EP-3166981-B1 - OLIGOSACCHARIDE COMPOSITIONS AND METHODS FOR PRODUCING THEREOF

Inventors

• GEREMIA, John, M.
• MURPHY, Anastasia, V.
• HAN, SCOTT
• SEIGAL, Benjamin, A.
• LANDRY, Alicia
• SHERRY, Kyle
• PANOS, Stephen
• CHURCHMAN, Devin
• O'CONNOR, ANDREW

Dates

Publication Date

20260513

Application Date

20150709

Claims (11)

1. An oligosaccharide composition comprising one or more oligosaccharides, wherein the one or more oligosaccharide comprises monosaccharide monomers linked by glycosidic bonds, wherein the monosaccharide monomers are independently selected from the group consisting of C5 monosaccharides and C6 monosaccharides, each glycosidic bond is independently selected from the group consisting of α-1 ,4-bonds, α-1,2-bonds, β-1,2-bonds, α-1,3-bonds, β-1,3-bonds, β-1,4-bonds, α-1,6-bonds, and β-1-,6 bonds, wherein at least a portion of the oligosaccharide composition comprises at least two different glycosidic linkages, wherein greater than 50% of the one or more oligosaccharides is a dietary fiber, and wherein the dietary fiber is a carbohydrate with a degree of polymerization of at least 3 that is not effectively hydrolyzed to its constituent sugars in humans or animals by enzymes in the stomach or small intestine; wherein the oligosaccharide composition has a mean degree of polymerization (DP) of 5-10, a glass transition temperature (Tg) of >50, and a hygroscopicity of >5%, wherein the mean DP is determined as the number average of species containing one, two, three, four, five, six, seven, eight, nine, ten to fifteen, and greater than fifteen, anhydrosugar monomer units, wherein the Tg is determined by differential scanning calorimetry, and wherein the hygroscopicity is determined by measuring the mass gain of the composition after equilibration in a fixed water activity atmosphere; and wherein the oligosaccharide composition is produced by combining one or more sugars with a catalyst, wherein the catalyst is a polymeric catalyst comprising acidic monomers and ionic monomers.
2. The oligosaccharide composition of claim 1, wherein the monosaccharide monomers are independently selected from the group consisting of glucose, galactose, xylose, arabinose, fructose, mannose, ribose, allose, fucose, glyceraldehyde and rhamnose.
3. The oligosaccharide composition according to any one of claims 1 or 2, wherein the monosaccharide monomers connected by glycosidic bonds form oligomer backbones, and wherein at least a portion of the oligosaccharide composition further comprises one or more bridging functional groups, wherein: each bridging functional group independently connects one of the oligomer backbones to an additional monosaccharide monomer, a disaccharide, or an additional oligomer backbone; and the one or more bridging functional groups are independently selected from the group consisting of polyols, polycarboxylic acids and amino acids.
4. The oligosaccharide composition of claim 3, wherein the monosaccharide monomers connected by glycosidic bonds form oligomer backbones, and wherein each additional oligomer backbone is independently substituted with one or more pendant functional groups independently selected from the group consisting of carboxylic acids, sugar alcohols, amino acids, amino sugars, alcohols, sulfate and phosphate.
5. The oligosaccharide composition of claim 4, wherein the one or more pendant functional groups are independently selected from the group consisting of glucosamine, galactosamine, citric acid, succinic acid, glutamic acid, aspartic acid, glucuronic acid, butyric acid, itaconic acid, malic acid, maleic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, adipic acid, isobutyric acid, formic acid, levulinic acid, valeric acid, isovaleric acid, sorbitol, xylitol, arabitol, glycerol, erythritol, mannitol, galacitol, fucitol, iditol, inositol, volemitol, lacitol, ethanol, propanol, butanol, pentanol, hexanol, propanediol, butanediol, pentanediol, sulfate and phosphate.
6. The oligosaccharide composition of any one of claims 3 to 5, wherein the one or more bridging functional groups are independently selected from the group consisting of glucosamine, galactosamine, lactic acid, acetic acid, citric acid, pyruvic acid, succinic acid, glutamic acid, aspartic acid, glucuronic acid, itaconic acid, malic acid, maleic acid, adipic acid, sorbitol, xylitol, arabitol, glycerol, erythritol, mannitol, galacitol, fucitol, iditol, inositol, volemitol, lacitol, propanediol, butanediol, pentanediol, sulfate and phosphate.
7. The oligosaccharide composition of any of claims 1 to 6, wherein at least 10% of the one or more oligosaccharides comprised in the oligosaccharide composition has a number average molecular weight between 230 to 10,000 g/mol.
8. The oligosaccharide composition according to any one of claims 1 to 7, wherein the dietary fiber content of the oligosaccharide composition is at least 80% on a dry mass basis.
9. The oligosaccharide composition according to any one of claims 1 to 8, wherein the oligosaccharide composition comprises dietary fiber that is soluble in water to a maximum concentration of at least 50 Brix.
10. The oligosaccharide composition according to any one of claims 1 to 9, wherein the dietary fiber content of the one or more oligosaccharides can be determined by the in vitro method AOAC 2009.01 to quantify the fraction of oligosaccharides in the composition that have a degree of polymerization (DP) of at least three and that are not hydrolyzed by a combination of the enzymes α-amylase, amyloglucosidase and protease.
11. The oligosaccharide composition according to any one of claims 1-10, wherein the one or more sugars is one or more C5 or C6 monosaccharides.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority to U.S. Provisional Patent Application Nos. 62/022,579 filed July 9, 2014, and 62/108,035 filed January 26, 2015. FIELD The present disclosure relates generally to oligosaccharide compositions and methods of producing such oligosaccharide compositions, and more specifically to methods of using catalysts having acidic and ionic groups to polymerize sugars, such as glucose and galactose, to produce oligosaccharide compositions. BACKGROUND The condensation of sugars to soluble oligosaccharides is of great economic, nutritional, and therapeutic relevance. It is well known that the consumption of excess sugar by humans and animals has been linked to a variety of negative health indications, such as obesity and diabetes. It is further established that diets rich in fiber, such as indigestible oligosaccharides and polysaccharides, promote health and well being. Some dietary fibers interact favorably with the ecosystem of human and animal gut micro biota, stimulating the growth of advantageous gut bacteria, inhibiting the growth of undesirable gut bacteria, and inhibiting the ability of pathogenic bacteria to colonize the gut. Oligosaccharides can be added to foods to empart favorable flavor, mouth feel, and consistency. Furthermore, oligosaccharides that are not digestible by humans contribute little or no caloric value to foods. There is significant commercial interest in replacing some portion of the raw sugar ingredients in foods with oligosaccharides to reduce the caloric content of those foods and improve their impact on the human microbiome. There is interest in incorporating oligosaccharide ingredients to reduce the sugar content and enhace the dietary fiber content of breakfast cereals, granola and other type of bars, yogurt, ice cream, breads, cake mixes, and nutritional shakes and supplements. There is additional interest in incorporating oligosaccharide ingredients into animal feed to improve its nutritional quality. Oligosaccharides can be added to animal feed to improve gut health, increase weight gain, and promote feed efficiency. Furthermore, oligosaccharides that are not digestible by animals pass through the stomach and upper digestive system and can be feremented by gut micro-organisms. There is commercial interest in incorporating oligosaccharides into poultry, swine, aquaculture, and ruminant diets to improve the animal microbiome. To achieve objectives pertaining to improved human and animal nutrition and health, oligosaccharides with a particular structure or range of structural properties are desired. At present, however, such oligosaccharides are limited to those obtained from sources such as corn meal, yeast bodies, dairy products, inulin, gums (such as guar gum or acacia gum), pectins, hemicellulose extracts, and other such agricultural and industrial food products. In other cases, oligosaccharides are produced by fermentation, roasting of starches and grains, and by polymerizing glucose in the presence of aqueous acids. The types of oligosaccharides obtained by biological production are limited in the variety of chemical structures that can be produced, the high cost of industrial fermentations, and the complex purification processes required to remove salts, buffers, and other fermentation byproducts to render the oligosaccharides suitable for human consumption. Methods known in the art are limited in the variety of oligosaccharide structures that can be produced, and often have additional costly production steps. These can include neutralizing and/or removing aqueous acids or their salts, de-colorizing the product to a suitable level, and isolation and disposal of used catalyst that cannot be recycled. US 2013/0216693 relates to a process for making an oligosaccharide composition. US 6,677,142 relates to a method for producing polysaccharides containing α-1-4-glucan chains. US 5,580,762 relates to a method of producing an oligosaccharide of a higher polymerization degree. US 2014/0060522 relates to catalysts useful in non-enzymatic saccharification processes. US 2012/020740 relates to polymers useful as catalysts in non-enzymatic saccharification processes. Roberfroid and Slavin, Critical Reviews in Food Science and Nutrition, 40(6):461-480 (2000), is a review relating to nondigestible oligosaccharides. Mussatto and Mancilha, Carbohydrate Polymers 68:587-597 (2007), is a review relating to non-digestible oligosaccharides. Chapter 1 of Food Carbohydrates: Chemistry, Physical Properties and Applications, edited by Steve W. Cui, published in 2005 by CRC Press, Tayler & Francis Group, ISBN 0-8493-1574-3 relates to basic chemistry of food carbohydrates. As such, there is an ongoing need for improved methods of producing oligosaccharides on a commercially-viable scale. BRIEF SUMMARY The present disclosure addresses this need by providing methods of producing oligosaccharide compositions and functionalized oligosaccharid