10294-12-9Relevant academic research and scientific papers
Development of regioselective deacylation of peracetylated β-d-monosaccharides using lipase from Pseudomonas stutzeri under sustainable conditions
Sandoval,Hoyos,Corts,Bavaro,Terreni,Herniz
, p. 55495 - 55502 (2014)
The lipase-catalyzed regioselective deacylation of peracetylated pyranosides has been evaluated in biosolvents. Among the biocatalysts tested, lipase from Pseudomonas stutzeri showed the highest activity, displaying regiospecific activity towards the anomeric position. This lipase was also employed in the regioselective alcoholysis of peracetylated sugars in green solvents, contributing to improve the sustainability of the process. Yields up to 97% of the desired product with different biosolvents were found. These reactions took place without noticeable activity and with total regioselectivity, representing a considerable improvement over the use of an aqueous buffer or conventional organic solvents. Furthermore, scaled up reactions are feasible without losing catalytic action. In order to understand the role of these biosolvents in the enzyme's synthetic behaviour, molecular modelling and docking studies were performed in the presence of some selected biosolvents to conclude that the presence of biosolvents in the reaction media modifies the access of the alcohols to the enzymatic active site allowing the presence of small alcohols and not i-propyl and t-butyl residues in the alcohol. This journal is
One-pot synthesis of per-O-acetylated hemiacetals from free sugars in a deep eutectic solvent
Rokade, Sunil M.,Bhate, Prakash M.
, p. 21 - 23 (2015)
Free sugars reacted with acetic anhydride in a deep eutectic solvent made from choline chloride and ZnCl2 at 90°C to afford the corresponding peracetates that on further heating to 100°C underwent selective deacetylation at the anomeric position to furnish the corresponding peracetylated hemiacetals in good yield.
NEW METHOD FOR THE 1-DEACETYLATION OF PERACETATES OF AMINOSUGARS
Pertel', S.S.,Chirva, V.Ya.
, p. 160 - 161 (1994)
A method for the selective O-deacetylation at the glycosidic centers of aminosugar peracetates is proposed.
Synthesis, Characterization, X-Ray Crystallography, and Antileishmanial Activities of N-Linked and O-Linked Glycopyranosides
Rashid, Haroon Ur,Khan, Sher Wali,Khan, Momin,Nadhman, Akhtar,Rehman, Noor,Tariq, Muhammad,Yousuf, Sammer
, (2018)
Novel N-linked 5a-e and O-linked glycopyranosides 7a-e were synthesized in high yield from commercially available L-tartaric acid containing two asymmetric centers and C2 axis of symmetry. The compound L-tartaric acid was completely protected and then partially hydrolyzed to get the monoester, which upon treatment with different amino and hydroxyl derivatives of glycopyranoses gave the desired amides and esters. The synthesized derivatives were purified by chromatography and characterized by spectroanalytical techniques. The structure of compound 7c in the series was supported by X-ray analysis. Leishmanicidal activities of compounds 5a-e and 7a-e were investigated which showed moderate to good activities.
Enzymes in Carbohydrate Synthesis: Lipase-Catalyzed Selective Acylation and Deacylation of Furanose and Pyranose Derivatives
Hennen, William J.,Sweers, H. Marcel,Wang, Yi-Fong,Wong, Chi-Huey
, p. 4939 - 4945 (1988)
A number of furanose and pyranose derivatives were selectively acylated and deacylated on a preparative scale in lipase-catalyzed reactions.The primary hydroxyl functions of the methyl furanosides of D-ribose, D-arabinose, D-xylose, and 2-deoxy-D-ribose were selectively acetylated by crude porcine pancreatic lipase in tetrahydrofuran by using 2,2,2-trifluoroethyl acetate as the acyl donor.Selective deacetylations of the primary hydroxyl functions in the peracetylated methyl furanosides of D-ribose, D-arabinose, D-xylose, and 2-deoxy-D-ribose were best accomplished in a 9:1 solution of 0.1 N phosphate buffer (pH 7) and N,N-dimethylformamide using Candida cylindracea lipase.Selective cleavage of the 1-O-acetyl groups from 1,2,3,5-tetra-O-acetyl-D-ribose and -D-xylose were similarly accomplished with Aspergillus niger lipase.Similar regioselectivites were observed in the pyranose series.The Candida lipase was found to be the best for selective deacylation of the primary position from the peracylated methyl pyranosides, and porcine pancreatic lipase was the best for selective hydrolysis of the 1-O-acetyl groups from peracetylated pyranoses.
A useful method for deprotection of the protective allyl group at the anomeric oxygen of carbohydrate moieites using tetrakis(triphenylphosphine)palladium
Nakayama,Uoto,Higashi,Soga,Kusama
, p. 1718 - 1720 (1992)
We have developed a simple method for the deprotection of allyl groups used as a protective group for the anomeric oxygen on a sugar moiety by employing tetrakis(triphenylphosphine) palladium in acetic acid. This method is applicable for not only simple but also complex allyl glycosides, such as natural lipid A intermediates and other important lipid A intermediates. Further, this method would be useful for large-scale preparation.
Design of a "turn-off/turn-on" biosensor: Understanding carbohydrate-lectin interactions for use in noncovalent drug delivery
Gorityala, Bala Kishan,Lu, Zhiqiang,Leow, Min Li,Ma, Jimei,Liu, Xue-Wei
, p. 15229 - 15232 (2012)
A low-cost and highly sensitive biosensor system is designed to investigate carbohydrate-lectin interactions. This combination of glyco-gold nanoparticles and boronic acid biosensor system opens a way to study noncovalent drug delivery.
Synthesis and Antitubercular and Antibacterial Activities of Triethylammonium 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosyl Decyl Phosphate
Garifullin,Sharipova,Voloshina,Kravchenko,Kataev
, p. 1333 - 1336 (2018)
Phosphorylation of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucose at the anomeric hydroxy group gave previously unknown triethylammonium 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosyl phosphonate, and successive treatment of the latter with decan-1-ol and aqueous iodine afforded triethylammonium 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl phosphate.
Galactose Derivative-Modified Nanoparticles for Efficient siRNA Delivery to Hepatocellular Carcinoma
Huang, Kuan-Wei,Lai, Yu-Tsung,Chern, Guann-Jen,Huang, Shao-Feng,Tsai, Chia-Lung,Sung, Yun-Chieh,Chiang, Cheng-Chin,Hwang, Pi-Bei,Ho, Ting-Lun,Huang, Rui-Lin,Shiue, Ting-Yun,Chen, Yunching,Wang, Sheng-Kai
, p. 2330 - 2339 (2018)
Successful siRNA therapy requires suitable delivery systems with targeting moieties such as small molecules, peptides, antibodies, or aptamers. Galactose (Gal) residues recognized by the asialoglycoprotein receptor (ASGPR) can serve as potent targeting moieties for hepatocellular carcinoma (HCC) cells. However, efficient targeting to HCC via galactose moieties rather than normal liver tissues in HCC patients remains a challenge. To achieve more efficient siRNA delivery in HCC, we synthesized various galactoside derivatives and investigated the siRNA delivery capability of nanoparticles modified with those galactoside derivatives. In this study, we assembled lipid/calcium/phosphate nanoparticles (LCP NPs) conjugated with eight types of galactoside derivatives and demonstrated that phenyl β-d-galactoside-decorated LCP NPs (L4-LCP NPs) exhibited a superior siRNA delivery into HCC cells compared to normal hepatocytes. VEGF siRNAs delivered by L4-LCP NPs downregulated VEGF expression in HCC in vitro and in vivo and led to a potent antiangiogenic effect in the tumor microenvironment of a murine orthotopic HCC model. The efficient delivery of VEGF siRNA by L4-LCP NPs that resulted in significant tumor regression indicates that phenyl galactoside could be a promising HCC-targeting ligand for therapeutic siRNA delivery to treat liver cancer.
Enzymatic procedure catalysed by lipase from Candida antarctica for the regioprotection-deprotection of glucosamine
Nicolosi, Giovanni,Spatafora, Carmela,Tringali, Corrado
, p. 2891 - 2897 (1999)
Both peracetyl α-glucosamine 3 and its β-epimer 4 undergo alcoholysis with butanol in THF, catalysed by lipase from Candida antarctica (Novozym 435) to afford the triester 6 and diester 9, respectively. Esterification of these compounds, using vinyl acetate in the presence of Novozym 435, gives the partial esters 10 and 11, bearing a deprotected hydroxyl function at C-4, ready for inversion of configuration to open a route in the preparation of galactosamine.
