Thiophosphate analogs of c-di-GMP: impact on polymorphism.
Seven phosphorothioate analogs of c-di-GMP (all diastereomers of mono-, di-, and trithiophosphates) were prepared to assess the impact of the thioate substitutions on c-di-GMP polymorphism using 1D (1)H and (31)P NMR, along with 2D NOESY and DOSY, for both the Na(+) and K(+) salts. The K(+) salts display more extensive higher order complex formation than the Na(+) salts, resulting primarily in octamolecular complexes with K(+), but tetramolecular complexes with Na(+). Further, the presence of one or two [S(P)] sulfurs specifically stabilizes anti complexes and/or destabilizes syn complexes, while the presence of two [S(P)] sulfurs promotes extensive aggregation.
Zhao
Jianwei
J
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey, USA.
Veliath
Elizabeth
E
Kim
Seho
S
Gaffney
Barbara L
BL
Jones
Roger A
RA
D006152:Cyclic GMP / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010710:Phosphates / Q000737:chemistry*; D011188:Potassium / Q000737:chemistry; D012492:Salts / Q000737:chemistry; D012964:Sodium / Q000737:chemistry
D010710:Phosphates; D012492:Salts; C062025:bis(3',5')-cyclic diguanylic acid; D012964:Sodium; D006152:Cyclic GMP; D011188:Potassium; C035638:thiophosphoric acid