Kojibiose

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Kojibiose
Kojibiose.png
Names
IUPAC name
2-O-α-D-Glucopyranosyl-D-glucose
Systematic IUPAC name
(2R,3S,4R,5R)-3,4,5,6-tetrahydroxy-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanal
Other names
2-alpha-D-glucosyl-D-glucose
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSH Kojibiose
PubChem CID
UNII
  • InChI=1S/C12H22O11/c13-1-4(16)7(17)8(18)5(2-14)22-12-11(21)10(20)9(19)6(3-15)23-12/h2,4-13,15-21H,1,3H2/t4-,5+,6-,7-,8-,9-,10+,11-,12+/m1/s1 Yes check.svgY
    Key: PZDOWFGHCNHPQD-OQPGPFOOSA-N Yes check.svgY
  • InChI=1/C12H22O11/c13-1-4(16)7(17)8(18)5(2-14)22-12-11(21)10(20)9(19)6(3-15)23-12/h2,4-13,15-21H,1,3H2/t4-,5+,6-,7-,8-,9-,10+,11-,12+/m1/s1
    Key: PZDOWFGHCNHPQD-OQPGPFOOBS
  • O=C[C@H](O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)[C@@H](O)[C@H](O)[C@H](O)CO
Properties
C12H22O11
Molar mass 342.30 g/mol
Density 1.688 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Kojibiose is a disaccharide. It is a product of the caramelization of glucose. [1] It is also present in honey (approx. 3%). [2]

Kojibiose has a mild sweet taste, but low calorie count. In combination with its prebiotic properties, kojibiose could function as a sugar substitute. However, kojibiose is hard to synthesize on an industrial scale. Recently, two enzyme approaches transforming sucrose and lactose or sucrose and glucose into kojibiose have been developed, potentially solving the synthetization problem. [3] [4]

Related Research Articles

<span class="mw-page-title-main">Disaccharide</span> Complex sugar

A disaccharide is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disaccharides are simple sugars soluble in water. Three common examples are sucrose, lactose, and maltose.

<span class="mw-page-title-main">Glucose</span> Naturally produced monosaccharide

Glucose is a sugar with the molecular formula C6H12O6. Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight, where it is used to make cellulose in cell walls, the most abundant carbohydrate in the world.

<span class="mw-page-title-main">Sugar</span> Sweet-tasting, water-soluble carbohydrates

Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose, fructose, and galactose. Compound sugars, also called disaccharides or double sugars, are molecules made of two bonded monosaccharides; common examples are sucrose, lactose, and maltose. White sugar is a refined form of sucrose. In the body, compound sugars are hydrolysed into simple sugars.

<span class="mw-page-title-main">Fructose</span> Simple ketonic monosaccharide found in many plants

Fructose, or fruit sugar, is a ketonic simple sugar found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. It is one of the three dietary monosaccharides, along with glucose and galactose, that are absorbed by the gut directly into the blood of the portal vein during digestion. The liver then converts both fructose and galactose into glucose, so that dissolved glucose, known as blood sugar, is the only monosaccharide present in circulating blood.

<span class="mw-page-title-main">Sucrose</span> Disaccharide made of glucose and fructose

Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula C
12
H
22
O
11
.

<span class="mw-page-title-main">Maltose</span> Chemical compound

Maltose, also known as maltobiose or malt sugar, is a disaccharide formed from two units of glucose joined with an α(1→4) bond. In the isomer isomaltose, the two glucose molecules are joined with an α(1→6) bond. Maltose is the two-unit member of the amylose homologous series, the key structural motif of starch. When beta-amylase breaks down starch, it removes two glucose units at a time, producing maltose. An example of this reaction is found in germinating seeds, which is why it was named after malt. Unlike sucrose, it is a reducing sugar.

<span class="mw-page-title-main">Inulin</span> Chemical compound

Inulins are a group of naturally occurring polysaccharides produced by many types of plants, industrially most often extracted from chicory. The inulins belong to a class of dietary fibers known as fructans. Inulin is used by some plants as a means of storing energy and is typically found in roots or rhizomes. Most plants that synthesize and store inulin do not store other forms of carbohydrate such as starch. In the United States in 2018, the Food and Drug Administration approved inulin as a dietary fiber ingredient used to improve the nutritional value of manufactured food products. Using inulin to measure kidney function is the "gold standard" for comparison with other means of estimating glomerular filtration rate.

<span class="mw-page-title-main">Inverted sugar syrup</span> Edible mixture of glucose and fructose, obtained from sucrose hydrolysis

Inverted sugar syrup, also called invert syrup, invert sugar, simple syrup, sugar syrup, sugar water, bar syrup, syrup USP, or sucrose inversion, is a syrup mixture of the monosaccharides glucose and fructose, that is made by hydrolytic saccharification of the disaccharide sucrose. This mixture's optical rotation is opposite to that of the original sugar, which is why it is called an invert sugar.

<span class="mw-page-title-main">Sugar alcohol</span> Organic compounds

Sugar alcohols are organic compounds, typically derived from sugars, containing one hydroxyl group (–OH) attached to each carbon atom. They are white, water-soluble solids that can occur naturally or be produced industrially by hydrogenating sugars. Since they contain multiple –OH groups, they are classified as polyols.

β-Fructofuranosidase is an enzyme that catalyzes the hydrolysis (breakdown) of the table sugar sucrose into fructose and glucose. Alternative names for β-fructofuranosidase EC 3.2.1.26 include invertase, saccharase, glucosucrase, β-fructosidase, invertin, sucrase, fructosylinvertase, alkaline invertase, acid invertase, and the systematic name: β-fructofuranosidase. The resulting mixture of fructose and glucose is called inverted sugar syrup. Related to invertases are sucrases. Invertases and sucrases hydrolyze sucrose to give the same mixture of glucose and fructose. Invertase is a glycoprotein that hydrolyses (cleaves) the non-reducing terminal β-fructofuranoside residues. Invertases cleave the O-C(fructose) bond, whereas the sucrases cleave the O-C(glucose) bond. Invertase cleaves the α-1,2-glycosidic bond of sucrose.

<span class="mw-page-title-main">Raffinose</span> Chemical compound

Raffinose is a trisaccharide composed of galactose, glucose, and fructose. It can be found in beans, cabbage, brussels sprouts, broccoli, asparagus, other vegetables, and whole grains. Raffinose can be hydrolyzed to D-galactose and sucrose by the enzyme α-galactosidase (α-GAL), an enzyme which in the lumen of the human digestive tract is only produced by bacteria in the large intestine. α-GAL also hydrolyzes other α-galactosides such as stachyose, verbascose, and galactinol, if present. The enzyme does not cleave β-linked galactose, as in lactose.

<span class="mw-page-title-main">High-fructose corn syrup</span> Processed corn syrup

High-fructose corn syrup (HFCS), also known as glucose–fructose, isoglucose and glucose–fructose syrup, is a sweetener made from corn starch. As in the production of conventional corn syrup, the starch is broken down into glucose by enzymes. To make HFCS, the corn syrup is further processed by D-xylose isomerase to convert some of its glucose into fructose. HFCS was first marketed in the early 1970s by the Clinton Corn Processing Company, together with the Japanese Agency of Industrial Science and Technology, where the enzyme was discovered in 1965.

Disaccharidases are glycoside hydrolases, enzymes that break down certain types of sugars called disaccharides into simpler sugars called monosaccharides. In the human body, disaccharidases are made mostly in an area of the small intestine's wall called the brush border, making them members of the group of "brush border enzymes".

<span class="mw-page-title-main">Fructan</span> Fructose polymer

A fructan is a polymer of fructose molecules. Fructans with a short chain length are known as fructooligosaccharides. Fructans can be found in over 12% of the angiosperms including both monocots and dicots such as agave, artichokes, asparagus, leeks, garlic, onions, yacón, jícama, barley and wheat.

<span class="mw-page-title-main">Isomaltulose</span> Chemical compound

Isomaltulose is a disaccharide carbohydrate composed of glucose and fructose. It is naturally present in honey and sugarcane extracts and is also produced industrially from table sugar (sucrose) and used as a sugar alternative.

<span class="mw-page-title-main">Nigerose</span> Chemical compound

Nigerose, also known as sakebiose, is an unfermentable sugar obtained by partial hydrolysis of nigeran, a polysaccharide found in black mold, but is also readily extracted from the dextrans found in rice molds and many other fermenting microorganisms, such as L. mesenteroides. It is a disaccharide made of two glucose residues, connected with a 1->3 link. It is a product of the caramelization of glucose.

Isomaltooligosaccharide (IMO) is a mixture of short-chain carbohydrates which has a digestion-resistant property. IMO is found naturally in some foods, as well as being manufactured commercially. The raw material used for manufacturing IMO is starch, which is enzymatically converted into a mixture of isomaltooligosaccharides.

<span class="mw-page-title-main">Added sugar</span> Caloric sweeteners added to food and beverages

Added sugars or free sugars are sugar carbohydrates added to food and beverages at some point before their consumption. These include added carbohydrates, and more broadly, sugars naturally present in honey, syrup, and fruits. They can take multiple chemical forms, including sucrose, glucose (dextrose), and fructose.

<span class="mw-page-title-main">Kestose</span> Sugar from fructooligosaccharide group

Kestose is a class of sugars that belongs to a group of fructooligosaccharides.

References

  1. Sugisawa, Hirqshi; Edo, Hiroshi (1966). "The Thermal Degradation of Sugars I. Thermal Polymerization of Glucose". Journal of Food Science. 31 (4): 561. doi:10.1111/j.1365-2621.1966.tb01905.x.
  2. Siddiqua, I.R; Furgala, B (1967). "Isolation and characterization of oligosaccharides from honey". Journal of Apicultural Research. 6 (3): 139–145. doi:10.1080/00218839.1967.11100174.
  3. Diez-Municio, Marina; Montilla, Antonia; Moreno, F. Javier; Herrero, Miguel (2014). "A sustainable biotechnological process for the efficient synthesis of kojibiose". Green Chemistry. 16 (4): 2219–2226. doi:10.1039/C3GC42246A. hdl: 10261/99797 .
  4. Verhaeghe, Tom; De Winter, Karel (2016). "Converting bulk sugars into prebiotics: semi-rational design of a transglucosylase with controlled selectivity". Chemical Communications. 52 (18): 2687–3689. doi:10.1039/C5CC09940D. PMID   26858011.