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 language | English (US) |
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Pages (from-to) | 41-47 |
Number of pages | 7 |
Journal | Carbohydrate Research |
Volume | 479 |
DOIs | |
State | Published - 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