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dc.contributor.authorBazin, H.G.
dc.contributor.authorPolat, T.
dc.contributor.authorLinhardt, Robert J.
dc.date1998
dc.date.accessioned2022-06-27T16:21:52Z
dc.date.available2022-06-27T16:21:52Z
dc.date.issued1998-05-01
dc.identifier.citationSynthesis 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.
dc.identifier.issn86215
dc.identifier.urihttps://doi.org/10.1016/S0008-6215(98)00121-9
dc.identifier.urihttps://hdl.handle.net/20.500.13015/5899
dc.descriptionCarbohydrate Research, 309, 189-205
dc.descriptionNote : 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.
dc.description.abstractSynthesis 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.
dc.description.urihttps://login.libproxy.rpi.edu/login?url=https://doi.org/10.1016/S0008-6215(98)00121-9
dc.languageen_US
dc.language.isoENG
dc.relation.ispartofThe Linhardt Research Labs Online Collection
dc.relation.ispartofRensselaer Polytechnic Institute, Troy, NY
dc.relation.ispartofCarbohydrate Research
dc.relation.urihttps://harc.rpi.edu/
dc.subjectBiology
dc.subjectChemistry and chemical biology
dc.subjectChemical and biological engineering
dc.subjectBiomedical engineering
dc.titleSynthesis of Sucrose-Based Surfactants Through Regioselective Sulfonation of Acylsucrose and the Nucleophilic Opening of a Sucrose Cyclic Sulfate
dc.typeArticle
dcterms.accessRightshttps://login.libproxy.rpi.edu/login?url=https://doi.org/10.1016/S0008-6215(98)00121-9
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dcterms.isVersionOfhttps://doi.org/10.1016/S0008-6215(98)00121-9
dc.rights.holderIn Copyright : this Item is protected by copyright and/or related rights. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s). https://rightsstatements.org/page/InC/1.0/
dc.creator.identifierhttps://orcid.org/0000-0003-2219-5833
dc.relation.departmentThe Linhardt Research Labs.
dc.relation.departmentThe Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)
rpi.description.pages189-205
rpi.description.volume309


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