20818-25-1Relevant articles and documents
β-D-glucosyl and α-D-galactosyl yariv reagents: Syntheses from p-nitrophenyl-D-glycosides by transfer reduction using ammonium formate
Basile, Dominick V.,Ganjian, Iraj
, p. 7453 - 7456 (2004)
Yariv β-D-glucosyl (4a) and Yariv α-D-galactosyl (4b) reagents are multivalent phenylglycosides. The β-D-glucosyl reagent is considered diagnostic for arabinogalactan proteins (AGPs) to which it can reversibly bind, stain, and precipitate. The α-D-galacto
Self-assembling structures of long-chain phenyl glucoside influenced by the introduction of double bonds
Jung, Jong Hwa,John, George,Yoshida, Kaname,Shimizu, Toshimi
, p. 10674 - 10675 (2002)
Four long-chain phenyl glucoside amphiphiles possessing a saturated or unsaturated long alkyl chain group as the self-assembling unit of a highly organized molecular architecture were synthesized. Their self-assembling properties were investigated by EF-T
Molecularly Imprinted Synthetic Glucosidase for the Hydrolysis of Cellulose in Aqueous and Nonaqueous Solutions
Li, Xiaowei,Zangiabadi, Milad,Zhao, Yan
, p. 5172 - 5181 (2021)
Molecular imprinting is a powerful and yet simple method to create multifunctional binding sites within a cross-linked polymer network. We report a new class of synthetic glucosidase prepared through molecular imprinting and postfunctionalization of cross-linked surfactant micelles. These catalysts are protein-sized water-soluble nanoparticles that can be modified in multiple ways. As their natural counterparts, they bind a glucose-containing oligo- or polysaccharide. They contain acidic groups near the glycosidic bond to be cleaved, with the number and distance of the acid groups tuned systematically. Hydrolysis of cellulose in a key step in biomass conversion but is hampered by the incalcitrance of the highly crystalline cellulose fibers. The synthetic glucosidases are shown to hydrolyze cellobiose and cellulose under a variety of conditions. The best catalyst, with a biomimetic double acid catalytic motif, can hydrolyze cellulose with one-fifth of the activity of commercial cellulases in aqueous buffer. As a highly cross-linked polymeric nanoparticle, the synthetic catalyst is stable at elevated temperatures in both aqueous and nonaqueous solvents. In a polar aprotic solvent/ionic liquid mixture, it hydrolyzes cellulose several times faster than commercial cellulases in aqueous buffer. When deposited on magnetic nanoparticles, it retains 75% of its activity after 10 cycles of usage.
Direct sol-gel replication of the self-assembled nanostructure modified with H-bond functionalities
Jung, Jong Hwa,Shimizu, Toshimi
, p. 1246 - 1247 (2002)
The glucopyranoside-based amphiphile 1 formed nanofiber structures with 25-100 nm of diameters and several micrometer lengths in the presence of aminophenyl glucopyranoside 2, and their self-assembled nanostructures were successfully replicated into the s
Enzymatic Synthesis of a Series of Thioglycosides: Analogs of Arbutin with Efficient Antipigmentation Properties
Daniellou, Richard,Didak, Blanka,Guillotin, Laure,Lafite, Pierre,Landemarre, Ludovic,Lemiègre, Lo?c,Peyrot, Cédric
, p. 3812 - 3818 (2021/08/24)
Arbutin, a natural glycoside, is well known as a commercial tyrosinase inhibitor, and thus, to prevent pigmentary disorders of skin. In fact, tyrosinase is involved in the biosynthesis of melanin, the skin main pigment. However, arbutin is subject to hydr
An Improved Protocol for the Synthesis and Purification of Yariv Reagents
Hoshing, Raghuraj,Saladino, Michael,Kuhn, Helene,Caianiello, David,Lusi, Robert F.,Basu, Amit
, p. 16236 - 16242 (2020/11/20)
Yariv reagents are glycoconjugate tris-azo dyes widely used in plant biology. These reagents are synthesized by diazo coupling between phloroglucinol and a para-diazophenyl glycoside. Despite their synthetic accessibility, well-defined protocols for obtai
Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent
Wadzinski, Tyler J.,Steinauer, Angela,Hie, Liana,Pelletier, Guillaume,Schepartz, Alanna,Miller, Scott J.
, p. 644 - 652 (2018/05/04)
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.
Iron and palladium(II) phthalocyanines as recyclable catalysts for reduction of nitroarenes
Verma, Praveen Kumar,Bala, Manju,Thakur, Kavita,Sharma, Upendra,Kumar, Neeraj,Singh, Bikram
, p. 1258 - 1267 (2014/07/21)
Iron(II) and palladium(II) phthalocyanines have been established as recyclable heterogeneous catalysts for the reduction of aromatic nitro compounds to corresponding amines using diphenylsilane/sodium borohydride as hydrogen sources in ethanol. Various reducible functional groups, such as acetyl, ester, cyano, amide, sulphonamide and carboxylic acid etc. were well tolerated, and the methods were applicable up to gram scale. Mechanistic studies showed that reduction of nitro group proceed through direct (nitroso) pathway and possibly iron or palladium phthalocyanines activates nitro group for reduction. FePc and PdPc also catalyzed the generation of hydrogen from the combination of diphenylsilane/sodium borohydride and ethanol.
Carbohydrate coatings via aryldiazonium chemistry for surface biomimicry
Jayasundara, Dilushan R.,Duff, Thomas,Angione, M. Daniela,Bourke, Jean,Murphy, Deirdre M.,Scanlan, Eoin M.,Colavita, Paula E.
, p. 4122 - 4128 (2013/11/19)
Carbohydrates are extremely important biomolecules and their immobilization onto solid surfaces is of interest for the development of new biomimetic materials and of new methods for understanding processes in glycobiology. We have developed an efficient surface modification methodology for the functionalization of a range of materials with biologically active carbohydrates based on aryldiazonium chemistry. We describe the synthesis and characterization of carbohydrate reagents, which were subsequently employed for the one-step, solution-based modification of carbon, metals, and alloys with monosaccharides. We used a combination of spectroscopic and nanogravimetric methods to characterize the structure of the carbohydrate layers; we report an average surface coverage of 7.8 × 10-10 mol cm-2 under our experimental conditions. Concanavalin A, a mannose-binding lectin, and Peanut Agglutinin, a galactose-binding lectin, were found to bind from solution to their respective monosaccharide binding partners immobilized at the surface. This result suggests that the spontaneous chemisorption of aryldiazonium monosaccharide precursors leads to the formation of monosaccharide layers that retain the biological recognition specificity of the parent carbohydrate molecule. Finally, we carried out measurements using fluorescently labeled Bovine Serum Albumin (BSA) and found that these carbohydrate coatings reduce unspecific adsorption of this protein at carbon surfaces. These results suggest that aryldiazonium-derived carbohydrate coatings may offer a promising strategy for preventing undesirable protein accumulation onto surfaces.
A novel d-glucose derivative radiolabeled with technetium-99m: Synthesis, biodistribution studies and scintigraphic images in an experimental model of Ehrlich tumor
de Barros, André Luís Branco,Cardoso, Valbert Nascimento,Mota, Luciene das Gra?as,Leite, Elaine Amaral,de Oliveira, M?nica Cristina,Alves, Ricardo José
scheme or table, p. 2478 - 2480 (2010/07/06)
A d-glucose-MAG3 derivative was successfully synthesized and radiolabeled in high labeling yield. Biodistribution studies and scintigraphic images in Ehrlich tumor-bearing mice were performed. This compound showed high accumulation in tumor tis
