Nigerose

Nigerose^[1]

Names
IUPAC name (2R,3S,4S,5R,6R)-2-(Hydroxymethyl)-6-[(3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl]oxyoxane-3,4,5-triol
Other names 3-O-α-D-glucopyranosyl-D-glucose
Identifiers
CAS Number	497-48-3
3D model (Jmol)	Interactive image
ChemSpider	388607
MeSH	Nigerose
PubChem	439512
InChI InChI=1S/C12H22O11/c13-1-3-5(15)7(17)8(18)12(22-3)23-10-6(16)4(2-14)21-11(20)9(10)19/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8-,9-,10+,11?,12-/m1/s1 Key: QIGJYVCQYDKYDW-NSYYTRPSSA-N InChI=1/C12H22O11/c13-1-3-5(15)7(17)8(18)12(22-3)23-10-6(16)4(2-14)21-11(20)9(10)19/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8-,9-,10+,11?,12-/m1/s1 Key: QIGJYVCQYDKYDW-NSYYTRPSBG
SMILES O([C@H]1[C@H](O)[C@H](OC(O)[C@@H]1O)CO)[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO
Properties
Chemical formula	C12H22O11
Molar mass	342.29648
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

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,^[2] such as L. mesenteroides.^[3] It is a disaccharide made of two glucose residues, connected with a 1->3 link. It is a product of the caramelization of glucose.^[4]

References

1. Nigerose - Compound Summary, PubChem.
2. Matsuda, Kazuo; H. Wanatabe; K. Fujimoto; K. Aso (1961). "Isolation of Nigerose and Kojibiose from Dextrans". Nature. 191 (4785): 278. doi:10.1038/191278a0. PMID 13768213.
3. Matsuda, Kazuo; Hiroshi Watanabe; Kiyoshi Aso (1962-03-10). "Acetolysis of polysaccharides I. Isolation of nigerose from the acetolysate of a dextran produced by Leuconostoc mesenteroides NRRL B-421". Tohoku journal of agricultural research. Faculty of Agriculture, Tohoku University. 12 (4): 351–357. Retrieved 2008-11-21.
4. 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.