Carbohydrate-based surfactants

Patent metadata

Field	Value
Publication number	US-2017121362-A1
Application number	US-201615358159-A
Country	US
Kind code	A1
Filing date	Nov 22, 2016
Priority date	Nov 16, 2012
Publication date	May 4, 2017
Grant date	—

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.

First claim

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 14 or 16 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.

Assignees

• Univ Arizona

Inventors

• Pemberton Jeanne E
• Polt Robin L
• Maier Raina M
• Pacheco Ricardo Palos

Classifications

• C07H15/06

  being a hydroxyalkyl group esterified by a fatty acid · CPC title

• C07H15/14 Primary

  attached to a sulfur, selenium or tellurium atom of a saccharide radical · CPC title

• C07F9/94

  Bismuth compounds · CPC title

• C07H1/00

  Processes for the preparation of sugar derivatives · CPC title

• C07F3/003

  without C-Metal linkages · CPC title