title: Total synthesis of the hypermodified RNA bases wybutosine and hydroxywybutosine and their quantification together with other modified RNA bases in plant materials.
abstract: We report an efficient synthesis of the hypermodified natural tRNA modifications wybutosine (yW) and hydroxywybutosine (OHyW). We also describe the preparation of isotopically labeled analogues for precise quantification of yW and OHyW in different tissues including plant materials. The synthesis involved the formation of the unusual tricyclic ring structure of the bases by using a catalytic, intramolecular hydroamination reaction. The basis for the synthesis is also a stereoselective coupling reaction that allows the introduction of the fully substituted side chains to the tricyclic core structure. The isotopologues of yW and OHyW, together with other isotopically labeled tRNA modifications, were ultimately used in LC-MS quantification experiments to investigate the role of the modified bases in the translational process. Quantification was performed in the plant species Arabidopsis thaliana.
authors: Center for Integrated Protein Science (CIPS) at the Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, 81377 München, Germany.
authors: Antje
authors: A
authors: Hienzsch
authors: Christian
authors: C
authors: Deiml
authors: Veronika
authors: V
authors: Reiter
authors: Thomas
authors: T
authors: Carell
mesh_terms: D000818:Animals; D017360:Arabidopsis / Q000737:chemistry*; D002853:Chromatography, Liquid; D006151:Guanosine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D007553:Isotope Labeling; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009705:Nucleosides / Q000737:chemistry*; D012343:RNA, Transfer / Q000737:chemistry*; D013552:Swine
chemical_list: D009705:Nucleosides; C467591:wybutosine; D006151:Guanosine; D012343:RNA, Transfer