title: Synthesis of a hydrolytically stable, fluorescent-labeled ATP analog as a tool for probing adenylyl cyclases.
abstract: (2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3-hydroxy-4-[2-(methylamino)benzamido]tetrahydrofuran-2-yl-methoxy[(hydroxy)phosphoryloxy][(hydroxy)phosphoryl]dichloromethylphosphonic acid was synthesized as a chemically and metabolically stable analog of ATP substituted with a fluorescent methylanthranoyl (MANT) residue. The compound is intended for studying the binding site and function of adenylyl cyclases (ACs), which was exemplified by studying its interaction with Bacillus anthracis edema factor (EF) AC exotoxin.
authors.affiliation: Institute of Pharmacy, Ernst-Moritz-Arndt-University, Friedrich-Ludwig-Jahn-Strasse 17, D-17487 Greifswald, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Emmrich
authors.forename: Ali
authors.initials: A
authors.lastname: El-Tayeb
authors.forename: Hesham
authors.initials: H
authors.lastname: Taha
authors.forename: Roland
authors.initials: R
authors.lastname: Seifert
authors.forename: Christa E
authors.initials: CE
authors.lastname: Müller
authors.forename: Andreas
authors.initials: A
authors.lastname: Link
mesh_terms: D000255:Adenosine Triphosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000262:Adenylyl Cyclases / Q000737:chemistry* / Q000378:metabolism; D001408:Bacillus anthracis / Q000201:enzymology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005456:Fluorescent Dyes / Q000737:chemistry*; D006860:Hydrogen Bonding; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D004791:Enzyme Inhibitors; D005456:Fluorescent Dyes; D009943:Organophosphorus Compounds; C025303:(dichloromethyl)phosphonic acid; D000255:Adenosine Triphosphate; D000262:Adenylyl Cyclases