162088-88-2Relevant articles and documents
Escherichia coli LacZ β-galactosidase inhibition by monohydroxy acetylated glycopyranosides: Role of the acetyl groups
Brabcova, Jana,Carrasco-Lopez, Cesar,Bavaro, Teodora,Hermoso, Juan A.,Palomo, Jose M.
, p. 31 - 38 (2014)
Escherichia coli LacZ β-galactosidase is an extensively employed glycosidase for many different scientific purposes. Here, we describe how acetyl moieties protecting hydroxyl groups of the glycosides make these molecules better inhibitors to the enzyme activity. In particular, the presence of a unique hydroxyl group in the peracetylated glycosides still enhanced the inhibitory capacity of the molecule more. Molecular docking studies showed that the acetylation in the carbohydrate structure helps the substrate to accommodate into the active site. From a small biocatalytic synthesized library of different monohydroxy acetylated glycosides we can conclude that galactosidic structures are better for inhibition capacity. The best inhibitors were two monohydroxy lactal derivatives. The one with the OH free, in C-6 of the galactosidic part of the disaccharide, was a better inhibitor (Ki of 95 μM) than that with the OH free in C-3 in the glucosidic part of the molecule (Ki of 143 μM).
Propargyl-containing xylose and synthesis method thereof
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, (2020/07/28)
The invention discloses propargyl-containing xylose and a preparation method thereof. The method comprises the following steps: using D-xylose as a raw material, carrying out full acetyl protection onthe D-xylose, introducing p-nitrophenoxy into a first position of an obtained compound, and removing acetyl to obtain a compound A; introducing tert-butyl dimethyl into the position 2, the position 3or the position 4 of the obtained compound A to obtain a compound B, a compound C and a compound D, and separating the compound B, the compound C and the compound D; and respectively carrying out acetyl protection on hydroxyl groups of the compound B, the compound C and the compound D, then removing the tert-butyl dimethyl, and respectively introducing propargyl into the position 2, the position3 and the position 4 to obtain the propargyl-containing xylose. According to the method disclosed by the invention, the propargyl is selectively connected to xylose for the first time by using a method for carrying out occupying by using tert-butyl dimethyl (TBS), so that a platform is provided for subsequent connection of the xylose to protein or amino acid, and a foundation is laid for biological research in the future.
Regioselective monohydrolysis of per-O-acetylated-1-substituted-β-glucopyranosides catalyzed by immobilized lipases
Mendes, Adriano A.,Rodrigues, Dasciana S.,Filice, Marco,Fernandez-Lafuente, Roberto,Guisan, Jose M.,Palomo, Jose M.
, p. 10721 - 10727 (2008/12/23)
The regioselective monohydrolysis of different peracetylated-β-glucopyranosides in aqueous media using immobilized preparations of three different lipases-those from Aspergillus niger (ANL), Candida rugose (CRL) and Candida antarctica B (CAL-B)-has been studied. Three very different immobilization strategies-covalent attachment, anionic exchange and interfacial activation on a hydrophobic support-were employed for each lipase. The role of the immobilization strategy and the effect of the presence of different moieties in the anomeric position of the substrate on the hydrolytic activities, specificities and regioselectivities of the lipases were investigated. For example, the PEI-ANL preparation exhibited 800 times higher activity than the octyl-ANL in the hydrolysis of 2-acetamido-2-deoxy-1-(4-nitrophenyl)-3,4,6-tri-O-acetyl-β-d-glucopyranoside-producing 4-OH derivative in 18% yield-whereas the octyl-ANL was five times more active than the PEI-ANL in the hydrolysis of 1-(4-nitrophenyl)-2,3,4-tri-O-acetyl-β-d-xylopyranoside, producing 4-OH monohydroxy product in >99% yield. The octyl-CRL preparation hydrolyzed regioselectively 3,4,6-tri-O-acetyl-glucal in position 6 in 68% yield while the PEI-CRL produced the 3-OH product in 11% yield, although with moderate specificity. The CNBr-CAL-B hydrolyzed specifically and regioselectively the glucal producing the 3-OH product in >99% yield.
Lipase-catalysed preparation of acetates of 4-nitrophenyl β-D-xylopyranoside and their use in kinetic studies of acetyl migration
Mastihubova, Maria,Biely, Peter
, p. 1353 - 1360 (2007/10/03)
Di-O-acetates and mono-O-acetates of 4-nitrophenyl β-D-xylopyranoside were prepared by use of lipase PS-30. Polarity of organic solvents and reaction time affected the regioselectivity of the di-O-acetylation as well as the yields of monoacetates. The kin
A short synthesis of β-xylobiosides
Ziser, Lothar,Withers, Stephen G.
, p. 9 - 18 (2007/10/02)
Benzyl 2,3,2',3',4'-penta-O-acetyl-β-xylobioside, 2-nitrophenyl β-xylobioside, 4-nitrophenyl β-xylobioside, and 2-iodobenzyl 1-thio-β-xylobioside were synthesized via a short and highly selective route. β-D-Xylopyranosides were selectively 4-O-triethylsil
