IP Library Granted Patent US 12,644,142
Granted Patent B2
US 12,644,142 · App. 17/766,405 · Granted Jun 2, 2026

Sugar composition containing cyclic tetrasaccharide, use thereof, and production method therefor

Inventors: Akiko Yasuda (Okayama, JP); Manabu Miyata (Okayama, JP); Takuo Yamamoto (Okayama, JP); Akiko Mizote (Okayama, JP); Hitoshi Mitsuzumi (Okayama, JP)
Assignee: NAGASE VIITA CO., LTD.
C12P19/16A23L29/30C07H3/06C12N9/1074C12N9/2428C12N9/2457C12P19/14C12Y302/0102
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Quick Facts
Patent No.
US 12,644,142
App. No.
17/766,405
Granted
Jun 2, 2026
Kind
B2
Abstract

The present invention aims to provide a saccharide composition suitable for a cyclic-tetrasaccharide-containing starch syrup which has low viscosity, low water activity, low coloration property, and low calorie content, and which is unlikely to cause precipitation of crystals of saccharides during storage, and to provide a use of the composition and a production method for the composition. The object is achieved by providing a cyclic-tetrasaccharide-containing saccharide composition having the following characteristics (1) to (3): (1) the saccharide composition includes a branched cyclic tetrasaccharide in addition to the cyclic tetrasaccharide, wherein the content of the cyclic tetrasaccharide with respect to the total solid content of the saccharide composition obtained by allowing glucoamylase and α-glucosidase to act on the above saccharide composition is 38% by mass or higher, on a dry solid basis; (2) the ratio of α-1,4-linked glucose in the total glucose residues constituting the saccharide composition in methylation analysis is over 9% and 15% or lower, and (3) the ratio of α-1,4,6-linked glucose in the total glucose residues constituting the saccharide composition in methylation analysis is less than 6%; and providing a use of the composition and a production method for the composition.

Claims (61)

1 . A saccharide composition comprising:

(a) a cyclic tetrasaccharide represented by cyclo {→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→}, and

(b) a branched cyclic tetrasaccharide comprising one or more glucose molecules linked to the cyclic tetrasaccharide,

wherein said saccharide composition has the following characteristics (1) to (3):

(1) after allowing glucoamylase and α-glucosidase to act on said saccharide composition, the content of cyclic tetrasaccharide with respect to the total solid content of the resulting saccharide composition is 38% by mass or higher, on a dry solid basis;

(2) the ratio of α-1,4-linked glucose in the total glucose residues constituting the saccharide composition in methylation analysis is over 9% and 15% or lower, and

(3) the ratio of α-1,4,6-linked glucose in the total glucose residues constituting the saccharide composition in methylation analysis is less than 6%.

2 . The saccharide composition according to claim 1 , further having the following characteristic (4):

(4) the content of the cyclic tetrasaccharide with respect to the total solid content in the saccharide composition is 25% by mass or higher, on a dry solid basis.

3 . The saccharide composition according to claim 2 , further having the following characteristics (5) and (6):

(5) the saccharide composition comprises carbohydrate with a degree of polymerization of 1 or 2 at a total content of 16% by mass or lower, on a dry solid basis with respect to the total solid content; and

(6) the saccharide composition comprises carbohydrate with a degree of polymerization of 4 to 13 other than the cyclic tetrasaccharide and the branched cyclic tetrasaccharide comprising one or two glucose molecules linked to the cyclic tetrasaccharide, at a total content of over 37% by mass, on a dry solid basis with respect to the total solid content.

4 . The saccharide composition according to claim 1 , wherein an aqueous solution of the saccharide composition at a solid concentration of 73% by mass has a viscosity of 35 Pa·s or lower at 15° C.

5 . The saccharide composition according to claim 1 , wherein an aqueous solution of the saccharide composition at a solid concentration of 73% by mass has a water activity of less than 0.88.

6 . A reduced product of the saccharide composition according to claim 1 .

7 . A composition comprising: the saccharide composition according to claim 1 and/or a reduced product of the saccharide composition according to claim 1 ; and another material.

8 . An aqueous solution of (i) the saccharide composition according to claim 1 , (ii) a reduced product of the saccharide composition according to claim 1 , or (iii) composition comprising (i) and/or (ii) and another material.

9 . The composition according to claim 8 , having a solid concentration of 70% by mass or higher.

10 . The saccharide composition according to claim 1 , as a food, food material, cosmetic material, quasi-drug material, pharmaceutical material, livestock-feed material, fish-feed material, or fertilizer material.

11 . A method of producing the saccharide composition according to claim 1 , comprising the steps of:

allowing α-isomaltosylglucosaccharide-forming enzyme and α-isomaltosyltransferase to act on a partial starch hydrolyzate, to produce the cyclic tetrasaccharide (Step 1); and

purifying and collecting the resulting enzyme reaction product containing the cyclic tetrasaccharide (Step 2);

wherein

a starch debranching enzyme is also allowed to act in Step 1;

with the proviso that the method includes no step of allowing an exo-type amylase having actions of producing monosaccharides or disaccharides to act.

12 . The method of producing the saccharide composition according to claim 11 , wherein isoamylase or pullulanase is used as the starch debranching enzyme.

13 . The method of producing the saccharide composition according to claim 11 , wherein cyclomaltodextrin glucanotransferase is also allowed to act in Step 1.

14 . A method of producing the reduced product of the saccharide composition according to claim 6 , comprising the steps of:

allowing α-isomaltosylglucosaccharide-forming enzyme and α-isomaltosyltransferase to act on a partial starch hydrolyzate, to produce the cyclic tetrasaccharide (Step 1); and

purifying and collecting the resulting enzyme reaction product containing the cyclic tetrasaccharide (Step 2);

wherein

a starch debranching enzyme is also allowed to act in Step 1;

with the proviso that the method includes no step of allowing an exo-type amylase having actions of producing monosaccharides or disaccharides to act; and

the method comprises a step of hydrogenation after Step 1, but before the collection in Step 2.

15 . The saccharide composition according to claim 1 , further having the following characteristics (5) and (6):

(5) the saccharide composition comprises carbohydrate with a degree of polymerization of 1 or 2 at a total content of 16% by mass or lower, on a dry solid basis with respect to the total solid content; and

(6) the saccharide composition comprises carbohydrate with a degree of polymerization of 4 to 13 other than the cyclic tetrasaccharide and the branched cyclic tetrasaccharide comprising one or two glucose molecules linked to the cyclic tetrasaccharide, at a total content of over 37% by mass, on a dry solid basis with respect to the total solid content.

16 . A method of producing the saccharide composition according to claim 2 , comprising the steps of:

allowing α-isomaltosylglucosaccharide-forming enzyme and α-isomaltosyltransferase to act on a partial starch hydrolyzate, to produce the cyclic tetrasaccharide (Step 1); and

purifying and collecting the resulting enzyme reaction product containing the cyclic tetrasaccharide (Step 2);

wherein

a starch debranching enzyme is also allowed to act in Step 1;

with the proviso that the method includes no step of allowing an exo-type amylase having actions of producing monosaccharides or disaccharides to act.

17 . A method of producing the saccharide composition according to claim 3 , comprising the steps of:

allowing α-isomaltosylglucosaccharide-forming enzyme and α-isomaltosyltransferase to act on a partial starch hydrolyzate, to produce the cyclic tetrasaccharide (Step 1); and

purifying and collecting the resulting enzyme reaction product containing the cyclic tetrasaccharide (Step 2);

wherein

a starch debranching enzyme is also allowed to act in Step 1;

with the proviso that the method includes no step of allowing an exo-type amylase having actions of producing monosaccharides or disaccharides to act.

18 . A method of producing the saccharide composition according to claim 4 , comprising the steps of:

allowing α-isomaltosylglucosaccharide-forming enzyme and α-isomaltosyltransferase to act on a partial starch hydrolyzate, to produce the cyclic tetrasaccharide (Step 1); and

purifying and collecting the resulting enzyme reaction product containing the cyclic tetrasaccharide (Step 2);

wherein

a starch debranching enzyme is also allowed to act in Step 1;

with the proviso that the method includes no step of allowing an exo-type amylase having actions of producing monosaccharides or disaccharides to act.

19 . A method of producing the saccharide composition according to claim 5 , comprising the steps of:

allowing α-isomaltosylglucosaccharide-forming enzyme and α-isomaltosyltransferase to act on a partial starch hydrolyzate, to produce the cyclic tetrasaccharide (Step 1); and

purifying and collecting the resulting enzyme reaction product containing the cyclic tetrasaccharide (Step 2);

wherein

a starch debranching enzyme is also allowed to act in Step 1;

with the proviso that the method includes no step of allowing an exo-type amylase having actions of producing monosaccharides or disaccharides to act.

Assignments (2)
NUNC PRO TUNC ASSIGNMENT Recorded Sep 26, 2025
From: YASUDA, AKIKO; MIYATA, MANABU; YAMAMOTO, TAKUO; MIZOTE, AKIKO; MITSUZUMI, HITOSHI
To: HAYASHIBARA CO., LTD.
Reel/Frame 072389/0282 →
CHANGE OF NAME Recorded Nov 18, 2024
From: HAYASHIBARA CO., LTD
To: NAGASE VIITA CO., LTD.
Reel/Frame 069379/0708 →
Priority Claims (1)
JP 2019-183875 · Oct 4, 2019 · national
Continuity (1)
Related Publication 20230242957A1 · Aug 3, 2023
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