Protecting-group-free glycosylation of phosphatidic acid in aqueous media

The glycosylation of unprotected carbohydrates has emerged as an area of significant interest because it obviates the need for long reaction sequences involving protecting-group manipulations. Herein, we report the one-pot synthesis of anomeric glycosyl phosphates through the condensation of unprote...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-03, Vol.21 (1), p.2138-2142
Main Authors: Kano, Koki, Ishii, Nozomi, Miyagawa, Atsushi, Takeda, Hiroaki, Hirabayashi, Yoshio, Kamiguchi, Hiroyuki, Greimel, Peter, Matsuo, Ichiro
Format: Article
Language:English
Subjects:
Aqueous solutions
Carbohydrates
Glycerol
Glycerol-3-phosphate
Glycosylation
Mass spectrometry
Mass spectroscopy
Phosphates
Phosphatidic acid
Phospholipids
Propionitrile
Stable isotopes
Stereoselectivity
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Summary:The glycosylation of unprotected carbohydrates has emerged as an area of significant interest because it obviates the need for long reaction sequences involving protecting-group manipulations. Herein, we report the one-pot synthesis of anomeric glycosyl phosphates through the condensation of unprotected carbohydrates with phospholipid derivatives while retaining high stereo- and regioselective control. The anomeric center was activated using 2-chloro-1,3-dimethylimidazolinium chloride to facilitate condensation with glycerol-3-phosphate derivatives in an aqueous solution. A water/propionitrile mixture provided superior stereoselectivity while maintaining good yields. Under these optimized conditions, the condensation of stable isotope-labeled glucose with phosphatidic acid provided efficient access to labeled glycophospholipids as an internal standard for mass spectrometry. Convenient one-pot synthesis of anomeric glycosyl phosphates by direct condensation of unprotected glucose with phospholipid derivatives in aqueous media while retaining high levels of stereoselective control.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob02173k