title: Synthesis and characterization of C8 analogs of c-di-GMP.
abstract: We have synthesized five analogs of c-di-GMP with different substituents at the guanine C8 position, to study their effects on the metal-dependent polymorphism we had previously demonstrated for the parent compound. Of these, only the K(+) salt of c-di-Br-GMP, 2, forms higher order complexes, predominantly two different syn octamolecular ones. Its Na(+) salt, as well as both the K(+) and Na(+) salts of c-di-thio-GMP, 3, c-di-methylthio-GMP, 4, c-di-phenyl-GMP, 5, and c-di-acetylphenyl-GMP, 6, all form primarily a syn bimolecular structure.
authors: Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.
authors: Elizabeth
authors: E
authors: Veliath
authors: Seho
authors: S
authors: Kim
authors: Barbara L
authors: BL
authors: Gaffney
authors: Roger A
authors: RA
authors: Jones
mesh_terms: D001966:Bromine / Q000737:chemistry; D006152:Cyclic GMP / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D011188:Potassium / Q000737:chemistry; D012492:Salts / Q000138:chemical synthesis / Q000737:chemistry*; D012964:Sodium / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D012492:Salts; D013438:Sulfhydryl Compounds; C062025:bis(3',5')-cyclic diguanylic acid; D012964:Sodium; D006152:Cyclic GMP; D011188:Potassium; D001966:Bromine