Abstract
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 1H and 31P 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 [SP] sulfurs specifically stabilizes anti complexes and/or destabilizes syn complexes, while the presence of two [SP] sulfurs promotes extensive aggregation.
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