title: Synthesis of c-di-GMP analogs with thiourea, urea, carbodiimide, and guanidinium linkages.
abstract: The first syntheses of neutral thiourea, urea, and carbodiimide analogs, along with two guanidinium analogs, of the bacterial signaling molecule cyclic diguanosine monophosphate (c-di-GMP) are reported. The key intermediate, obtained in nine steps, is a 3'-amino-5'-azido-3',5'-dideoxy derivative. The 5'-azide serves as a masked amine from which the amine is obtained by Staudinger reduction, while the 3'-amine is converted to an isothiocyanate that, while stable to chromatography, and Staudinger conditions, nevertheless reacts well with the 5'-amine.
authors: Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey , 610 Taylor Road, Piscataway, New Jersey 08854, United States.
authors: Barbara L
authors: BL
authors: Gaffney
authors: Roger A
authors: RA
authors: Jones
mesh_terms: D002234:Carbodiimides / Q000737:chemistry*; D006152:Cyclic GMP / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D019791:Guanidine / Q000737:chemistry*; D009690:Nucleic Acid Conformation; D014508:Urea / Q000031:analogs & derivatives / Q000737:chemistry*
chemical_list: D002234:Carbodiimides; C062025:bis(3',5')-cyclic diguanylic acid; D014508:Urea; D006152:Cyclic GMP; D019791:Guanidine