Crystal of 3'-sialyllactose sodium salt n-hydrate, and process for producing same

Patent metadata

Field	Value
Publication number	US-11008355-B2
Application number	US-201716099877-A
Country	US
Kind code	B2
Filing date	May 8, 2017
Priority date	May 9, 2016
Publication date	May 18, 2021
Grant date	May 18, 2021

Abstract

An object of the present invention is to provide a crystal of 3′-sialyllactose (hereinafter, referred to as 3SL), which is easily handled, and has high storage stability at normal temperature as well as under high temperature conditions, and provide a process for producing the same. The present invention relates to a 3SL sodium salt n-hydrate (wherein n represents any number of 0 to 9, and when n is 0, it is referred to as 3SL sodium salt anhydrate) and a process for producing the same.

First claim

The invention claimed is:

1. A crystal of 3′-sialyllactose (hereinafter, referred to as 3SL) sodium salt n-hydrate wherein n represents any number of 0 to 9, and when n is 0, it is referred to as 3SL sodium salt anhydrate,
wherein,
when n is any number of 4 to 9, the crystal has peaks at diffraction angles (2θ°) of 7.2±0.2°, 10.9±0.2°, 22.7±0.2°, 21.2±0.2°, and 9.8±0.2° in powder X-ray diffraction, and
when n is any number which is equal to or greater than 0 and less than 4, the crystal has peaks at diffraction angles (2θ°) of 8.9±0.2°, 17.1±0.2°, 15.5±0.2°, 19.3±0.2°, and 20.9±0.2° in powder X-ray diffraction.

2. The crystal according to claim 1 , wherein n is any number of 4 to 9.

3. The crystal according to claim 2 , wherein n is 5.0 or 8.0.

4. The crystal according to claim 2 , wherein the crystal further has peaks at diffraction angles (2θ°) of 23.3±0.2°, 21.8±0.2°, 17.1±0.2°, 17.8±0.2°, and 24.1±0.2° in powder X-ray diffraction.

5. The crystal according to claim 4 , wherein the crystal further has peaks at diffraction angles (2θ°) of 24.7±0.2°, 16.4±0.2°, 25.6±0.2°, 20.9±0.2°, and 23.9±0.2° in powder X-ray diffraction.

6. The crystal according to claim 2 , wherein the crystal has the following approximate cell parameters when measured at −173° C. in single crystal X-ray structure analysis: a=11.2942 A; b=13.3269 A; c=24.4525 A; V=3680.5 A 3 ; and Z=4, and has a space group of P2 1 2 1 2 1 .

7. The crystal according to claim 1 , wherein n is any number which is equal to or greater than 0 and less than 4.

8. The crystal according to claim 7 , wherein n is 1.4, 2.0, or 3.5.

9. The crystal according to claim 7 , wherein the crystal further has peaks at diffraction angles (2θ°) of 27.4±0.2°, 13.3±0.2°, 22.5±0.2°, 11.8±0.2°, and 23.7±0.2° in powder X-ray diffraction.

10. The crystal according to claim 9 , wherein the crystal further has peaks at diffraction angles (2θ°) of 25.0±0.2°, 10.8±0.2°, 17.9±0.2°, 20.0±0.2°, and 21.8±0.2° in powder X-ray diffraction.

11. A process for producing the crystal according to claim 2 , comprising a step of precipitating a crystal of 3SL sodium salt n-hydrate by causing a 3SL aqueous solution containing a sodium-containing compound to be left to stand or to be stirred, and a step of collecting the crystal of 3SL sodium salt n-hydrate from the aqueous solution.

12. A process for producing the crystal according to claim 2 , comprising a step of adding a crystal of 3SL sodium salt n-hydrate as a seed crystal to a 3SL aqueous solution containing a sodium-containing compound, a step of precipitating a crystal of 3SL sodium salt n-hydrate in the aqueous solution, and a step of collecting the crystal of 3SL sodium salt n-hydrate from the aqueous solution.

13. The process according to claim 12 , wherein the step of precipitating the crystal of 3SL sodium salt n-hydrate is a step of precipitating a crystal of 3SL sodium salt n-hydrate by adding or adding dropwise an alcohol solution to the aqueous solution.

14. The process according to claim 13 , wherein the alcohol solution is a solution selected from the group consisting of C1 to C6 alcohols.

15. A process for producing the crystal according to claim 7 , comprising a step of performing forced air drying of a crystal of 3′-sialyllactose sodium salt n-hydrate, wherein n is any number of 4 to 9, at 45° C. or more for 20 hours or more, or a step of performing vacuum drying of the same at 25° C. or more for 48 hours or more.

Assignees

• Kyowa Hakko Bio Co Ltd

Inventors

• Yokoi Tomoya
• Nagano Hiroshi
• MASE Kikue
• Abe Masahiro

Classifications

• C07H3/06 Primary

  Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• C07H1/00

  Processes for the preparation of sugar derivatives · CPC title

• C07H7/027 Primary

  Keto-aldonic acids · CPC title