Crystalline maltotetraosyl glucoside, and its production and use

• US 5,922,691 A
• Filed: 04/07/1997
• Issued: 07/13/1999
• Est. Priority Date: 03/01/1994
• Status: Expired due to Fees

• Current Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kaguku Kenkyujo
• Original Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kaguku Kenkyujo
• Inventors: Miyake, Toshio, Sugimoto, Toshiyuki, Shibuya, Takashi, Mandai, Takahiko
• Primary Examiner(s): FONDA, KATHLEEN KAHLER
• Application Number:
  US08/826,765
• Time in Patent Office: 827 Days
• Field of Search: 435/95, 435/96, 435/97, 435/99, 435/100, 435/101, 435/200, 435/201, 435/202, 536/102, 536/123.1, 536/124, 514/54, 514/60
• US Class Current: 514/54
• CPC Class Codes: A23G 1/40 characterised by the carbohydrates used, e.g. polysaccharides containing dairy products A23G1/46
• CPC Class Codes: A23G 3/42 characterised by the carbohydrates used, e.g. polysaccharides containing dairy products A23G3/46
• CPC Class Codes: A23G 4/10 characterised by the carbohydrates used, e.g. polysaccharides containing dairy products A23G4/16
• CPC Class Codes: A61K 8/60 Sugars; Derivatives thereof
• CPC Class Codes: A61K 8/602 Glycosides, e.g. rutin
• CPC Class Codes: A61Q 11/00 Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
• CPC Class Codes: A61Q 17/04 Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 19/02 for chemically bleaching or whitening the skin
• CPC Class Codes: C07H 3/06 Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
• CPC Class Codes: C12N 9/1074 Cyclomaltodextrin glucanotransferase (2.4.1.19)
• CPC Class Codes: C12P 19/14 produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase , e.g. by cellulase, hemicellulase
• CPC Class Codes: C12P 19/18 produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
• CPC Class Codes: C12Y 204/01019 Cyclomaltodextrin glucanotransferase (2.4.1.19)

Abstract

Novel crystalline maltotetraosyl glucoside is obtained by crystallizing maltotetraosyl glucoside from a solution of maltotetraosyl glucoside, prepared by either exposing an aqueous solution of maltopentaose to the action of a non-reducing saccharide-forming enzyme or an aqueous solution which contains trehalose or a non-reducing saccharide to the action of cyclomaltodextrin glucanotransferase. The crystalline maltotetraosyl glucoside has non-hygroscopicity, non-reducibility, superior solubility, less fermentability, and other satisfactory properties of stabilizing oligopeptides and biologically-substances as well as preventing retrogradation of amylaceous substances. These features render the crystalline maltotetraosyl glucoside very useful in various compositions including foods, beverages, cosmetics, pharmaceuticals and shaped bodies.

Claims

1. A non-reducing crystalline maltotetraosyl glucoside selected from the group consisting of a hydrous crystalline maltotetraosyl glucoside and an anhydrous crystalline maltotetraosyl glucoside, wherein:

(a) said hydrous crystalline maltotetraosyl glucoside has the largest diffraction angles (2θ

) of 12.6°

, 21.3°

, 22.1°

, and 22.8°

on powder X-ray diffraction analysis, exhibits two endothermic peaks at 170 to 172°

C. and 230 to 233°

C. when measured by a differential scanning calorimeter and a purity of at least 99.5; and

(b) said anhydrous crystalline maltotetraosyl glucoside has the largest diffraction angles (2θ

) of 12.7°

, 13.7°

, 18.8°

, and 23.2°

on powder X-ray diffraction analysis, exhibits one endothermic peak at 230 to 233°

C. when measured by a differential scanning calorimeter, and a purity of at least 99.5%.

2. A process for preparing crystalline maltotetraosyl glucoside of claim 1, which comprises:

(a) crystallizing maltotetraosyl glucoside from a solution of maltotetraosyl glucoside; and

(b) recovering the crystalline maltotetraosyl glucoside.

3. The process of claim 2, wherein said maltotetraosyl glucoside is prepared by exposing an aqueous solution of maltopentaose to the action of a non-reducing saccharide-forming enzyme, or exposing an aqueous solution which contains trehalose and amylaceous substance or which contains a non-reducing saccharide to the action of cyclomaltodextrin glucanotransferase.

4. The process of claim 3, wherein said solution of maltopentaose is prepared by exposing amylaceous substance to the action of α

-amylase or a mixture of α

-amylase and a starch debranching enzyme.

5. The process of claim 3, wherein said non-reducing saccharide-forming enzyme is capable of forming a non-reducing saccharide from a reducing partial starch hydrolysate.

6. The process of claim 3, wherein said non-reducing saccharide has a trehalose structure as an end unit.

7. The process of claim 5, wherein said non-reducing saccharide has a trehalose structure as an end unit.

8. The process of claim 5, wherein said reducing partial starch hydrolysate has a glucose polymerization degree of 3 or higher.

9. A process for preparing crystalline maltotetraosyl glucoside of claim 1, which comprises:

(a) alkali-treating an aqueous solution of maltotetraosyl glucoside; and

(b) applying the resultant solution to a chromatography to obtain a fraction which is rich in the maltotetraosyl glucoside; and

(c) concentrating and crystallizing the fraction; and

(d) recovering the crystalline maltotetraosyl glucoside.

10. The process of claim 9, wherein said solution of maltotetraosyl glucoside is obtained by exposing an aqueous solution of maltopentaose to the action of a non-reducing saccharide-forming enzyme, or exposing an aqueous solution which contains trehalose and amylaceous substances or which contains a non-reducing saccharide to the action of cyclomaltodextrin glucanotransferase.

11. The process of claim 10, wherein said solution of maltopentaose is prepared by exposing amylaceous substance to the action of α

-amylase or a mixture of α

-amylase and a starch debranching enzyme.

12. The process of claim 10, wherein said non-reducing saccharide-forming enzyme is capable of forming a non-reducing saccharide from a reducing partial starch hydrolysate.

13. The process of claim 10, wherein said non-reducing saccharide has a trehalose structure as an end unit.

14. A composition which contains a crystalline maltotetraosyl glucoside of claim 1 and a filler, vehicle, or binder.

15. The composition of claim 14, wherein said composition contains said crystalline maltotetraosyl glucoside in an amount of 0.1 w/w % or more, on a dry solid basis.

16. The composition of claim 14, wherein said composition is in the form of a food, beverage, cosmetic, pharmaceutical or shaped body.

17. A process for preparing a composition containing a crystalline maltotetraosyl glucoside, which comprises a step of incorporating said crystalline maltotetraosyl glucoside into a material for a product selected from the group consisting of foods, beverages, cosmetics, pharmaceuticals and shaped bodies.

18. The process of claim 17, wherein said composition contains said crystalline maltotetraosyl glucoside in an amount of 0.1 w/w % or more, on a dry solid basis.

19. The process of claim 17, wherein said composition is in the form of a food, beverage, cosmetic, pharmaceutical or shaped body.