Laminaribiose

Laminaribiose
Names
	IUPAC name 3-β-D-Glucopyranosyl-(1→3)-D-glucose
	Systematic IUPAC name (2R,3S,4R,5R)-2,4,5,6-Tetrahydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexanal
	Other names 3-β-D-Glucosyl-D-glucose
Identifiers
CAS Number	34980-39-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	388710 ;
PubChem CID	439637;
UNII	0WN3D69UW4 ;
	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-LCOYTZNXSA-N ;
	SMILES O([C@H]1[C@H](O)[C@H](OC(O)[C@@H]1O)CO)[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O;
Properties
Chemical formula	C12H22O11
Molar mass	342.30 g/mol
Density	1.768 g/mL
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Laminaribiose C₁₂H₂₂O₁₁ is a disaccharide which is used notably in the agricultural field and as an antiseptic. It is in general obtained by hydrolysis or by acetolysis of natural polysaccharides of plant origin.^[1] It is also a product of the caramelization of glucose.^[2]

Biosynthesis

In some plants, the enzyme laminaribiose phosphorylase catalyzes a reversible chemical reaction that produces laminaribiose from α-D-glucose 1-phosphate and D-glucose:

2D representation of the chemical structure of Q418865.

α-D-glucose 1-phosphate

+

2D representation of the chemical structure of Q23905964.

D-glucose

P_i

Reversible left-right reaction arrow with minor forward product(s) to top right and minor reverse substrate(s) from bottom right

P_i

laminaribiose

The enzyme has been found in Euglena gracilis and Astasia ocellata.^[3]^[4]

References

↑ US 6632940
↑ 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.
↑ Goldemberg SH, Marechal LR, De Souza BC (1966). "Beta-1,3-oligoglucan: orthophosphate glucosyltransferase from Euglena gracilis". Journal of Biological Chemistry. 241 (1): 45–50. doi:10.1016/S0021-9258(18)96955-3. PMID 5901055.
↑ Manners DJ, Taylor DC (1967). "Studies on carbohydrate metabolizing enzymes. XVI. Specificity of laminaribiose phosphorylase from Astasia ocellata". Archives of Biochemistry and Biophysics. 121 (2): 443–51. doi:10.1016/0003-9861(67)90099-9. PMID 6057111.

[1] US 6632940

[2] 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.

[3] Goldemberg SH, Marechal LR, De Souza BC (1966). "Beta-1,3-oligoglucan: orthophosphate glucosyltransferase from Euglena gracilis". Journal of Biological Chemistry. 241 (1): 45–50. doi:10.1016/S0021-9258(18)96955-3. PMID 5901055.

[4] Manners DJ, Taylor DC (1967). "Studies on carbohydrate metabolizing enzymes. XVI. Specificity of laminaribiose phosphorylase from Astasia ocellata". Archives of Biochemistry and Biophysics. 121 (2): 443–51. doi:10.1016/0003-9861(67)90099-9. PMID 6057111.

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