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 (JSmol)	Interactive image;
ChEBI	CHEBI:33020 ;
ChemSpider	144601 ;
MeSH	Kojibiose
PubChem CID	164939;
UNII	9R6V2933TB ;
CompTox Dashboard (EPA)	DTXSID10943954 ;
	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 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]

References

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.
Siddiqua, I.R; Furgala, B (1967). "Isolation and characterization of oligosaccharides from honey". Journal of Apicultural Research. 6 (3): 139–145.
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.
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.

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[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] 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.