In: Carbohydrate Research, Vol. 479, 01.06.2019, p. 41-47.

Research output: Contribution to journalArticle

Li, Wanqing ; Ghosh, Tamashree ; Bai, Yuanyuan ; Santra, Abhishek ; Xiao, An ; Chen, Xi. / A substrate tagging and two-step enzymatic reaction strategy for large-scale synthesis of 2,7-anhydro-sialic acid. In: Carbohydrate Research. 2019 ; Vol. 479. pp. 41-47.
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