120095-47-8

Usage

Uses

Used in Organic Chemistry Research:
Phenyl 3,4-O-(1-methylethylidene)-1-thio-beta-D-galactopyranoside is used as a substrate in enzymatic assays for studying glycosylation processes. Its unique structure allows researchers to investigate the mechanisms of enzymatic reactions and develop new methodologies for the synthesis of complex carbohydrates.
Used in Biological Research:
Phenyl 3,4-O-(1-methylethylidene)-1-thio-beta-D-galactopyranoside is used as a valuable tool in biological research to explore the role of galactopyranosides in various biological processes. Its properties enable researchers to gain insights into the functions and interactions of these molecules within living organisms.
Used in Drug Design and Development:
Phenyl 3,4-O-(1-methylethylidene)-1-thio-beta-D-galactopyranoside is utilized in the design and development of potential therapeutic agents targeting glycosylation pathways. Its unique structure and properties make it a promising candidate for creating new drugs that can modulate these pathways and treat related diseases.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Phenyl 3,4-O-(1-methylethylidene)-1-thio-beta-D-galactopyranoside is used as a key intermediate in the synthesis of complex carbohydrate-based drugs. Its unique structure and properties make it an essential component in the development of novel therapeutic agents with potential applications in various diseases.
Used in Academic Research:
In academic research, Phenyl 3,4-O-(1-methylethylidene)-1-thio-beta-D-galactopyranoside is used as a model substrate for studying the specificity and efficiency of glycosyltransferases and other enzymes involved in glycosylation. It helps researchers understand the enzyme-substrate interactions and develop new strategies for enzyme engineering and optimization.

Upstream product

• 124476-99-9 phenyl 2,6-di-O-acetyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 124477-00-5 phenyl 2,6-di-O-benzoyl-3,4-O-(isopropylidene)-1-thio-β-D-galactopyranoside 
• 270075-72-4 phenyl 1-thio-3,4-O-isopropylidene-6-O-(1-methoxyl-1-methylethyl)-β-D-galactopyranoside 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 77-76-9 2,2-dimethoxy-propane 
• 67-64-1 acetone 
• 116-11-0 2-Methoxypropene 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 25878-60-8 D-galactose pentaacetate 
• 108-98-5 thiophenol 
• 4163-60-4 β-D-galactose peracetate 
• 10257-28-0 D-Galactose 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 

Downstream Products

• 214468-37-8 phenyl 6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 848568-09-2 phenyl 6-O-benzoyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 258286-51-0 phenyl (6-O-benzyl-2-O-benzoyl-1-thio-β-D-galactopyranoside) 
• 478687-05-7 phenyl 4-O-acetyl-2,6-di-O-benzyl-1-thio-β-D-galactopyranoside 
• 173029-40-8 N-trichloroethoxycarbonyl-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-L-serine benzyl ester 
• 173029-39-5 N-trichloroethoxycarbonyl-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-L-serine benzyl ester 
• 144781-45-3 phenyl 2,3,6-tri-O-benzyl-1-thio-β-D-galactopyranoside 

Relevant academic research and scientific papers

Nano n-propylsulfonated magnetic γ-Fe 2O 3 as an efficient and reusable catalyst for the synthesis O-isopropylidene derivatives of carbohydrates

Nano n-propylsulfonated γ-Fe2O3 was found to be a highly efficient, reusable heterogeneous catalyst for the conversion of a range of monosaccharides and some of their derivatives to the corresponding O-isopropylidene derivatives in good to excellent yields by refluxing the reaction mixture in dry acetone. The magnetic property of the catalyst enabled its separation from the reaction mixture by a simple process of filtration along with the aid of an external magnet. The efficiency of the catalyst was found to be largely unaffected for at least up to six cycles of reuse, thus proving the new methodology to be environmentally rewarding besides being simple and facile in operation.

Carbohydrate-Based NK1R Antagonists with Broad-Spectrum Anticancer Activity

NK1R antagonists, investigated for the treatment of several pathologies, have shown encouraging results in the treatment of several cancers. In the present study, we report on the synthesis of carbohydrate-based NK1R antagonists and their evaluation as anticancer agents against a wide range of cancer cells. All of the prepared compounds, derived from either-arabinose, have shown high affinity and NK1R antagonistic activity with a broad-spectrum anticancer activity and an important selectivity, comparable to Cisplatin. This strategy has allowed us to identify the galactosyl derivative 14α , as an interesting hit exhibiting significant NK1R antagonist effect (kinact0.209 ± 0.103 μM) and high binding affinity for NK1R (IC50= 50.4 nM,Ki= 22.4 nM by measuring the displacement of [125I] SP from NK1R). Interestingly, this galactosyl derivative has shown marked selective cytotoxic activity against 12 different types of cancer cell lines.

Studies towards the total synthesis of repeating unit of O-sulfated polysaccharide from marine bacterium Cobetia pacifica KMM 3878

Herein we report assembly of the appropriately protected trisaccharide repeating unit of Cobetia pacifica KMM 3878 O-sulfated polysaccharide. Our synthesis involves 3,4-O-pyruvilated galactose as the key building block which acts as a donor as well as acceptor in the construction of trisaccharide. We obtained the R isomer as a major stereoisomer in the pyruvilation reaction. The glycosylations proceeded with high stereo and regioselectivity.

ANTAGONISTS OF NK1 RECEPTORS DERIVED FROM CARBOHYDRATES, PRODUCTION METHOD AND MEDICAL USE

The invention relates to a compound of general formula (I), and to the use thereof in medicine, or for the production of a medicament for the treatment of different diseases, preferably a cancer such as melanoma, lung carcinoma or breast cancer. For this purpose, the invention also relates to a pharmaceutical composition comprising said compound. In addition, the invention relates to a method for producing the compound of general formula (I).

Directing effect by remote electron-withdrawing protecting groups at O-3 or O-4 position of donors in glucosylations and galactosylations

Glucosylations and galactosylations of various acceptors with donors possessing an electron-withdrawing benzylsulfonyl, benzoyl, or acetyl group at the O-3 or O-4 position were performed. A β-directing effect by the benzylsulfonyl group at O-3 of the glucosyl donors and by the benzylsulfonyl and acyl groups at O-4 of the glucosyl donors was observed. In contrast, acyl groups at O-3 of the glucosyl donors and acyl groups at O-3 and O-4 of the galactosyl donors exhibited an α-directing effect. The α-directing effect is partly considered to remote participation of the acyl groups, whereas the β-directing effect is somewhat attributed to the SN2-like reaction of the acceptor with the glycosyl triflate or the contact ion pair, which is stabilized by remote electron-withdrawing groups. Further evidence for the stability of the α-glycosyl triflates was determined by a low-temperature NMR study.

Development of a highly α-selective galactopyranosyl donor based on a rational design

A galactosyl donor was rationally designed based on protecting group-stereoselectivity study. This donor was prepared and tested in a series of glycosylation reaction. Excellent α-selectivity was observed in the test reactions.

Solid-phase carbohydrate synthesis via on-bead protecting group chemistry

Di- and tri-saccharides were synthesized on a solid phase. The procedure started with a non-protected sugar linked via either cysteine or glutamine to a polystyrene resin. Selective dimethoxytritylation chemistry and subsequent steps yielded a resin-bound acceptor that could be glycosylated to yield β1,6-linked disaccharides. Reiteration of the procedure produced the trisaccharide.

O-Isopropylidenation of carbohydrates catalyzed by vanadyl triflate

Vanadyl triflate has been identified as a mild and efficient catalyst for the chemoselective O-isopropylidenation of functionalized carbohydrates with acetone and acetone equivalents. The current protocol is compatible with a diverse array of protecting groups and the products can be readily isolated by simple aqueous wash.

From glycoside hydrolases to thioglycoligases: The synthesis of thioglycosides

The treatment of various glycosyl acceptors, each containing a reactive thiol group, with the appropriate glycosyl donor and a glycoside hydrolase or glycosynthase, failed to yield any thioglycosides - only the products of O-glycosylation were formed. However, thioglycosides were formed when a thioglycoligase was used to mediate the reaction between acceptor and donor. In fact, pyranose acceptors possessing a thiol group at C3, C4 or C6 (but not C2) were all capable of conversion into thioglycosides. Some comment is given regarding the mechanism of the various processes.

The synthesis of deoxy-α-Gal epitope derivatives for the evaluation of an anti-α-Gal antibody binding

α-Gal epitopes (also termed as α-Gal) are carbohydrate structures bearing the α-D-Gal-(1→3)-β-D-Gal terminus 1 and are known to be the antigen responsible for antibody-mediated hyperacute rejection in xenotransplantation. Terminal 2-, 3-, 4-, and 6-deoxy-Gal derivatives of α-Gal were synthesized. Inhibition ELISA using mouse laminin was established to determine the binding affinity of the synthesized α-Gal derivatives. 4-Deoxy-α-Gal derivative 7 showed a significant reduction in antibody recognition. The IC50 value was 15-fold poorer than the standard α-Gal epitopes α-D-Gal-(1→3)-β-D-Gal-(1→4)-β-D-Glc-NHAc (39) and α-D-Gal-(1→3)-β-D-Gal-(1→4)-β-D-Glc-OBn (40). A similar observation was seen with 2-deoxy-α-Gal derivative 5, whose IC50 value was nearly tenfold higher than the standards. Interestingly, substitution at the terminal 3-position resulted in only a fourfold decrease in antibody recognition, suggesting a possible point of future derivation. Finally, 6-deoxy-α-Gal derivative 8 exhibited similar antibody recognition to both α-Gal epitope 39 and α-Gal epitope 40. This strongly suggests that derivatization at the 6-position can be accomplished without loss of antibody recognition. These findings can be utilized for the future design of other α-Gal derivatives.