42891-22-5

Basic information

• Product Name: 1-THIO-BETA-D-GALACTOPYRANOSE SODIUM SALT
• Synonyms: THIO-BETA-D-GALACTOPYRANOSE SODIUM SALT;1-THIO-B-D-GALACTOSE, SODIUM SALT;1-THIO-BETA-D-GALACTOPYRANOSE SODIUM SALT;1-THIO-BETA-D-GALACTOSE SODIUM SALT;1-thio-B-D-galactopyranose sodium;.beta.-D-Galactopyranose, 1-thio-, monosodium salt;b-D-Thiogalactosesodiumsalt;1-THIO-SS-D-GALACTOPYRANOSE SODIUM SALT
• CAS NO: 42891-22-5
• Molecular Formula: C₆H₁₁O₅S*Na
• Molecular Weight: 218.2
• Product Categories: Carbohydrates & Derivatives;Carbohydrates
• Mol File: 42891-22-5.mol

Chemical Properties

• Melting Point: 145-150°C dec.
• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Water
• CAS DataBase Reference: 1-THIO-BETA-D-GALACTOPYRANOSE SODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: 1-THIO-BETA-D-GALACTOPYRANOSE SODIUM SALT(42891-22-5)
• EPA Substance Registry System: 1-THIO-BETA-D-GALACTOPYRANOSE SODIUM SALT(42891-22-5)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 42891-22-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-Thio-beta-D-Galactopyranose sodium salt is used as a synthetic building block for the creation of various complex organic molecules. Its unique chemical properties allow it to be a versatile component in the synthesis of a wide range of compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-Thio-beta-D-Galactopyranose sodium salt is used as a key intermediate in the development of novel therapeutic agents. Its ability to form specific interactions with biological targets makes it a valuable component in the design and synthesis of new drugs, particularly those targeting carbohydrate-binding proteins and enzymes.
Used in Research and Development:
1-Thio-beta-D-Galactopyranose sodium salt is also employed in research and development settings, where it serves as a valuable tool for studying the structure, function, and interactions of carbohydrates and their derivatives. It can be used to investigate the role of carbohydrates in various biological processes, such as cell signaling, immune response, and molecular recognition.
Used in Material Science:
In the field of material science, 1-Thio-beta-D-Galactopyranose sodium salt can be utilized in the development of advanced materials with specific properties, such as improved biocompatibility, enhanced stability, or targeted drug delivery capabilities. Its unique chemical structure allows it to be incorporated into various material systems, including polymers, nanoparticles, and hydrogels.

InChI:InChI=1/C6H12O5S.Na/c7-1-2-3(8)4(9)5(10)6(12)11-2;/h2-10,12H,1H2;/q;+1/p-1/t2?,3-,4?,5?,6-;/m0./s1/rC6H11NaO5S/c7-13-6-5(11)4(10)3(9)2(1-8)12-6/h2-6,8-11H,1H2/t2?,3-,4?,5?,6-/m0/s1

Upstream product

• 6806-56-0 2,3,4,6-tetra-O-acetyl-1S-acetyl-1-thio-β-D-galactopyranose 
• 19879-84-6 2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 

Downstream Products

• 398469-82-4 1,3-bis(5-thio-β-D-galactopyranosyldisulfanylmethyl)-5-methanethiosulfonatomethyl-2,4,6-trimethylbenzene 
• 398469-83-5 1,3-bis(methanethiosulfonatomethyl)-5-thio-β-D-galactopyranosyldisulfanylmethyl-2,4,6-trimethyl-benzene 
• 398469-84-6 tris-(thio-β-D-galactopyranosyldisulfanylmethyl)-mesitylene 

Relevant articles and documents

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

Thioglycosides offer the advantage over O-glycosides to be resistant to hydrolysis. Based on initial evidence of this recognition ability for glycosyldisulfides by screening dynamic combinatorial libraries, we have now systematically studied dithiodigalactoside on a plant toxin (Viscum album agglutinin) and five human lectins (adhesion/growth-regulatory galectins with medical relevance e.g. in tumor progression and spread). Inhibition assays with surface-presented neoglycoprotein and in solution monitored by saturation transfer difference NMR spectroscopy, flanked by epitope mapping, as well as isothermal titration calorimetry revealed binding properties to VAA (K a: 1560 ± 20 M-1). They were reflected by the structural model and the affinity on the level of toxin-exposed cells. In comparison, galectins were considerably less reactive, with intrafamily grading down to very minor reactivity for tandem-repeat-type galectins, as quantitated by radioassays for both domains of galectin-4. Model building indicated contact formation to be restricted to only one galactose moiety, in contrast to thiodigalactoside. The tested glycosyldisulfide exhibits selectivity between the plant toxin and the tested human lectins, and also between these proteins. Therefore, glycosyldisulfides have potential as chemical platform for inhibitor design.

Synthesis and Structure-Activity Relationship Study of Antimicrobial Auranofin against ESKAPE Pathogens

Auranofin, an FDA-approved arthritis drug, has recently been repurposed as a potential antimicrobial agent; it performed well against many Gram-positive bacteria, including multidrug resistant strains. It is, however, inactive toward Gram-negative bacteria, for which we are in dire need of new therapies. In this work, 40 auranofin analogues were synthesized by varying the structures of the thiol and phosphine ligands, and their activities were tested against ESKAPE pathogens. The study identified compounds that exhibited bacterial inhibition (MIC) and killing (MBC) activities up to 65 folds higher than that of auranofin, making them effective against Gram-negative pathogens. Both thiol and the phosphine structures influence the activities of the analogues. The trimethylphosphine and triethylphosphine ligands gave the highest activities against Gram-negative and Gram-positive bacteria, respectively. Our SAR study revealed that the thiol ligand is also very important, the structure of which can modulate the activities of the AuI complexes for both Gram-negative and Gram-positive bacteria. Moreover, these analogues had mammalian cell toxicities either similar to or lower than that of auranofin.

SYNTHESIS AND USE OF GLYCODENDRIMER REAGENTS

The present invention relates to a chemically modified mutant protein including a cysteine residue substituted for a residue other than cysteine n a precursor protein, the substituted cysteine residue being subsequently modified by reacting the cysteine residue with a glycosylated thiosulfonate. Also a method of producing the chemically modified mutant protein is provided. The present invention also relates to a glycosylated methanethiosulfonate. Another aspect of the present invention is a method of modifying the functional characteristics of a protein including providing a protein and reacting the protein with a glycosylated methanethiosulfonate reagent under conditions effective to produce a glycoprotein with altered functional characteristics as compared to the protein. In addition, the present invention relates to methods of determining the structure-function relationships of chemically modified mutant proteins. The present invention also relates to synthetic methods for producing thio-glycoses, the thio-glycoses so produced, and to methods for producing glycodendrimer reagents.

Glycosylimidates, 8. - Synthesis of 1-Thioglycosides

As expected, the reactive acetyl-protected O-(α-D-glucopyranosyl) trichloroacetimidate 3 reacts with S-nucleophiles and trifluoroborane-ether as catalyst to yield exclusively 1-thio-β-D-glucopyranosides with inversion of the configuration.The corresponding benzyl-protected α-trichloroacetimidate 4 affords with retention of the configuration alkyl 1-thio-α-D-glucopyranosides.The importance of alkyl 1-thio-β-D-galactopyranosides in enzyme induction was reason to apply this convenient and efficient glycosyl-transfer reaction to the synthesis of isopropyl 1-thio-β-D-galactopyranoside (12a) and the sodium salt of 1-thio-β-D-galactopyranose (12b), respectively.