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 trisaccharides and a thiol or amine derivative thereof, wherein said monosaccharide is selected from the group consisting of allose, altrose, arabinose, fructose, galactose, gulose, idose, lyxose, psicose, rhamnose, ribose, ribulose, sorbose, tagatose, talose, xylose, xylulose, and a thiol derivative thereof; and
B is selected from a moiety selected from the group consisting of the formula: —(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 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.