130263-77-3

Usage

Uses

Used in Organic Synthesis:
2-Mercaptoethyl -D-glucopyranoside is used as a key intermediate in organic synthesis for its ability to facilitate the formation of complex organic molecules. Its unique structure allows it to participate in a variety of chemical reactions, contributing to the development of new compounds with potential applications across different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Mercaptoethyl -D-glucopyranoside is used as a building block for the synthesis of pharmaceutical compounds. Its reactivity and functional groups make it suitable for the creation of new drug candidates, potentially leading to the discovery of novel treatments and therapies.
Used in Chemical Research:
2-Mercaptoethyl -D-glucopyranoside is also utilized in chemical research as a model compound to study various reaction mechanisms and to develop new synthetic methodologies. Its properties and reactivity provide valuable insights into the behavior of similar compounds, furthering the understanding of organic chemistry.
Overall, 2-Mercaptoethyl -D-glucopyranoside is a versatile compound with applications in organic synthesis, pharmaceutical development, and chemical research, showcasing its importance in the advancement of scientific knowledge and the creation of innovative products.

Upstream product

• 10257-28-0 D-Galactose 
• 60-24-2 2-hydroxyethanethiol 
• 358750-84-2 2-thioethyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 849420-02-6 (2-chloroethyl)-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 110891-64-0 2'-bromoethyl-α-D-mannopyranoside 
• 7296-15-3 alpha-D-mannopyranoside 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 16977-78-9 2'-bromoethyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 212309-05-2 2-(acetylthio)ethyl tetra-O-acetyl-α-D-mannopyranoside 
• 59-23-4 D-Galactose 
• 250358-65-7 2-bromoethyl α-D-galactopyranoside 
• 86651-40-3 2'-bromoethyl-2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 
• 3646-73-9 α-D-galactopyranose 
• 250358-66-8 2 '-thioethyl-α-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis of Clustered Glycoside - Antigen Conjugates by Two One-Pot, Orthogonal, Chemoselective Ligation Reactions: Scope and Limitations

Major histocompatibility class II antigens have been bound to clustered glycosides for selective targeting of the dendritic cell mannose receptor. Di-, tetra-, and octavalent glycoside - antigen conjugates have been obtained after two, orthogonal, hydrazo

Galactosylation of thiol group by beta-galactosidase.

beta-Galactosidase catalyzed beta-galactosylation not only of a hydroxyl group but also of a thiol group in the condensation reaction of D-galactose and 2-mercaptoethanol. The thio-galactosylation product was confirmed as 2-hydroxyethyl S-beta-D-galactoside on the bases of fast atom bombardment mass spectrometry, infrared spectroscopy, and nuclear magnetic resonance spectorometry. Aspergillus oryzae beta-galactosidase hydrolyzed p-nitrophenyl S-beta-D-galactoside most rapidly among several beta-galactosidases and produced the thio-galactosylation product most efficiently. The Penicillim multicolor enzyme was as effective as the A. oryzae enzyme. However the enzymes from Escherichia coli, Saccharomyces fragilis, Kluyveromyces lactis, and Bacillus circulans galactosylated hydroxyl groups predominantly to produce O-galactoside. The thio-galactoside was synthesized most effectively at a 2-mercaptoethanol concentration of about 1.25 M. Galactose concentration at 0.8-2.8 M did not affect the synthetic yield of the thiogalactoside so greatly.

Glucose- and pH-responsive controlled release of cargo from protein-gated carbohydrate-functionalized mesoporous silica nanocontainers

Learning to let go: Controlled release of cargo (purple cubes) from lectin (blue squares)-gated nanopores was achieved using mannose (green loops)-functionalized mesoporous silica (see scheme). The protein nanogates could be opened either by decreasing the pH of the buffer or by adding competing glucose (yellow rings) to release the cargo from the pores. Copyright

NANOPARTICLE-BASED THERAPY OF INFLAMMATORY DISORDERS

The present invention provides a nanoparticle comprising: a core comprising a metal and/or a semiconductor; and a plurality of ligands covalently linked to the core, wherein said ligands comprise: (i) at least one dilution ligand comprising a carbohydrate, glutathione or a polyethyleneglycol moiety; and (ii) a ligand of the formula MTX-L-, wherein MTX-L-represents methotrexate coupled to said core via a linker L. Also provided are pharmaceutical compositions of the nanoparticle, including gel formulations, and medical uses of the nanoparticle and pharmaceutical compositions, including for the treatment of an inflammatory or autoimmune disorder, such as psoriasis.

ANTIFOLATE-CARRYING NANOPARTICLES AND THEIR USE IN MEDICINE

The present invention provides a nanoparticle comprising: a core comprising a metal and/or a semiconductor; and a plurality of ligands covalently linked to the core, wherein said ligands comprise: (i) at least one dilution ligand comprising a carbohydrate, glutathione or an ethylene glycol-containing moiety; and (ii) a ligand of the formula D-L1-Z-L2, wherein D comprises an antifolate drug or folic acid, L1 comprises a first linker portion comprising a C2-C12 glycol and/or C2-C12 alkyl chain, L2 comprises a second linker portion comprising a C2-C12 glycol and/or C2-C12 alkyl chain, wherein L1 and L2 may be the same or different, and wherein Z represents a carbonyl-containing group linking L1 and L2, and wherein L2 is coupled to said core, Also provided are pharmaceutical compositions comprising such nanoparticles, medical uses thereof and methods for producing the nanoparticles.

An Efficient Method for the Conjugation of Hydrophilic and Hydrophobic Components by Solid-Phase-Assisted Disulfide Ligation

Chemical conjugation between hydrophilic and hydrophobic components is difficult because of their extremely different solubility. Herein, we report a new versatile method with a solid-phase-assisted disulfide ligation to overcome the difficulty of conjugation attributed to solubility. The method involves two steps in a one-pot process: 1) loading of a hydrophobic molecule onto a resin in an organic solvent, and 2) release of the solid-supported hydrophobic molecule as a conjugate with a hydrophilic molecule into an aqueous solvent. This strategy allows the use of a suitable solvent system for the substrates in each step. Conjugates of a water-insoluble drug, plinabulin, with hydrophilic carriers that could not be prepared by solution-phase reactions were obtained in moderate yields (29–45 %). This strategy is widely applicable to the conjugation of compounds with solubility problems.

A Bifunctional Spin Label for Ligand Recognition on Surfaces

In situ monitoring of biomolecular recognition, especially at surfaces, still presents a significant technical challenge. Electron paramagnetic resonance (EPR) of biomolecules spin-labeled with nitroxides can offer uniquely sensitive and selective insights into these processes, but new spin-labeling strategies are needed. The synthesis and study of a bromoacrylaldehyde spin label (BASL), which features two attachment points with orthogonal reactivity is reported. The first examples of mannose and biotin ligands coupled to aqueous carboxy-functionalized gold nanoparticles through a spin label are presented. EPR spectra were obtained for the spin-labeled ligands both free in solution and attached to nanoparticles. The labels were recognized by the mannose-binding lectin, Con A, and the biotin-binding protein avidin-peroxidase. Binding gave quantifiable changes in the EPR spectra from which binding profiles could be obtained that reflect the strength of binding in each case.

NANOPARTICLES AND THEIR USE IN CANCER THERAPY

The present invention provides a nanoparticle comprising a core comprising a metal; and a corona comprising a plurality of ligands covalently linked to the core, the plurality of ligands including at least a first species of ligand comprising an ethylene glycol portion and an amine group and at least a second species of ligand comprising a carbohydrate group, for use in a method of treating a cancer, particularly skin cancer, in a mammalian subject. Also disclosed are methods of treatment by administering the nanoparticles alone or in combination with radiotherapy.

COMBINATION PEPTIDE-NANOPARTICLES AND DELIVERY SYSTEMS INCORPORATING SAME

Nanoparticles having a core and a corona of ligands covalently linked to the core, wherein differing species of peptides are bound to the nanoparticles and incorporated into various dosage forms.

NANOPARTICLE PEPTIDE COMPOSITIONS

The present invention relates to amylin peptide-carrying nanoparticles, particularly for use in medicine, and includes methods for treatment of disorders, e.g., of blood glucose regulation. Nanoparticle composition comprise a nanoparticle comprising a core comprising a metal and/or a semiconductor; and a corona comprising a plurality of ligands covalently linked to the core, wherein said ligands comprise glutathione; and at least one amylin peptide that is non-covalently bound to the corona.