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51555-87-4,MFCD00057491
Catalog No.:AA00DCTP

51555-87-4 | (2R,3R,4S,5R)-2-(hydroxymethyl)-6-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}oxane-3,4,5-triol

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25mg
≥98%
in stock  
$63.00   $44.00
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50mg
≥98%
in stock  
$120.00   $84.00
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100mg
≥98%
in stock  
$172.00   $120.00
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250mg
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$246.00   $172.00
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1g
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00DCTP
Chemical Name:
(2R,3R,4S,5R)-2-(hydroxymethyl)-6-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}oxane-3,4,5-triol
CAS Number:
51555-87-4
Molecular Formula:
C12H22O10S
Molecular Weight:
358.3621
MDL Number:
MFCD00057491
SMILES:
OC[C@H]1O[C@@H](S[C@@H]2O[C@H](CO)[C@@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@H]1O)O)O
Properties
Properties
 
Form:
Solid  
MP:
>225°C (dec.)  
Storage:
Keep in dry area;-20 ℃;Inert atmosphere;  

Computed Properties
 
Complexity:
353  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
11  
Hydrogen Bond Donor Count:
8  
Rotatable Bond Count:
4  
Undefined Atom Stereocenter Count:
1  
XLogP3:
-3.4  

Literature

Title: Thiodigalactoside inhibits murine cancers by concurrently blocking effects of galectin-1 on immune dysregulation, angiogenesis and protection against oxidative stress.

Journal: Angiogenesis 20110901

Title: Symmetric dithiodigalactoside: strategic combination of binding studies and detection of selectivity between a plant toxin and human lectins.

Journal: Organic & biomolecular chemistry 20110807

Title: 1H-1,2,3-triazol-1-yl thiodigalactoside derivatives as high affinity galectin-3 inhibitors.

Journal: Bioorganic & medicinal chemistry 20100715

Title: Effect of recombinant galectin-1 on the growth of immortal rat chondrocyte on chitosan-coated PLGA scaffold.

Journal: Journal of biomedical materials research. Part A 20100615

Title: Synthesis and evaluation of new thiodigalactoside-based chemical probes to label galectin-3.

Journal: Chembiochem : a European journal of chemical biology 20090706

Title: Galectin-inhibitory thiodigalactoside ester derivatives have antimigratory effects in cultured lung and prostate cancer cells.

Journal: Journal of medicinal chemistry 20081225

Title: The Cys154-->Gly mutation in LacY causes constitutive opening of the hydrophilic periplasmic pathway.

Journal: Journal of molecular biology 20080613

Title: Galectin-8 induces apoptosis in the CD4(high)CD8(high) thymocyte subpopulation.

Journal: Glycobiology 20071201

Title: Conformational change in an MFS protein: MD simulations of LacY.

Journal: Structure (London, England : 1993) 20070701

Title: Galectin-8 binds specific beta1 integrins and induces polarized spreading highlighted by asymmetric lamellipodia in Jurkat T cells.

Journal: Experimental cell research 20060215

Title: Coexpression, purification and characterization of the E and S subunits of coenzyme B(12) and B(6) dependent Clostridium sticklandii D-ornithine aminomutase in Escherichia coli.

Journal: European journal of biochemistry 20041101

Title: X-ray crystal structure of a galactose-specific C-type lectin possessing a novel decameric quaternary structure.

Journal: Biochemistry 20040406

Title: Structure and mechanism of the lactose permease of Escherichia coli.

Journal: Science (New York, N.Y.) 20030801

Title: Aromatic stacking in the sugar binding site of the lactose permease.

Journal: Biochemistry 20030218

Title: Manipulating conformational equilibria in the lactose permease of Escherichia coli.

Journal: Journal of molecular biology 20020125

Title: Helix packing in the lactose permease of Escherichia coli: localization of helix VI.

Journal: Journal of molecular biology 20010907

Title: A triple mutant, K319N/H322Q/E325Q, of the lactose permease cotransports H+ with thiodigalactoside.

Journal: The Journal of membrane biology 20010601

Title: Developing a dynamic pharmacophore model for HIV-1 integrase.

Journal: Journal of medicinal chemistry 20000601

Title: Hilde van Hattum, et al. Tuning the Preference of Thiodigalactoside- And Lactosamine-Based Ligands to galectin-3 Over galectin-1. J Med Chem. 2013 Feb 14;56(3):1350-4.

Title: Varun V Prabhu, et al. Small-Molecule ONC201/TIC10 Targets Chemotherapy-Resistant Colorectal Cancer Stem-like Cells in an Akt/Foxo3a/TRAIL-Dependent Manner. Cancer Res. 2015 Apr 1;75(7):1423-32.

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Tags:51555-87-4 Molecular Formula|51555-87-4 MDL|51555-87-4 SMILES|51555-87-4 (2R,3R,4S,5R)-2-(hydroxymethyl)-6-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}oxane-3,4,5-triol