Kojibiose

Kojibiose
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
CAS Number
  • 2140-29-6 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:33020 checkY
ChemSpider
  • 144601 checkY
MeSH Kojibiose
PubChem CID
  • 164939
UNII
  • 9R6V2933TB checkY
CompTox Dashboard (EPA)
  • DTXSID10943954 Edit this at Wikidata
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 checkY
    Key: PZDOWFGHCNHPQD-OQPGPFOOSA-N checkY
  • 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
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
Chemical compound

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

  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.
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