121238-27-5Relevant articles and documents
Synthesis of bifunctional cationic compound for gene delivery
Ren, Tan,Zhang, Guisheng,Liu, Dexi
, p. 1007 - 1010 (2001)
Bifunctional cationic compound carrying trivalent galactosides as the cell targeting ligand and DAB-dendr-(NH2)8 (generation 2.0) as the DNA binding domain was synthesized for gene delivery to hepatocytes. DAB-dendr-(NH2)4 (generation 1.0) conjugated with a hydrocarbon chain was used as a scaffold for the attachment of three galactosides, while the other hydrocarbon end was linked with DAB-dendr-(NH2)8 (generation 2.0) through a carbamate bond. This design provided an effective entry for the synthesis of a polyamine compound having the cell targeting galactosyl ligand. Preliminary in vitro transfection results demonstrated that the bifunctional cationic compound could effectively deliver the gene into HepG2 cells.
Developing a library of mannose-based mono-and disaccharides: A general chemoenzymatic approach to monohydroxylated building blocks
Bavaro, Teodora,Marzatico, Sara,Recca, Teresa,Robescu, Marina Simona,Tanzi, Lisa,Terreni, Marco,Zhang, Yongmin
, (2020)
Regioselective deprotection of acetylated mannose-based mono-and disaccharides differently functionalized in anomeric position was achieved by enzymatic hydrolysis. Candida rugosa lipase (CRL) and Bacillus pumilus acetyl xylan esterase (AXE) were immobilized on octyl-Sepharose and glyoxyl-agarose, respectively. The regioselectivity of the biocatalysts was affected by the sugar structure and functionalization in anomeric position. Generally, CRL was able to catalyze regioselective deprotection of acetylated monosaccharides in C6 position. When acetylated disaccharides were used as substrates, AXE exhibited a marked preference for the C2, or C6 position when C2 was involved in the glycosidic bond. By selecting the best enzyme for each substrate in terms of activity and regioselectivity, we prepared a small library of differently monohydroxylated building blocks that could be used as intermediates for the synthesis of mannosylated glycoconjugate vaccines targeting mannose receptors of antigen presenting cells.
Efficient synthesis and activity of beneficial intestinal flora of two lactulose-derived oligosaccharides
Zhu, Zhen-Yuan,Cui, Di,Gao, Hui,Dong, Feng-Ying,Liu, Xiao-Cui,Liu, Fei,Chen, Lu,Zhang, Yong-Min
, p. 8 - 13 (2016)
Lactulose is considered as a prebiotic because it promotes the intestinal proliferation of Lactobacillus acidophilus which is added to various milk products. Moreover, lactulose is used in pharmaceuticals as a gentle laxative and to treat hyperammonemia. This study was aimed at the total synthesis of two Lactulose-derived oligosaccharides: one is 3-O-β-d-galactopyranosyl-d-fructose, d-fructose and β-d-galactose bounded together with β-1,3-glycosidic bound, the other is 1-O-β-d-galactopyranosyl-d-fructose, d-fructose and β-d-galactose bounded together with β-1,1-glycosidic bound, which were accomplished in seven steps from d-fructose and β-d-galactose and every step of yield above 75%. This synthetic route provided a practical and effective synthetic strategy for galactooligosaccharides, starting from commercially available monosaccharides. Then we evaluated on their prebiotic properties in the search for potential agents of regulating and improving the intestinal flora of human. The result showed that the prebiotic properties of Lactulose-derived oligosaccharides was much better than Lactulose. Among them, 3-O-β-d-galactopyranosyl-d-fructose displayed the most potent activity of proliferation of L. acidophilus.
A study of polymer-supported bases for the solution phase synthesis of glycosyl trichloroacetimidates
Chiara, Jose Luis,Encinas, Lourdes,Díaz, Beatriz
, p. 2445 - 2448 (2005)
Polystyrene-supported strong organic bases are highly efficient reagents for the solution-phase synthesis of glycosyl trichloroacetimidates, affording quantitative yields of pure products in short reaction times after simple filtration and evaporation. Al
Glycopolymer-Grafted Nanoparticles: Synthesis Using RAFT Polymerization and Binding Study with Lectin
Kutcherlapati, S. N. Raju,Koyilapu, Rambabu,Boddu, Uma Maheswara Rao,Datta, Debparna,Perali, Ramu Sridhar,Swamy, Musti J.,Jana, Tushar
, p. 7309 - 7320 (2017)
The weak binding between carbohydrates and proteins is a major constraint toward the development of carbohydrate-based therapeutics. To address this, here we report the synthesis of glycopolymer (GP)-grafted silica nanoparticles (SiNP) by using reversible addition-fragmentation chain transfer (RAFT) polymerization through the grafting-from approach using a multistep process. GP chains of various lengths with controlled molecular weight and narrow polydispersities were grown on the RAFT agent anchored SiNP surface using mannosyloxyethyl methacrylate (MEMA) as a glycomonomer. Spectroscopic (FT-IR, NMR) and thermogravimetric studies confirmed the grafting of poly(MEMA) chains on the SiNP surface and also showed that the dry DMF is a better solvent as compared to water/ethanol mixture for carrying out the MEMA polymerization on SiNP surface. The mean diameter of the dry GP-grafted SiNPs (GP-g-SiNPs) obtained from microscopic studies was in the range 50-60 nm, whereas the hydrodynamic diameter as obtained using light scattering measurements varied between 90 and 165 nm depending on the chain length of poly(MEMA). Hydrolysis of silica cores using aqueous HF enabled characterization of cleaved polymer using GPC, and the obtained unimodal chromatogram and narrow PDI confirmed that the polymerization proceeded through the RAFT mechanism. GP-g-SiNPs displayed stronger binding to the mannose specific lectin, Concanavalin A, owing to the larger positive binding entropic contribution which resulted in an association constant that is 800- and 400-fold stronger than that of monomeric mannose and GP chains, respectively.
1,2,3,4-TETRAHYDROQUINOXALINE DERIVATIVE, PREPARATION METHOD THEREFOR AND APPLICATION THEREOF
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, (2022/01/24)
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An alternative approach for the synthesis of sulfoquinovosyldiacylglycerol
Domey, Hendrik,Fischer, Judith,Rohn, Sascha,Sitz, Tobias
, (2021/07/28)
Sulfoquinovosyldiacylglycerol (SQDG) is a glycolipid ubiquitously found in photosyn-thetically active organisms. It has attracted much attention in recent years due to its biological ac-tivities. Similarly, the increasing demand for vegan and functional foods has led to a growing interest in micronutrients such as sulfolipids and their physiological influence on human health. To study this influence, reference materials are needed for developing new analytical methods and providing enough material for model studies on the biological activity. However, the availability of these materials is limited by the difficulty to isolate and purify sulfolipids from natural sources and the unavailability of chemical standards on the market. Consequently, an alternative synthetic route for the comprehensive preparation of sulfolipids was established. Here, the synthesis of a sulfolipid with two identical saturated fatty acids is described exemplarily. The method opens possibilities for the preparation of a diverse range of interesting derivatives with different saturated and unsatu-rated fatty acids.