Improved synthesis of glycosylamines and a straightforward preparation of N-acylglycosylamines as carbohydrate-based detergents.
D-Glucose, D-galactose, lactose, cellobiose, and maltose yield quantitatively the corresponding glycosylamine when treated at 42 degrees C for 36 h with a commercial aqueous solution of ammonia in the presence of one equivalent of ammonium hydrogen carbonate. After lyophilisation, the residue (i.e., the pure glucosylamine) was dissolved in a mixture of ethanol and water, and treated with acyl chlorides to afford in a few minutes N-acylglucosylamines. Micellar properties of these amphiphilic derivatives were determined.
Lubineau
A
A
Institut de Chimie Moléculaire, CNRS UA 462, Université de Paris-Sud, Orsay, France.
Augé
J
J
Drouillat
B
B
D002240:Carbohydrate Sequence; D003902:Detergents / Q000138:chemical synthesis*; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D008823:Micelles; D008969:Molecular Sequence Data
D003902:Detergents; D008823:Micelles; D005944:Glucosamine