Carbohydrate-based surfactants

Abstract

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.

What is claimed is: 
     
         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.