Enzymatically cleavable traceless biotin tags for protein PEGylation and purification.
Chemical communications (Cambridge, England)
2018; 54 (15): 1913?16
Newly characterized interaction stabilizes DNA structure: oligoethylene glycols stabilize G-quadruplexes CH-p interactions.
Nucleic acids research
Here we report an example of a protein-PEG conjugate with a biotin tag cleavable by lipase-catalyzed hydrolysis. Very mild cleavage conditions, heterogeneous, easily separable catalysts, and traceless design make this method attractive for the preparation and purification of PEGylated proteins.
View details for DOI 10.1039/c7cc05814d
View details for PubMedID 29393938
Multigram chromatography-free synthesis of octa(ethylene glycol) p-toluenesulfonate
ORGANIC CHEMISTRY FRONTIERS
2016; 3 (11): 1524-1534
Chromatography-free synthesis of monodisperse oligo(ethylene glycol) mono-p-toluenesulfonates and quantitative analysis of oligomer purity
2016; 7 (13): 2389-2394
Synthesis of novel chiral TBBt derivatives with hydroxyl moiety. Studies on inhibition of human protein kinase CK2 alpha and cytotoxicity properties
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
2014; 84: 364-374
Oligoethylene glycols are used as crowding agents in experiments that aim to understand the effects of intracellular environments on DNAs. Moreover, DNAs with covalently attached oligoethylene glycols are used as cargo carriers for drug delivery systems. To investigate how oligoethylene glycols interact with DNAs, we incorporated deoxythymidine modified with oligoethylene glycols of different lengths, such as tetraethylene glycol (TEG), into DNAs that form antiparallel G-quadruplex or hairpin structures such that the modified residues were incorporated into loop regions. Thermodynamic analysis showed that because of enthalpic differences, the modified G-quadruplexes were stable and the hairpin structures were slightly unstable relative to unmodified DNA. The stability of G-quadruplexes increased with increasing length of the ethylene oxides and the number of deoxythymidines modified with ethylene glycols in the G-quadruplex. Nuclear magnetic resonance analyses and molecular dynamics calculations suggest that TEG interacts with bases in the G-quartet and loop via CH-? and lone pair-? interactions, although it was previously assumed that oligoethylene glycols do not directly interact with DNAs. The results suggest that numerous cellular co-solutes likely affect DNA function through these CH-? and lone pair-? interactions.
View details for DOI 10.1093/nar/gkx299
View details for PubMedID 28453855
View details for PubMedCentralID PMC5499538
Synthesis of new optically pure tetrabromobenzotriazole derivatives via lipase-catalyzed transesterification
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC
2013; 87: 44-50
The efficient method for the synthesis of novel 4,5,6,7-tetrabromo-1H-benzotriazole (TBBt) derivatives bearing a single stereogenic center has been developed. New compounds with a variety of substituents at the meta- and para-position of the phenyl ring are reported. All of the presented compounds were obtained using classical synthetic methods, such as bromination of benzotriazole, and its subsequent alkylation by monotosylated arylpropane-1,3-diols, which in turn have been synthesized through reduction of the corresponding prochiral ?-keto esters, and the selective monotosylation of the primary hydroxyl group. The influence of the new and previously reported N-hydroxyalkyl TBBt derivatives on the activity of human protein kinase CK2? catalytic subunit was examined. The most active were derivatives with N-hydroxyalkyl substituents (IC50 in 0.80-7.35 ?M range). A binding mode of (R)-1-(4,5,6,7-tetrabromo-2H-benzotriazol-2-yl)butan-3-ol 7b to hCK2? has been proposed based on in silico docking studies. Additionally, MTT-based cytotoxicity tests demonstrated high activities of novel 1-aryl-3-TBBt-propan-1-ol and 3-TBBt-propan-1,2-diol derivatives against human peripheral blood T lymphoblast (CCRF-CEM), and moderate anti-tumor activities against human breast adenocarcinoma (MCF7) cell lines.
View details for DOI 10.1016/j.ejmech.2014.07.019
View details for Web of Science ID 000341464500033
View details for PubMedID 25036794