IP Library Granted Patent US 11,697,692
Granted Patent B2
US 11,697,692 · App. 16/761,115 · Granted Jul 11, 2023

Methods of producing glycan polymers

Inventors: John M. Geremia (Watertown, MA); Christopher Matthew Liu (Somerville, MA); Anastasia V. Lioubomirov (North Attleboro, MA)
Assignee: DSM Nutritional Products, LLC
C08B37/006
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Quick Facts
Patent No.
US 11,697,692
App. No.
16/761,115
Granted
Jul 11, 2023
Kind
B2
Abstract

Preparations of glycan polymers and variations thereof, pharmaceutical compositions, medical foods, supplements, foods, food ingredients, feed ingredients, and feed additives thereof, optionally comprising micronutrients, polyphenols, prebiotics, probiotics, or other agents are provided and methods of making same.

Claims (34)

1. A method of making a glycan polymer preparation having a mean degree of polymerization (DP) of at least 3 comprising:

A) providing a reaction mixture comprising:

i) one or more glycan units at an aqueous concentration of at least 0.30 kg/kg and

ii) an effective amount of an acid catalyst to form a glycosidic bond between two glycan units;

B) subjecting the reaction mixture of step A) to conditions that result in the evolution of H 2 O at a rate of at least 6 g of evolved H 2 O/kg input glycan/hour, wherein said conditions are achieved by controlling (a) the temperature or (b) pressure of the reaction mixture or both (a) and (b),

wherein the temperature is selected from between 100 and 160° C. at atmospheric pressure or equivalent temperature ranges at other pressures, and wherein the pressure is selected from between 0.01 and 30 psi, and quenching at least twice with water;

C) acquiring a value for a property of the glycan polymer preparation and further processing the glycan polymer preparation if a predetermined value of the property is met, wherein the property comprises a glycan polymer preparation property chosen from: degree of branching (DB), degree of polymerization (DP), alpha- to beta glycosidic bond ratio, number of distinct glycosidic bonds, glycosidic bond distribution, or final solubility limit in water of the glycan polymer preparation, and

D) responsive to the determination that the glycan polymer preparation meets the predetermined value for the property, formulating the glycan polymer preparation into a crystalline solid or powder and adding an excipient, anti-caking agent, or flowability agent to the glycan polymer preparation, thereby making a glycan polymer preparation with a mean DP of at least 3, wherein the mass of the glycan polymer preparation is at least 10 kg.

2. The method of claim 1 , comprising separating the glycan polymer preparation from the acid catalyst.

3. The method of claim 1 , further comprising:

acquiring a value for a second property of the glycan polymer preparation and further processing the glycan polymer preparation if a predetermined value of the property is met, wherein the second property is selected from:

the level of an impurity that alters the color or taste of the glycan polymer preparation, or

a release or quality control criterion chosen from: pH; microbial load; or heavy metal content, and

responsive to the determination that the glycan polymer preparation meets the predetermined value for the second property, performing one or more of:

dividing the glycan polymer preparation into a plurality of aliquots,

packaging the glycan polymer preparation, and

shipping the glycan polymer preparation to a different location.

4. The method of claim 3 , wherein the property comprises pH and-wherein pH of the glycan polymer preparation is from between about 2 to about 7.

5. The method of claim 3 , wherein the property comprises microbial load and wherein the glycan polymer preparation comprises less than 100 cfu/g yeast and mold.

6. The method of claim 3 , wherein the property comprises microbial load and wherein the glycan polymer preparation comprises an Aerobic Plate Count of less than 1000 cfu/g.

7. The method of claim 3 , wherein the property comprises heavy metal content, and wherein the glycan polymer preparation comprises i)<0.1 ppm Hg, ii)<0.1 ppm or <0.01 ppm As, iii)<0.1 ppm or <0.01 ppm Cd, iv)<0.1 ppm Pb, or any combination of i), ii), iii), and iv).

8. The method of claim 1 , wherein the glycan polymer preparation comprises at least two distinct glycan units.

9. The method of claim 1 , wherein the glycan polymer preparation comprises at least three distinct glycan units.

10. The method of claim 1 , wherein the glycan polymer preparation comprises 1, 2, 3, or all of:

i) glycosidic linkage distribution with a reference value of: 0-30 mol %-of 1,2-glycosidic bonds, 0-30 mol % of 1,3-glycosidic bonds, 0-50 mol % of 1,4-glycosidic bonds, and 0-80 mol % of 1,6-glycosidic bonds;

ii) average DP with a reference value of 5-20;

iii) alpha:beta ratio with a reference value of: 0.8:1 to 5:1; or

iv) degree of branching with a reference value of 0.05-0.5.

11. The method of claim 1 , wherein the reaction mixture does not comprise an active form of a glycosidic linkage modifying enzyme, or wherein at least 50% of the glycans in the glycan polymer preparation are synthesized under conditions which inactivate a glycosidic linkage modifying enzyme.

12. The method of claim 1 , wherein the one or more glycan units (i) consist of glucose, galactose, arabinose, xylose, mannose, fucose, fructose, or rhamnose; (ii) consist of two of glucose, galactose, mannose and arabinose; or (iii) consist of three of glucose, galactose, mannose and arabinose.

13. The method of claim 1 , wherein the glycan polymer preparation comprises at least 100 kg of glycans.

14. The method of claim 1 , wherein the glycan polymer preparation is suitable for pharmaceutical use, comprises a pharmaceutically acceptable excipient or solvent, or the glycan polymer preparation is pharmaceutical grade.

15. The method of claim 1 , wherein the glycan polymer preparation is suitable for use as a food, comprises another food or food ingredient, or wherein the glycan polymer preparation is food grade.

16. The method of claim 1 , wherein the glycan polymer preparation is suitable for consumption by animals or comprises another feed ingredient or carrier.

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE THE SECOND ASSIGNOR NAME PREVIOUSLY RECORDED AT REEL: 061404 FRAME: 0320. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Oct 18, 2022
From: KALEIDO BIOSCIENCES, INC.; CADENA BIO, INC.
To: HERCULES CAPITAL, INC.
Reel/Frame 061700/0414 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2022
From: HERCULES CAPITAL, INC.
To: DSM NUTRITIONAL PRODUCTS, LLC
Reel/Frame 061362/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 9, 2022
From: KALEIDO BIOSCIENCES, INC.; CARDENA BIO, INC.
To: HERCULES CAPITAL, INC.
Reel/Frame 061404/0320 →
Continuity (3)
Provisional Application 62581571 · Nov 3, 2017
Provisional Application 62720924 · Aug 21, 2018
Related Publication 20200354481A1 · Nov 12, 2020
Cited By (4)
US 12,410,206 US 12,508,274 US 12,514,267 US 12,661,366