CARBOHYDRATE-BASED SURFACTANTS
The present invention provides carbohydrate-based surfactants and methods for producing the same. Methods for producing carbohydrate-based surfactants include using a glycosylation promoter to link a carbohydrate or its derivative to a hydrophobic compound.
1 . A carbohydrate-based surfactant of the formula:
A-B
wherein
A is selected from the group consisting of a monosaccharide, a disaccharide, a trisaccharide and a derivative thereof, and
B is selected from a moiety selected from the group consisting of the formula: —(CH 2 ) 2 CO 2 R z , —(CH 2 ) 2 C(═O)O(CH 2 ) 2 CO 2 R z ,
wherein
each of Y is independently selected from the group consisting of hydrogen, ethylenyl, ethynyl, halide, —SH, —NH 2 , and —CO 2 R s ;
R s is hydrogen or alkyl;
R z is hydrogen, alkyl, benzyl, or a carboxylic acid protecting group;
x is an integer from 5 to 30;
a is an integer from 2 to 18;
b is an integer from 2 to 18; and
* is a chiral center.
2 . The carbohydrate-based surfactant according to claim 1 , wherein A is a monosaccharide or a thiol derivative thereof.
3 . The carbohydrate-based surfactant according to claim 2 , wherein B is attached to the hydroxyl group of the anomeric carbon or a thiol derivative thereof of said monosaccharide.
4 . The carbohydrate-based surfactant according to claim 2 , wherein said monosaccharide is selected from the group consisting of glucose, galactose, rhamnose, arabinose, xylose, fucose and a thiol derivative thereof.
5 . The carbohydrate-based surfactant according to claim 1 , wherein A is a disaccharide or a thiol derivative thereof.
6 . The carbohydrate-based surfactant according to claim 5 , wherein said disaccharide comprises 1→4 or 1→6 linkage between two monosaccharides.
7 . The carbohydrate-based surfactant according to claim 5 , wherein said disaccharide is selected from the group consisting of lactose, maltose, melibiose, cellobiose, rutinose, and a thiol derivative thereof.
8 . The carbohydrate-based surfactant according to claim 1 , wherein said A is a trisaccharide or a thiol derivative thereof.
9 . The carbohydrate-based surfactant according to claim 8 , wherein said trisaccharide is maltotriose or a thiol derivative thereof.
10 . The carbohydrate-based surfactant according to claim 1 , wherein B is a moiety of the formula:
wherein Y, R z , x and * are as defined in claim 1 .
11 . The carbohydrate-based surfactant according to claim 10 , wherein x is 6, 10, 12 or 14.
12 . The carbohydrate-based surfactant according to claim 1 , wherein B is a moiety of the formula:
wherein Y, R z , a, b and * are as defined in claim 1 .
13 . The carbohydrate-based surfactant according to claim 12 , wherein a is 2, 6, 10, 12 or 14; and b is 2, 4, 6, 8, 10, 12 or 14.
14 . The carbohydrate-based surfactant according to claim 1 , wherein B is C 9 or C 10 alkyl.
15 . The carbohydrate-based surfactant according to claim 1 , wherein B is C 6 -C 30 hydrocarbon.
16 . The carbohydrate-based surfactant according to claim 15 , wherein B is dodecyl.