A concise synthesis of beta-asparaginyladenylate.
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.
Ding
Yun
Y
Department of Chemistry, University of Florida, Gainesville 32611, USA.
Wang
Jianqiang
J
Schuster
Sheldon M
SM
Richards
Nigel G J
NG
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*
D000577:Amides; D010756:Phosphoric Acids; D001216:Asparagine