Antivitamins B12: Synthesis and application as inhibitory ligand of the B12-tailoring enzyme CblC

Adams, 2002, PHENIX: Building new software for automated crystallographic structure determination, Acta Crystallographica, Section D: Biological Crystallography, 58, 1948, 10.1107/S0907444902016657 1999 Banerjee, 2009, The tinker, tailor, soldier in intracellular B12 trafficking, Current Opinion in Chemical Biology, 13, 484, 10.1016/j.cbpa.2009.07.007 Banerjee, 2021, Redox-linked coordination chemistry directs vitamin B-12 trafficking, Accounts of Chemical Research, 54, 2003, 10.1021/acs.accounts.1c00083 Banerjee, 2003, The many faces of vitamin B12: Catalysis by cobalamin-dependent enzymes, Annual Review of Biochemistry, 72, 209, 10.1146/annurev.biochem.72.121801.161828 Brenig, 2017, Alpha- and Beta-Diastereoisomers of Phenylcobalamin from cobalt-Arylation with Diphenyliodonium chloride, Chemistry--A European Journal, 23, 9726, 10.1002/chem.201701514 Chrominski, 2013, Reduction-free synthesis of stable acetylide cobalamins, Chemical Communications, 49, 11406, 10.1039/c3cc47210h Chrominski, 2014, Vitamin B12 derivatives for orthogonal functionalization, The Journal of Organic Chemistry, 79, 7532, 10.1021/jo501271g Davis, 2007, MolProbity: All-atom contacts and structure validation for proteins and nucleic acids, Nucleic Acids Research, 35(Web Server) Eschenmoser, 1988, Vitamin-B12 - experiments concerning the origin of its molecular-structure, Angewandte Chemie, International Edition, 27, 5, 10.1002/anie.198800051 Evans, 2013, How good are my data and what is the resolution?, Acta Cryst, D69, 1204 Fedosov, S. N. (2012) Physiological and molecular aspects of cobalamin transport. In J. R. Harris (Series Ed.), Subcellular biochemistry: Vol. 56. Water soluble vitamins (pp. 347-368): Springer. Fenn, 1989, Electrospray ionization for mass spectrometry of large biomolecules, Science, 246, 64, 10.1126/science.2675315 Froese, 2012, Structure of MMACHC reveals an arginine-rich pocket and a domain-swapped dimer for its B12 processing function, Biochemistry, 51, 5083, 10.1021/bi300150y Gherasim, 2013, Navigating the B12 road: Assimilation, delivery, and disorders of cobalamin, The Journal of Biological Chemistry, 288, 13186, 10.1074/jbc.R113.458810 Green, 2017, Vitamin B12 deficiency, Nature Reviews. Disease Primers, 3, 17040, 10.1038/nrdp.2017.40 Guzzo, 2016, Methylfolate trap promotes bacterial Thymineless death by sulfa drugs, PLoS Pathogens, 12, 10.1371/journal.ppat.1005949 Hannibal, 2009, Processing of alkylcobalamins in mammalian cells: A role for the MMACHC (cblC) gene product, Molecular Genetics and Metabolism, 97, 260, 10.1016/j.ymgme.2009.04.005 Hein, 2009, Copper(I)-catalyzed cycloaddition of organic azides and 1-iodoalkynes, Angewandte Chemie, International Edition, 48, 8018, 10.1002/anie.200903558 Hodgkin, 1956, Structure of vitamin-B12, Nature, 178, 64, 10.1038/178064a0 Kabsch, 2010, XDS, Acta Cryst, D66, 125 Kieninger, 2019, Zinc Substitution of Cobalt in Vitamin B12 : Zincobyric acid and Zincobalamin as Luminescent Structural B12-Mimics, Angewandte Chemie, International Edition, 58, 14568, 10.1002/anie.201908428 Kieninger, 2019, The Hydrogenobyric acid structure reveals the Corrin ligand as an Entatic state module empowering B12-cofactors for catalysis, Angewandte Chemie, International Edition, 58, 10756, 10.1002/anie.201904713 Kieninger, 2020, Replacement of the cobalt-center of vitamin B12 by nickel–Nibalamin and Nibyric acid prepared from metal-free B12-ligands hydrogenobalamin and hydrogenobyric acid, Angewandte Chemie, International Edition, 59, 20129, 10.1002/anie.202008407 Kim, 2008, Decyanation of vitamin B12 by a trafficking chaperone, Proceedings of the National Academy of Sciences of the United States of America, 105, 14551, 10.1073/pnas.0805989105 Kim, 2009, A human vitamin B12 trafficking protein uses glutathione transferase activity for processing Alkylcobalamins, The Journal of Biological Chemistry, 284, 33418, 10.1074/jbc.M109.057877 Konrat, 1998, New NMR structural and dynamical probes of organometallic B12 derivatives, 349 Koppenhagen, 1982, Metal-Free Corrinoids and Metal Insertion, 2, 105 Koutmos, 2011, Structural basis of multifunctionality in a vitamin B12-processing enzyme, The Journal of Biological Chemistry, 286, 9780, 10.1074/jbc.M111.261370 Kräutler, 2015, Antivitamins B12 - a structure- and reactivity-based concept, Chemistry - A European Journal, 21, 11280, 10.1002/chem.201502072 Kräutler, 2019, Biological organometallic chemistry of vitamin B12-derivatives, 399 Kräutler, 2020, Antivitamins B12 - Some Inaugural Milestones, Chemistry - A European Journal, 26, 15438, 10.1002/chem.202003788 1998 Leeper, 2012, Biosynthesis of vitamin B12, Vol. 25, 2, 10.1142/9789814397605_0017 Lerner-Ellis, 2006, Identification of the gene responsible for methylmalonic aciduria and homocystinuria, cblC type, Nature Genetics, 38, 93, 10.1038/ng1683 Li, 2017, Coordination chemistry controls the thiol oxidase activity of the B12-trafficking protein CblC, The Journal of Biological Chemistry, 292, 9733, 10.1074/jbc.M117.788554 Mascarenhas, 2020, The human B12 trafficking protein CblC processes nitrocobalamin, The Journal of Biological Chemistry, 295, 9630, 10.1074/jbc.RA120.014094 McCoy, 2007, Phaser crystallographic software, Journal of Applied Crystallography, 40, 658, 10.1107/S0021889807021206 Miller, 2016, Toward the design of Photoresponsive conditional antivitamins B12: A transient absorption study of an Arylcobalamin and an Alkynylcobalamin, Journal of the American Chemical Society, 138, 14250, 10.1021/jacs.6b05299 Moriarty, 2009, Electronic ligand builder and optimization workbench (eLBOW): A tool for ligand coordinate and restraint generation, Acta Crystallographica, Section D: Biological Crystallography, 65, 1074, 10.1107/S0907444909029436 Murshudov, 2011, REFMAC5 for the refinement of macromolecular crystal structures, Acta Crystallographica, Section D: Biological Crystallography, 67, 355, 10.1107/S0907444911001314 Mutti, 2013, 4-Ethylphenyl-cobalamin impairs tissue uptake of vitamin B12 and causes vitamin B12 deficiency in mice, PLoS One, 8, 10.1371/journal.pone.0075312 Otwinowski, 1997, Processing of X-ray diffraction data collected in oscillation mode, Methods in Enzymology, 276, 307, 10.1016/S0076-6879(97)76066-X Pettersen, 2004, UCSF chimera: A visualization system for exploratory research and analysis, Journal of Computational Chemistry, 25, 1605, 10.1002/jcc.20084 Potterton, 2003, A graphical user interface to theCCP4 program suite, Acta Crystallographica, Section D: Biological Crystallography, 59, 1131, 10.1107/S0907444903008126 Ruetz, 2013, Radical synthesis opens access to organometallic aryl-Cobaltcorrins - 4-Ethylphenyl-cobalamin, a potential “antivitamin B12”, Angewandte Chemie, International Edition, 52, 2606, 10.1002/anie.201209651 Ruetz, 2013, Phenylethynylcobalamin: A light-stable and Thermolysis-resistant organometallic vitamin B12 derivative prepared by radical synthesis, Angewandte Chemie, International Edition, 52, 11406, 10.1002/anie.201305206 Ruetz, 2017, Antivitamin B12 inhibition of the human B12-processing enzyme CblC: Crystal structure of an inactive ternary complex with glutathione as the Cosubstrate, Angewandte Chemie, International Edition, 56, 7387, 10.1002/anie.201701583 Schrödinger., 2015 Schüttelkopf, 2004, PRODRG: A tool for high-throughput crystallography of protein–ligand complexes, Acta Crystallographica, Section D: Biological Crystallography, 60, 1355, 10.1107/S0907444904011679 Summers, 1986, Complete proton and carbon-13 assignments of coenzyme B12 through the use of new two-dimensional NMR experiments, Journal of the American Chemical Society, 108, 4285, 10.1021/ja00275a008 Widner, 2021, Synthesis, spectral characterization and crystal structure of Chloro-Rhodibalamin – A synthesis platform for rhodium analogues of vitamin B12 and for Rh-based antivitamins B12, Synthesis, 53, 332, 10.1055/s-0040-1707288 Widner, 2016, Total synthesis, structure, and biological activity of Adenosylrhodibalamin, the non-natural rhodium homologue of coenzyme B12, Angewandte Chemie, International Edition, 55, 11281, 10.1002/anie.201603738