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) |
|---|---|
| Pages (from-to) | 41-47 |
| Number of pages | 7 |
| Journal | Carbohydrate Research |
| Volume | 479 |
| DOIs | |
| State | Published - Jun 1 2019 |
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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 journal › Article
}
TY - JOUR
T1 - A substrate tagging and two-step enzymatic reaction strategy for large-scale synthesis of 2,7-anhydro-sialic acid
AU - Li, Wanqing
AU - Ghosh, Tamashree
AU - Bai, Yuanyuan
AU - Santra, Abhishek
AU - Xiao, An
AU - Chen, Xi
PY - 2019/6/1
Y1 - 2019/6/1
N2 - 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.
AB - 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.
KW - 2,7-Anhydro-N-Acetylneuraminic acid
KW - Chemoenzymatic synthesis
KW - Sialic acid
KW - Sialidase
KW - Sialyltransferase
KW - Substrate tagging
UR - http://www.scopus.com/inward/record.url?scp=85066046835&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85066046835&partnerID=8YFLogxK
U2 - 10.1016/j.carres.2019.05.002
DO - 10.1016/j.carres.2019.05.002
M3 - Article
C2 - 31132641
AN - SCOPUS:85066046835
VL - 479
SP - 41
EP - 47
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
ER -