Trypanosoma cruzi trans-sialidase alternative substrates: Study of the effect of substitution in C-6 in benzyl β-lactoside

Add time:09/02/2019    Source:sciencedirect.com

Trypanosoma cruzi trans-sialidase (TcTS) is a cell surface protein that participates in the adhesion and invasion mechanisms of the parasite into the host cells, making it an attractive target for inhibitors design. In order to contribute to the knowledge of the interaction between TcTS and their acceptor substrates, we designed and synthesized a library of 20 benzyl lactosides substituted in C-6 of the glucose residue with a series of 1,2,3-triazole derivatives containing different aromatic substituents in the C-4 position. The library was prepared by alkyne-azide cycloaddition reaction catalyzed by Cu(I) (“click chemistry”) between a benzyl β-lactoside functionalized with an azide group in the C-6 position and a series of 2-propargyl phenyl ethers. Herein we analyzed the chromatographic behavior on high performance anion exchange chromatography (HPAEC) of the triazoyl-lactose derivatives and their activity as acceptors of TcTS and inhibitors of the sialylation of N-acetyllactosamine. The triazoyl derivatives were obtained with excellent yields and all of them behaved as moderate alternative substrates. The presence of bulky hydrophobic substituents dramatically increased the retention times in HPAEC but did not affect significantly their acceptor properties toward TcTS.

We also recommend Trading Suppliers and Manufacturers of Benzene,1-[(trans,trans)-4'-ethyl[1,1'-bicyclohexyl]-4-yl]-4-fluoro- (Related Reference) (cas 114175-93-8). Pls Click Website Link as below: cas 114175-93-8 suppliers

Prev:Tautomeric preferences of the cis and trans isomers of axitinib
Next:Fatty acids attached to all-trans-astaxanthin alter its cis–trans equilibrium, and consequently its stability, upon light-accelerated autoxidation)