Synthesis of Sucrose-Based Surfactants Through Regioselective Sulfonation of Acylsucrose and the Nucleophilic Opening of a Sucrose Cyclic Sulfate

No Thumbnail Available
Authors
Bazin, H.G.
Polat, T.
Linhardt, Robert J.
Issue Date
1998-05-01
Type
Article
Language
ENG
Keywords
Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
Research Projects
Organizational Units
Journal Issue
Alternative Title
Abstract
Synthesis of a new class of anionic and amphoteric sucrose-based surfactants is described. Direct sulfonation of 6-O-acylsucrose using the pyridine–sulfur trioxide complex led to a mixture of the regioisomeric monosulfates, 6-O-acyl-4′–O-sulfosucrose and 6-O-acyl-1′-O-sulfosucrose, while sulfonation of 1′-O-acylsucrose afforded a mixture of 1′-O-acyl-6′-O-sulfosucrose and 1′-O-acyl-6-O-sulfosucrose. The ratio of regioisomers ranged from 4.7:1.0 to 7.5:1.0, depending on reaction time and the size of the fatty acyl chain. The regiospecific synthesis of 6-O-acyl-4-O-sulfosucrose derivatives was accomplished by nucleophilic substitution of the sucrose 4,6-cyclic sulfate using various fatty acids. The amphoteric 6-alkylamino-6-deoxy-4-O-sulfosucrose surfactants were also synthesized by nucleophilic substitution of the sucrose cyclic sulfate by different fatty amines. All the newly synthesized sucrose-based surfactants displayed excellent surface-active properties.
Description
Carbohydrate Research, 309, 189-205
Note : if this item contains full text it may be a preprint, author manuscript, or a Gold OA copy that permits redistribution with a license such as CC BY. The final version is available through the publisher’s platform.
Full Citation
Synthesis of Sucrose-Based Surfactants Through RegioselectiveSulfonation of Acylsucrose and the Nucleophilic Opening of a Sucrose CyclicSulfate, H.G. Bazin, T. Polat, R.J. Linhardt, Carbohydrate Research,309,189-205, 1998.
Publisher
Terms of Use
Journal
Volume
Issue
PubMed ID
DOI
ISSN
86215
EISSN