D-Galactopyranosyl-β-D-thiogalactopyranoside - ≥98% , CAS No.51555-87-4

CAS: 51555-87-4 Cat. No.: D343351 Molecular Weight: 358.36

GRADE & PURITY ≥98%

Synonyms

(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyloxane-3,4,5-triol | Thiodigalactoside | Tdg cpd | D-Galactopyranosylthio-β-D-galactopyranoside | β-D-Galactopyranosyl 1-thio-β-D-galactopyranoside |

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

D-Galactopyranosyl-β- D-thiogalactopyranoside (Thiodigalactoside) is a compound belonging to the dihexoses (disaccharides containing two hexose carbohydrates). Thiodigalactoside is known to target galectin-1, heat-labile enterotoxin b chain, neurocan core protein, and lactose permease.|D-Galactopyranosyl-β- D-thiogalactopyranoside is often used to study galectins, a family of glycan-binding lectins with diverse regulatory roles in physiological processes. Galectins have significant roles in inflammation and cancer. Thiodigalactoside is a diglycan that binds galectins-1, -3, -8, and -9 with Kd values between 24 and 78 μM. It is used to investigate the roles of these galectins in cell signaling and carcinogenesis.

Specifications

Synonyms

(2R, 3R, 4S, 5R, 6S)-2-(hydroxymethyl)-6-[(2S, 3R, 4S, 5R, 6R)-3, 4, 5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyloxane-3, 4, 5-triol | Thiodigalactoside | Tdg cpd | D-Galactopyranosylthio-β-D-galactopyranoside | β-D-Galactopyranosyl 1-thio-β-D-galactopyranoside |

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Thiodigalactoside (TDG)is a potent inhibitor of galectin-1 (GAL1) that suppress tumor growth by inhibiting multiple cancer enhancing activities of galectin-1, including immune cell dysregulation, angiogenesis and protection against oxidative stress. Thiod

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Purity

≥98%

Product Properties

• pKa: pKₐ: 12.63 (Predicted)

Names and Identifiers

• Pubchem Sid: 504756806
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504756806
• Canonical Smiles: C(C1C(C(C(C(O1)SC2C(C(C(C(O2)CO)O)O)O)O)O)O)O
• IUPAC Name: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyloxane-3,4,5-triol
• InChIKey: SYKYBMOFPMXDRQ-ZFDCCPEWSA-N
• INCHI: 1S/C12H22O10S/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2/t3-,4-,5+,6+,7+,8+,9-,10-,11+,12+/m1/s1
• Isomeric SMILES: C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)S[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)O)O)O)O
• Molecular Weight: 358.36
• Reaxy-Rn: 11730146
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=11730146&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 Thioglycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: Thioglycosides
• Alternative Parents: Thio-linked disaccharides Oxanes Monothioacetals Secondary alcohols Sulfenyl compounds Polyols Oxacyclic compounds Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Thio-linked disaccharide - S-glycosyl compound - Disaccharide - Oxane - Monothioacetal - Secondary alcohol - Oxacycle - Organoheterocyclic compound - Sulfenyl compound - Polyol - Hydrocarbon derivative - Primary alcohol - Organosulfur compound - Alcohol - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as thioglycosides. These are glycoside in which a sugar group is bonded through one carbon to another group via a S-glycosidic bond.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

LGALS1 Tchem Galectin-1 (387 Activities)

Discover Target: LGALS1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LGALS9 Tchem Galectin-9 (186 Activities)

Discover Target: LGALS9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LGALS8 Tchem Galectin-8 (303 Activities)

Discover Target: LGALS8

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LGALS7 Tbio Galectin-7 (120 Activities)

Discover Target: LGALS7

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LGALS2 Tbio Galectin-2 (56 Activities)

Discover Target: LGALS2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Lgals3 Galectin-3 (98 Activities)

Discover Target: Lgals3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: ≥35.8 mg/mL in H2O; insoluble in EtOH; ≥52.5 mg/mL in DMSO
• Refractive Index: n20D~1.69 (Predicted)
• Boil Point(°C): ~712.6° C at 760 mmHg (Predicted)
• Melt Point(°C): 229-235° C
• Molecular Weight: 358.360 g/mol
• XLogP3: -3.400
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 358.093 Da
• Monoisotopic Mass: 358.093 Da
• Topological Polar Surface Area: 206.000 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 353.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1