21317-51-1Relevant articles and documents
Quantitative Prediction of Yield in Transglycosylation Reaction Catalyzed by Nucleoside Phosphorylases
Alexeev, Cyril S.,Kulikova, Irina V.,Gavryushov, Sergei,Tararov, Vitali I.,Mikhailov, Sergey N.
, p. 3090 - 3096 (2018)
Phosphorolytic transglycosylation catalyzed by nucleoside phosphorylases is an important biotechnological process. The reaction is reversible, and the yield of the target nucleoside depends on its concentration at the equilibrium state. We have shown that initial concentrations of the starting compounds and the phosphorolysis equilibrium constants of starting and final glycosides determine concentrations of all the components at the equilibrium state. Based on that, we developed a novel quantitative approach for the prediction of yields in transglycosylation reactions. This method simplifies the choice of reagent concentrations and their ratios for the maximization of the target nucleoside yield. It is advantageous over widely applied blind and cumbersome trial-and-error approach and can reduce the required chemical and energy resources. The described algorithm could also be applied for other equilibrium transfer reactions. (Figure presented.).
Synthesis of a C-phosphonate mimic of maltose-1-phosphate and inhibition studies on Mycobacterium tuberculosis GlgE
Veleti, Sri Kumar,Lindenberger, Jared J.,Ronning, Donald R.,Sucheck, Steven J.
, p. 1404 - 1411 (2014/03/21)
The emergence of extensively drug-resistant tuberculosis (XDR-TB) necessitates the need to identify new anti-tuberculosis drug targets as well as to better understand essential biosynthetic pathways. GlgE is a Mycobacterium tuberculosis (Mtb) encoded maltosyltransferase involved in α-glucan biosynthesis. Deletion of GlgE in Mtb results in the accumulation of M1P within cells leading to rapid death of the organism. To inhibit GlgE a maltose-C-phosphonate (MCP) 13 was designed to act as an isosteric non-hydrolysable mimic of M1P. MCP 13, the only known inhibitor of Mtb GlgE, was successfully synthesized using a Wittig olefination as a key step in transforming maltose to the desired product. MCP 13 inhibited Mtb GlgE with an IC50 = 230 ± 24 μM determined using a coupled enzyme assay which measures orthophosphate release. The requirement of M1P for the assay necessitated the development of an expedited synthetic route to M1P from an intermediate used in the MCP 13 synthesis. In conclusion, we designed a substrate analogue of M1P that is the first to exhibit Mtb GlgE inhibition.
Nucleotidylation of unsaturated carbasugar in validamycin biosynthesis
Yang, Jongtae,Xu, Hui,Zhang, Yirong,Bai, Linquan,Deng, Zixin,Mahmud, Taifo
experimental part, p. 438 - 449 (2011/03/17)
Validamycin A is a member of microbial-derived C7N-aminocyclitol family of natural products that is widely used as crop protectant and the precursor of the antidiabetic drug voglibose. Its biosynthetic gene clusters have been identified in seve
