Synthesis and surface-active properties of glycosyl carbamates and thioureas

Several amphiphilic glycosyl carbamates, glycosyl thiocarbamates and glycosylthioureas were prepared by addition of the anomeric hydroxyl group of acetylated glycosyl derivatives to alkyl isocyanates, or by reaction of glycosyl isothiocyanates with alcohols or amines. The solubility, critical micell...

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Bibliographic Details
Published in:Carbohydrate research 1999-09, Vol.321 (1), p.4-14
Main Authors: Prata, Carla, Mora, Nathalie, Lacombe, Jean-Michel, Maurizis, Jean-Claude, Pucci, Bernard
Format: Article
Language:English
Subjects:
Carbamates - chemical synthesis
Glycoconjugates - chemical synthesis
Magnetic Resonance Spectroscopy
Molecular Structure
N-Glycosyl carbamates
N-Glycosyl thiocarbamates
N-Glycosylthioureas
O-Glycosyl carbamates
Protein extraction
Solubility
Surface Properties
Surface Tension
Surface-Active Agents - chemical synthesis
Surfactants
Thiocarbamates - chemical synthesis
Thiourea - analogs & derivatives
Thiourea - chemical synthesis
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Summary:Several amphiphilic glycosyl carbamates, glycosyl thiocarbamates and glycosylthioureas were prepared by addition of the anomeric hydroxyl group of acetylated glycosyl derivatives to alkyl isocyanates, or by reaction of glycosyl isothiocyanates with alcohols or amines. The solubility, critical micelle concentrations and detergent efficiency for the extraction of proteins of these compounds were evaluated and compared.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(99)00161-5