Carbohydrate-based surfactants

Patent metadata

Field	Value
Publication number	US-11117914-B2
Application number	US-201615358159-A
Country	US
Kind code	B2
Filing date	Nov 22, 2016
Priority date	Nov 16, 2012
Publication date	Sep 14, 2021
Grant date	Sep 14, 2021

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 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.

Assignees

• Univ Arizona

Inventors

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

Classifications

• C07F9/94

  Bismuth compounds · CPC title

• C07H15/14 Primary

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

• C07H15/04

  attached to an oxygen atom of the saccharide radical · CPC title

• C07H15/06

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

• C07F3/003

  without C-Metal linkages · CPC title