14227-66-8Relevant articles and documents
Synthesis and evaluation of a series of 6-chloro-4-methylumbelliferyl glycosides as fluorogenic reagents for screening metagenomic libraries for glycosidase activity
Chen, Hong-Ming,Armstrong, Zachary,Hallam, Steven J.,Withers, Stephen G.
, p. 33 - 39 (2016)
Screening of large enzyme libraries such as those derived from metagenomic sources requires sensitive substrates. Fluorogenic glycosides typically offer the best sensitivity but typically must be used in a stopped format to generate good signal. Use of fluorescent phenols of pKa 7, such as halogenated coumarins, allows direct screening at neutral pH. The synthesis and characterisation of a set of nine different glycosides of 6-chloro-4-methylumbelliferone are described. The use of these substrates in a pooled format for screening of expressed metagenomic libraries yielded a "hit rate" of 1 in 60. Hits were then readily deconvoluted with the individual substrates in a single plate to identify specific activities within each clone. The use of such a collection of substrates greatly accelerates the screening process.
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Brundish,Baddiley
, p. 308,312 (1968)
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Design and synthesis of hydrolytically stable multivalent ligands bearing thiodigalactoside analogues for peanut lectin and human galectin-3 binding
Cagnoni, Alejandro J.,Kovensky, José,Uhrig, María Laura
, p. 6456 - 6467 (2014)
Herein, we describe the design and synthesis of a novel family of hydrolytically stable glycoclusters bearing thiodigalactoside (TDG) analogues as recognition elements of β-galactoside binding lectins. The TDG analogue was synthesized by thioglycosylation of a 6-S-acetyl-α-d-glucosyl bromide with the isothiouronium salt of 2,3,4,6-tetra-O-acetyl-β-d-galactose. Further propargylation of the TDG analogue allowed the coupling to azido-functionalized oligosaccharide scaffolds through copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) under microwave activation. The final mono-, di-, and tetravalent ligands were resistant to enzymatic hydrolisis by Escherichia coli β-galactosidase. Binding affinities to peanut agglutinin and human galectin-3 were measured by isothermal titration calorimetry which showed Ka constants in the micromolar range as well as a multivalent effect. Monovalent ligand exhibited a binding affinity higher than that of thiodigalactoside. Docking studies performed with a model ligand on both β-galactoside binding lectins showed additional interactions between the triazole ring and lectin amino acid residues, suggesting a positive effect of this aromatic residue on the biological activity.
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Barczai-Martos,Koeroesy
, p. 369 (1950)
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Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents
Li, Xiao-San,Chen, Tang-Ji,Xu, Zhi-Peng,Long, Juan,He, Miao-Ying,Zhan, He-Hui,Zhuang, Hai-Cai,Wang, Qi-Lin,Liu, Li,Yang, Xue-Mei,Tang, Jin-Shan
, (2021/12/30)
In order to study the structure–activity relationship (SAR) of C21-steroidal glycosides toward human cancer cell lines and explore more potential anticancer agents, a series of 3β-O-neoglycosides of caudatin and its analogues were synthesized. The results revealed that most of peracetylated 3β-O-monoglycosides demonstrated moderate to significant antiproliferative activities against four human cancer cell lines (MCF-7, HCT-116, HeLa, and HepG2). Among them, 3β-O-(2,3,4-tri-O-acetyl-β-L-glucopyranosyl)-caudatin (2k) exhibited the highest antiproliferative activity aganist HepG2 cells with an IC50 value of 3.11 μM. Mechanical studies showed that compound 2k induced both apoptosis and cell cycle arrest at S phase in a dose dependent manner. Overall, these present findings suggested that glycosylation is a promising scaffold to improve anticancer activity for naturally occurring C21-steroidal aglycones, and compound 2k represents a potential anticancer agent deserved further investigation.
Halogenation and anomerization of glycopyranoside by TESH/bromine and BHQ/bromine
Xu, Lai,Luo, Chin-Hung,Chen, Chien-Sheng
, p. 315 - 321 (2020/07/13)
Treatment of peracetylated glycosides and β-isopropyl glycosides with halogen in the presence of TESH and BHQ has been found to result in the halogenation and the anomerization, respectively. Peracetylatedglycosides treaded with I2/TESH or Br2/TESH leading tothe formation of corresponding glycosyl halides, and b-isopropyl glycosidesreacted with Br2/BHQ resulting in the formation of a-glycosides. The anomerizationof glycosidic bond was considered to be catalyzed by in situ formation of hydrogenbromide from the mixing of Br2/BHQ.
Compound, nitric oxide donor prodrug compound as well as preparation method and application of compound and nitric oxide donor prodrug compound
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, (2021/03/11)
The invention relates to the technical field of biological medicines, in particular to a compound, a nitric oxide donor prodrug compound as well as a preparation method and application of the compoundand the nitric oxide donor prodrug compound. The compound has a structure as shown in a formula I-1, is used for preparing the nitric oxide donor prodrug compound with a structure shown in a formulaI. The preparation method of the compound comprises the following steps: step c), condensing a compound as shown in a formula I-2 with pyrrolidinyl diazonium glycol sodium salt to prepare the compoundas shown in a formula I-1. The preparation method of the nitric oxide donor prodrug compound comprises the following steps: step d), deacetylating the compound of formula I-1 to prepare the compoundof formula I. The nitric oxide donor prodrug compound can controllably release nitric oxide under catalysis of endocellulase, and can controllably release nitric oxide under orthogonal catalysis of endocellulase Cel5A-h38 natural organisms. Therefore, a characteristic that nitric oxide can be controllably released as required is utilized for preparing a medicine capable of controllably releasing nitric oxide.
