title: A concise synthesis of beta-asparaginyladenylate.
abstract: Stable analogues of acyladenylate intermediates, such as N-acylphosphoramidates, are useful probes of tRNA aminoacylation and enzyme mechanism, and have potential application as enzyme inhibitors. We now report a concise, "one-pot" synthesis of beta-asparaginyladenylate using a novel coupling protocol that yields the target N-acylphosphoramidate in three reactions from readily available precursors. This simple synthetic procedure may represent a general approach for the preparation of functionalized N-acylphosphoramidates from amides that do not undergo coupling under the conditions of existing literature protocols.
authors.affiliation: Department of Chemistry, University of Florida, Gainesville 32611, USA.
authors.forename: Yun
authors.initials: Y
authors.lastname: Ding
authors.forename: Jianqiang
authors.initials: J
authors.lastname: Wang
authors.forename: Sheldon M
authors.initials: SM
authors.lastname: Schuster
authors.forename: Nigel G J
authors.initials: NG
authors.lastname: Richards
mesh_terms: D000577:Amides / Q000737:chemistry*; D001216:Asparagine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D002853:Chromatography, Liquid; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000138:chemical synthesis*
chemical_list: D000577:Amides; D010756:Phosphoric Acids; D001216:Asparagine