One-flask synthesis of cyclic diguanosine monophosphate (c-di-GMP)

Current Protocols in Nucleic Acid Chemistry

Volumn 1, Issue SUPPL. 48, 2012, Pages

  Gaffney, Barbara L ^a   Jones, Roger A ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

Bacterial signaling; C di GMP; Chemical synthesis

Indexed keywords

CYCLIC DIGUANOSINE MONOPHOSPHATE; CYCLIC GMP; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL VIRULENCE; BIOFILM; CHEMICAL MODIFICATION; CYCLIZATION; DEPROTECTION REACTION; DETRITYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; NUCLEIC ACID SYNTHESIS; ONE FLASK SYNTHESIS; PRIORITY JOURNAL; RIBOSWITCH; SIGNAL TRANSDUCTION;

BACTERIA (MICROORGANISMS);

EID: 84863756018     PISSN: 19349270     EISSN: 19349289     Source Type: Journal    
DOI: 10.1002/0471142700.nc1408s48     Document Type: Article

References (20)

1. Amiot, N., Heintz, K., and Giese, B. 2006. New approach for the synthesis of c-di-GMP and its analogues. Synthesis 24:4230-4236.
2. Cotter, P.A. and Stibitz, S. 2007. c-di-GMPmediated regulation of virulence and biofilm formation. Curr. Opin. Microbiol. 10:17-23.
3. Gaffney, B.L., Veliath, E., Zhao, J., and Jones, R.A. 2010. One-flask syntheses of c-di-GMP and the [Rp, Rp] and [Rp, Sp] thiophosphate analogues. Org. Lett. 12:3269-3271.
4. Hayakawa, Y., Nagata, R., Hirata, A., Hyodo, M., and Kawai, R. 2003. A facile synthesis of cyclic bis(3'-5' )diguanylic acid. Tetrahedron 59:6465-6471.
5. Hengge, R. 2009. Principles of c-di-GMP signalling in bacteria. Nat. Rev. Microbiol. 7:263-273.
6. Hyodo, M. and Hayakawa, Y. 2004. An improved method for synthesizing cyclic bis (3' -5' )diguanlic acid (c-di-GMP). Bull. Chem. Soc. Jpn. 77:2089-2093.
7. Hyodo, M., Sato, Y., and Hayakawa, Y. 2006. Synthesis of cyclic bis(3' -5' )diguanylic acid (c-di-GMP) analogs. Tetrahedron 62:3089-3094.
8. Kiburu, I., Shurer, A., Yan, L., and Sintim, H.O. 2008. A simple solid-phase synthesis of the ubiquitous bacterial signaling molecule, c-di-GMP and analogues, Mol. BioSyst. 4:518-520.
9. Ko, J., Ryu, K.-S., Kim, H., Shin, J.-S., Lee, J.-O., Cheong, C., and Choi, B.-S. 2010. Structure of PP4397 reveals the molecular basis for different c-di-GMP binding modes by Pilz domain proteins. J. Mol. Biol. 398:97-110.
10. Kulshina, N., Baird, N.J., and Ferré-D'Amaré, A.R. 2009. Recognition of the bacterial second messenger cyclic diguanylate by its cognate riboswitch, Nat. Struct.Mol. Biol. 16:1212-1217.
11. Lee, E.R., Baker, J.L., Weinberg, Z., Sudarsan, N., and Breaker, R.R. 2010. An allosteric selfsplicing ribozyme triggered by a bacterial second messenger Science 329:845-848.
12. Romling, U. and Amikam, D. 2006. Cyclic di-GMP as a second messenger. Curr. Opin. Microbiol. 9:218-228.
13. Ross, P., Mayer, R., Weinhouse, H., Amikam, D., Huggirat, Y., Benziman, M., de Vroom, E., Fidder, A., Paus, P.d., Sliedregt, L.A.J.M., van der Marel, G.A., and van Boom, J.H. 1990. The cyclic diguanylic acid regulatory system of cellulose synthesis in Acetobacter xylinum. J. Biol. Chem. 265:18933-18943.
14. Schirmer, T. and Jenal, U. 2009. Structural and mechanistic determinants of c-di-GMP signalling. Nat. Rev. Micro. 7:724-735.
15. Smith, K.D., Lipchock, S.V., Ames, T.D., Wang, J., Breaker, R R., and Strobel, S.A. 2009. Structural basis of ligand binding by a c-di-GMP riboswitch. Nat. Struct. Mol. Biol. 16:1218-1223.
16. Smith, K.D., Shanahan, C.A., Moore, E.L., Simon, A.C., and Strobel, S.A. 2011. Structural basis of differential ligand recognition by two classes of bis-(3' -5' )-cyclic dimeric guanosine monophosphate-binding riboswitches. Proc. Natl. Acad. Sci. U.S.A. 108:7757-7762.
17. Sudarsan, N., Lee, E.R., Weinberg, Z., Moy, R.H., Kim, J.N., Link, K.H., and Breaker, R.R. 2008. Riboswitches in eubacteria sense the second messenger cyclic di-GMP. Science 321:411-413.
18. Tamayo, R., Pratt, J.T., and Camilli, A. 2007. Roles of cyclic diguanylate in the regulation of bacterial pathogenesis, Ann. Rev. Microbiol. 61:131-148.
19. Yan, H. and Aguilar, A.L. 2007. Synthesis of 3' ,5' -cyclic diguanylic acid (cdiGMP) using 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl as a protecting group for 2' -hydroxy functions of ribonucleosides. Nucleosides Nucleotides Nucleic Acids 26:189-204.
20. Zhang, Z., Gaffney, B.L., and Jones, R.A. 2004. c-di-GMP displays a monovalent metal iondependent polymorphism, J. Am. Chem. Soc. 126:16700-16701.