Imaging active site chemistry and protonation states: NMR crystallography of the tryptophan synthase α-aminoacrylate intermediate was written by Holmes, Jacob B.;Liu, Viktoriia;Caulkins, Bethany G.;Hilario, Eduardo;Ghosh, Rittik K.;Drago, Victoria N.;Young, Robert P.;Romero, Jennifer A.;Gill, Adam D.;Bogie, Paul M.;Paulino, Joana;Wang, Xiaoling;Riviere, Gwladys;Bosken, Yuliana K.;Struppe, Jochem;Hassan, Alia;Guidoulianov, Jevgeni;Perrone, Barbara;Mentink-Vigier, Frederic;Chang, Chia-en A.;Long, Joanna R.;Hooley, Richard J.;Mueser, Timothy C.;Dunn, Michael F.;Mueller, Leonard J.. And the article was included in Proceedings of the National Academy of Sciences of the United States of America in 2022.Name: (4-Formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate The following contents are mentioned in the article:
NMR-assisted crystallog.-the integrated application of solid-state NMR, x-ray crystallog., and 1st-principles computational chem.-holds significant promise for mechanistic enzymol.: by providing at.-resolution characterization of stable intermediates in enzyme active sites, including H atom locations and tautomeric equilibrium, NMR crystallog. offers insight into both structure and chem. dynamics. This integrated approach is used to characterize the tryptophan synthase α-aminoacrylate intermediate, a defining species for pyridoxal-5′-phosphate-dependent enzymes that catalyze β-elimination and replacement reactions. For this intermediate, NMR-assisted crystallog. is able to identify the protonation states of the ionizable sites on the cofactor, substrate, and catalytic side chains as well as the location and orientation of crystallog. waters within the active site. Most notable is the H2O mol. immediately adjacent to the substrate β-C, which serves as a H bond donor to the ε-amino group of the acid-base catalytic residue βLys87. From this anal., a detailed 3-dimensional picture of structure and reactivity emerges, highlighting the fate of the
(4-Formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate (cas: 54-47-7) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Name: (4-Formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate