4756-30-3

Usage

Uses

Used in Research and Pharmaceutical Applications:
4'-Chlorophenyl-beta-D-glucopyranoside serves as a substrate for enzymes involved in sugar metabolism, making it instrumental in the study and understanding of these metabolic processes. Its unique structure allows researchers to investigate the specific interactions and mechanisms of enzymes with sugar molecules.
Used as a Reference Standard in Analytical Methods:
In the field of carbohydrate chemistry, 4'-chlorophenyl-beta-D-glucopyranoside is utilized as a reference standard for analytical methods. Its distinct properties and reactivity enable accurate comparisons and measurements, ensuring the reliability and precision of analytical techniques.
Used in Drug Development and Medicinal Chemistry:
Due to its ability to interact with biological systems, 4'-chlorophenyl-beta-D-glucopyranoside holds potential in drug development and medicinal chemistry. Its unique structure and reactivity can be leveraged to design and develop new pharmaceutical compounds with targeted therapeutic effects.
Used in Enzyme Reactivity and Selectivity Studies:
The presence of the chlorophenyl group in 4'-chlorophenyl-beta-D-glucopyranoside makes it particularly useful for studying the reactivity and selectivity of various enzymes. This knowledge can contribute to the advancement of enzyme-based therapies and the development of more efficient biocatalysts.

Upstream product

• 5041-92-9 p-chlorophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 106-48-9 4-chloro-phenol 
• 2106-10-7 1-deoxy-1-fluoro-α-D-glucose 

Downstream Products

• 107807-32-9 p-chlorophenyl 2-O-β-D-mannopyranosyl-β-D-mannopyranoside 
• 107807-31-8 p-chlorophenyl 6-O-β-D-mannopyranosyl-β-D-mannopyranoside 
• 2280-44-6 D-Glucose 
• 106-48-9 4-chloro-phenol 
• 24573-38-4 4-chlorophenolate 

Relevant academic research and scientific papers

Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent

Glycosylated natural products and synthetic glycopeptides represent a significant and growing source of biochemical probes and therapeutic agents. However, methods that enable the aqueous glycosylation of endogenous amino acid functionality in peptides without the use of protecting groups are scarce. Here, we report a transformation that facilitates the efficient aqueous O-glycosylation of phenolic functionality in a wide range of small molecules, unprotected tyrosine, and tyrosine residues embedded within a range of complex, fully unprotected peptides. The transformation, which uses glycosyl fluoride donors and is promoted by Ca(OH)2, proceeds rapidly at room temperature in water, with good yields and selective formation of unique anomeric products depending on the stereochemistry of the glycosyl donor. High functional group tolerance is observed, and the phenol glycosylation occurs selectively in the presence of virtually all side chains of the proteinogenic amino acids with the singular exception of Cys. This method offers a highly selective, efficient, and operationally simple approach for the protecting-group-free synthesis of O-aryl glycosides and Tyr-O-glycosylated peptides in water.

Toxicity and metabolism of p-chlorophenol in the marine microalga Tetraselmis marina

Toxicity and metabolism of para-chlorophenol (p-CP) in the marine microalga Tetraselmis marina have been studied. The inhibition constant EC50 for p-CP was 272 ± 17 μM (34.8 ± 2.2 mg L-1) under the experimental conditions. Two metabolites were detected in the growth medium in the presence of p-CP by reverse phase HPLC and their concentrations increased at the expense of p-CP. The two metabolites, which were found to be more polar than p-CP, were isolated by a C18 column. They were identified as p-chlorophenyl-β-d-glucopyranoside (p-CPG) and p-chlorophenyl-β-d-(6-O-malonyl)-glucopyranoside (p-CPGM) by electrospray ionization-mass spectrometric analysis in a negative ion mode. The molecular structures of p-CPG and p-CPGM were further confirmed by enzymatic and alkaline hydrolyses. Treatment with β-glucosidase released free p-CP and glucose from p-CPG, whereas p-CPGM was completely resistant. Alkaline hydrolysis completely cleaved the esteric bond of the malonylated glucoconjugate and yielded p-CPG and malonic acid. It was concluded that the pathway of p-CP metabolism in T. marina involves an initial conjugation of p-CP to glucose to form p-chlorophenyl-β-d-glucopyranoside, followed by acylation of the glucoconjugate to form p-chlorophenyl-β-d-(6-O-malonyl)-glucopyranoside. The metabolism of p-CP in T. marina was mainly driven by photosynthesis, and to a lesser extent by anabolic metabolism in the dark. Accordingly, the detoxification rate under light was about seven times higher than in the darkness. This work provides the first evidence that microalgae can adopt a combined glucosyl transfer and malonyl transfer process as a survival strategy for detoxification of such xenobiotics as p-CP.