Journal
MOLECULES
Volume 17, Issue 11, Pages 13376-13389Publisher
MDPI
DOI: 10.3390/molecules171113376
Keywords
c-di-GMP; endo-S-c-di-GMP; polymorphism; G-quadruplex; analogues; DOSY; Vc2 RNA; fluorescence; aptamer
Funding
- National Science Foundation [CHE0746446]
- Camille Dreyfus Foundation
- American Heart Association [11PRE7890040]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0746446] Funding Source: National Science Foundation
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C-di-GMP, a cyclic guanine dinucleotide, has been shown to regulate biofilm formation as well as virulence gene expression in a variety of bacteria. Analogues of c-di-GMP have the potential to be used as chemical probes to study c-di-GMP signaling and could even become drug leads for the development of anti-biofilm compounds. Herein we report the synthesis and biophysical studies of a series of c-di-GMP analogues, which have both phosphate and sugar moieties simultaneously modified (called endo-S-c-di-GMP analogues). We used computational methods to predict the relative orientation of the guanine nucleobases in c-di-GMP and analogues. DOSY NMR of the endo-S-c-di-GMP series showed that the polymorphism of c-di-GMP can be tuned with conservative modifications to the phosphate and sugar moieties (conformational steering). Binding studies with Vc2 RNA (a class I c-di-GMP riboswitch) revealed that conservative modifications to the phosphate and 2'-positions of c-di-GMP dramatically affected binding to class I riboswitch.
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