1136-52-3Relevant articles and documents
Synthesis of hydrolysis-resistant pyridoxal 5′-phosphate analogs and their biochemical and X-ray crystallographic characterization with the pyridoxal phosphatase chronophin
Knobloch, Gunnar,Jabari, Nauras,Stadlbauer, Sven,Schindelin, Hermann,K?hn, Maja,Gohla, Antje
, p. 2819 - 2827 (2015)
A set of phosphonic acid derivatives (1-4) of pyridoxal 5′-phosphate (PLP) was synthesized and characterized biochemically using purified murine pyridoxal phosphatase (PDXP), also known as chronophin. The most promising compound 1 displayed primarily competitive PDXP inhibitory activity with an IC50 value of 79 μM, which was in the range of the Km of the physiological substrate PLP. We also report the X-ray crystal structure of PDXP bound to compound 3, which we solved to 2.75 ? resolution (PDB code 5AES). The co-crystal structure proves that compound 3 binds in the same orientation as PLP, and confirms the mode of inhibition to be competitive. Thus, we identify compound 1 as a PDXP phosphatase inhibitor. Our results suggest a strategy to design new, potent and selective PDXP inhibitors, which may be useful to increase the sensitivity of tumor cells to treatment with cytotoxic agents.
Synthesis, molecular docking and spectroscopic studies of pyridoxine carbamates as metal chelator
Pal, Tiyas,Patil, Pooja,Sharma, Abha
, (2021)
Herein, we have reported synthesis, characterization, molecular docking and metal chelating potential of various pyridoxine carbamates for biometals (copper, zinc and iron) via spectroscopic methods. All the derivatives showed metal chelation ability and 4g was found the most potent metal chelator, having a binding stoichiometry of 1:1 with Cu+2 ion. Interactions of metal with ligand 4g was studied and the participation of both carbamate and free –OH group in complex formation was confirmed. All the synthesized compounds showed druglikeness properties, passing the lipinki's Rule of five. According to Pass study 4a, 4b, 4d and 4h to show significant nootropic activity (Pa > 0.60) in comparison to donepezil. Fluorescence quenching study and analysis with BSA with 4g showed static quenching mechanism. Molecular docking showed probable site of binding with least binding energy of ?5.9 kcal mol?1. The compound 4g also showed binding with acetylcholinesterase in UV–Vis spectrum. The study concludes that pyridoxine-carbamates are biometal chelator, possess other properties also like drug likeness, binding with BSA and acetylcholinetersae.
Chemical synthesis of 5’-β-glycoconjugates of vitamin B6
Bachmann, Thomas,Schnurr, Christian,Zainer, Laura,Rychlik, Michael
, (2020)
Various 5’-β-saccharides of pyridoxine, namely the mannoside, galactoside, arabinoside, maltoside, cellobioside and glucuronide, were synthesized chemically according to KOENIGS-KNORR conditions using α4,3-O-isopropylidene pyridoxine and the respective acetobromo glycosyl donors with AgOTf (3.0 eq.) and NIS (3.0 eq.) as promoters at 0 °C. Furthermore, 5’-β-[13C6]-labeled pyridoxine glucoside (PNG) was prepared starting from [13C6]-glucose and pyridoxine. Additionally, two strategies were examined for the synthesis of 5’-β-pyridoxal glucoside (PLG).
Chemical glucosylation of pyridoxine
Bachmann, Thomas,Rychlik, Michael
, (2020/02/13)
The chemical synthesis of pyridoxine-5′-β-D-glucoside (5′-β-PNG) was investigated using various glucoside donors and promoters. Hereby, the combination of α4,3-O-isopropylidene pyridoxine, glucose vested with different leaving and protecting groups and the application of stoichiometric amounts of different promoters was examined with regards to the preparation of the twofold protected PNG. Best results were obtained with 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl fluoride and boron trifluoride etherate (2.0 eq.) as promoter at 0 °C (59%). The deprotection was accomplished stepwise with potassium/sodium hydroxide in acetonitrile/water followed by acid hydrolysis with formic acid resulting in the chemical synthesis of 5′-β-PNG.