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Method for Preparing 3,6-Anhydro-L-Galactose, And Use Thereof

a technology of anhydrolgalactose and a method of preparing it, which is applied in the field of 3, 6anhydrolgalactose, can solve the problems of low yield, easy degradation to excessive extent, and low yield of desired product, and achieves the effect of minimizing over-degradation effects and high yield

Inactive Publication Date: 2015-08-06
KOREA UNIV RES & BUSINESS FOUND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention is about a method to make 3,6-anchro-L-galactose with a high yield using enzymatic degradation. This method reduces the over-degradation effects caused by chemical treatment. Additionally, the invention also provides the use of this compound to make pharmaceutical compositions to prevent or treat skin pigmentation diseases.

Problems solved by technology

As one of monosaccharides constituting the agarooligosaccharides, 3,6-anhydro-L-galactose has problems in that it is produced as a monosaccharide with a very low yield through conventional chemical treatments, and is easily degraded to excessive extents since it has an unstable reducing end and is easily converted into hydroxymethylfurfural in the presence of a high-concentration strong acid under high-temperature reaction conditions (Jol et al (1999) Anal Biochem.
Also, although the hydrolysis using chemical treatment has an advantage in that it is readily applicable for the purpose of commercialization due to low production cost and simple treatment conditions, it has a problem in that a desired product is produced with a very low yield when specific linkages are broken to obtain the product since the chemical treatment non-specifically breaks the linkages (Chen et al (2005) Food Technol Biotechnol.

Method used

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  • Method for Preparing 3,6-Anhydro-L-Galactose, And Use Thereof
  • Method for Preparing 3,6-Anhydro-L-Galactose, And Use Thereof
  • Method for Preparing 3,6-Anhydro-L-Galactose, And Use Thereof

Examples

Experimental program
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Effect test

example 1

Hydrolysis of Agarose Using Acetic Acid

[0106]Agarose that is a representative polysaccharide constituting a sea alga was hydrolyzed with acetic acid. 5% (w / v) of agarose was reacted with 3M acetic acid at 80° C. for 70 minutes and dried to remove acetic acid. Also, acetic acid which remained after drying through a washing procedure using ethanol, and over-degradation products that were able to be produced upon hydrolysis were removed to produce an agarooligosaccharide in the form of a pure powder (FIG. 2).

example 2

Production of 3,6-Anhydro-L-Galactose Using Aga50D and sdNABH

[0107]To degrade the acid hydrolysate produced in Example 1 into monosaccharides, D-galactose and 3,6-anhydro-L-galactose, the acid hydrolysate was reacted with an exo-type disaccharide-producing enzyme, Aga50D, (see Korean Patent Publication No. 2010-0040438) to produce neoagarobiose as a reaction product.

[0108]When the reaction with Aga50D was completed, the Aga50D reaction product was reacted with an sdNABH enzyme (see Korean Patent Publication No. 2010-0108241) in order to produce the monosaccharides, D-galactose and 3,6-anhydro-L-galactose, from the neoagarobiose. The enzymatic reaction conditions were as follows: 5% (w / v) of agarooligosaccharide was dissolved in 100 mL of a 50 mM Tris-HCl buffer solution (pH 7.4), and reacted at 30° C. and 150 rpm for 3 days. The amounts of the enzymes used upon the enzymatic reaction were 10 mg and 2.5 mg for Aga50D and sdNABH, respectively (FIG. 2).

example 3

Separation and Purification Using Silica Gel Chromatography and Biogel P2 Chromatography

[0109]Chromatography was performed to separate and purify only 3,6-anhydro-L-galactose from the reaction products produced in Examples 1 and 2. The reaction products were adsorbed onto celite to form a sample in the form of powder, and subjected to silica gel chromatography that was adsorption chromatography. A solvent obtained by mixing chloroform, methanol, and water at a ratio of 78:20:2 (v / v / v) was used as a mobile phase, and the total volume of the solvent as the mobile phase was 3 L. The volume of one fraction was 20 mL, and the sample composed of a total of 150 fractions was analyzed through TLC. Among these, the fractions containing 3,6-anhydro-L-galactose were collected. Since the biogel P2 chromatography to be further performed separated materials according to the molecular weights, the fractions containing D-galactose having a molecular weight similar to 3,6-anhydro-L-galactose among t...

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Abstract

The present invention relates to a method for preparing 3,6-anhydro-L-galactose, and use thereof. More specifically, 3,6-anhydro-L-galactose, which is a monosaccharide constituting agar, is produced in a high yield through chemical and enzymatic methods, and the physiological activities thereof such as whitening, moisturizing, antioxidant, anti-inflammatory activities and the like are displayed, thereby enabling industrial use thereof.

Description

BACKGROUND[0001]1. Field of the Invention[0002]The present invention relates to 3,6-anhydro-L-galactose prepared through chemical and enzymatic methods and industrial use thereof using physiological efficacy.[0003]2. Discussion of Related Art[0004]Agar (or agarose) which is a main polysaccharide constituting a red alga is a polymer in which two monosaccharides, 3,6-anhydro-L-galactose and D-galactose, are alternately bound via α-1,3 linkage and β-1,4 linkage. It has been widely known in that an agarooligosaccharide produced by non-specifically hydrolyzing agarose using a chemical catalyst such as hydrochloric acid, sulfuric acid, and acetic acid exhibits excellent physiological activities such as antioxidant, anti-inflammatory, anti-cancer, whitening, and anti-allergic activities. Due to a variety of such physiological activities, agarooligosaccharides and neoagarobiose that are disaccharides have been widely used as functional materials in the fields of food and beauty industries.[...

Claims

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Application Information

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IPC IPC(8): A61K8/60C12P19/02A61Q19/00C12P19/14A61K31/7004A61Q19/02
CPCA61K8/60A61K31/7004A61Q19/02A61K2800/10C12P19/14C12P19/02A61Q19/007A61P17/00A61P17/16A61P29/00A61Q19/00C07H1/08C07H3/10C12Y302/01C12Y302/01159
Inventor KIM, KYOUNG HEONCHOI, IN GEOLKANG, NAM JOOYUN, EUN JULEE, SAE YOUNGKIM, JI HYEKIM, YOUNG AHKIM, BO BAEBAEK, EUN JI
Owner KOREA UNIV RES & BUSINESS FOUND
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