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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H22O11
Molecular Weight 342.2965
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GENTIOBIOSE

SMILES

OC[C@H]1O[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=AYRXSINWFIIFAE-UDKQPYHCSA-N
InChI=1S/C12H22O11/c13-1-4(15)7(17)8(18)5(16)3-22-12-11(21)10(20)9(19)6(2-14)23-12/h1,4-12,14-21H,2-3H2/t4-,5+,6+,7+,8+,9+,10-,11+,12+/m0/s1

HIDE SMILES / InChI

Molecular Formula C12H22O11
Molecular Weight 342.2965
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Gentiobiose is a rare disaccharide composed of two units of D-glucose joined with a beta (1->6) linkage. It occurs in living systems which use it both structurally and as energy source. Gentiobiose was first isolated from gentian roots and was shown to be involved in signaling pathways of the plant. Gentiobiose is incorporated into the chemical structure of crocin the chemical compound that gives saffron its color and that have shown potential anti-bacterial and anti-parasitic effects. Gentiobiose serves as a growth substrate and is a constituent of cell wall and deoxyribonucleic acid in microorganisms. Gentiobiose was found to be a specific substrate of β-glucosidase BglH from Aspergillus fungi which preferentially hydrolyzed gentiobiose rather than other oligosaccharides. Gentiobiose was used to study binding of V3-7Sh sIgM to zymosan while investigating a class of common pathogens as functional ligands for a subset of somatically mutated human B cell lymphomas. It was also used in binding assays to determine if coelomic cytolytic factor 1 (CCF-1) binds to β-1,3-glucans to stimulate the pro-PO-activating system.

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Binding of V3-7Sh sIgM to zymosan was studied using the flow cytometry analysis. Single colonies of bacteria and yeasts were isolated from agar plates and suspended in DMEM medium. 5 × 10^6 bacteria, 1.5 × 10^6 yeast, or ∼1 × 10^6 zymosan particles were stained with 2 µg/ml of sIgM and, subsequently, with anti-IgM F(ab′)2-PE. For inhibition experiments, ∼1 × 10^6 zymosan particles were stained in the presence of ≤10 µg/ml pustulan, mannan, or laminarin and ≤5 mM of gentiobiose. Competition by micromolar concentrations of gentiobiose inhibited binding to zymosan
Substance Class Chemical
Record UNII
HF30HB040V
Record Status Validated (UNII)
Record Version