Kojibiose

Kojibiose

Names
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
CAS Number	2140-29-6
3D model (Jmol)	Interactive image
ChEBI	CHEBI:33020
ChemSpider	144601
MeSH	Kojibiose
PubChem	164939
InChI 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 Key: PZDOWFGHCNHPQD-OQPGPFOOSA-N 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
SMILES 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
Chemical formula	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).
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Infobox references

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 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, an enzyme transforming sucrose and glucose into kojibiose has been developed, potentially solving the synthetization problem. ^[3]

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.
3. 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.