Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2006(24): 4230-4236
DOI: 10.1055/s-2006-950361
DOI: 10.1055/s-2006-950361
PAPER
© Georg Thieme Verlag Stuttgart · New York
New Approach for the Synthesis of c-di-GMP and Its Analogues
Further Information
Received
31 July 2006
Publication Date:
02 November 2006 (online)
Publication History
Publication Date:
02 November 2006 (online)
Abstract
The synthesis of cyclic bis(3′-5′)diguanylic acid (c-di-GMP) by using a new flexible approach is reported. The flexibility of the method is exemplified by the synthesis of base-modified analogues that will find applications in the elucidation of c-di-GMP biological modes of action.
Key words
c-di-GMP - nucleotide - cyclization - nucleobases - phosphotriester methodology
- 1
Jenal U. FEMS Microbiol. Rev. 2000, 24: 177 - 2
Paul R.Weiser S.Amiot N.Chan C.Schirmer T.Giese B.Jenal U. Genes Dev. 2004, 18: 715 - 3
Amikram D.Galperin MY. Bioinformatics 2006, 22: 3 - 4
Romling U.Gomelsky M.Galperin MY. Mol. Microbiol. 2005, 57: 629 - 5
Ryjenkov DA.Tarutina M.Moskovin OV.Gomelsky M. J. Bacteriol. 2005, 187: 1792 - 6
Ross P.Mayer R.Weinhouse H.Amikram D.Huggirat Y.Benziman M.de Vroom E.Fidder A.de Paus P.Sliedregt LAJM.van der Marel G.van Boom J. J. Biol. Chem. 1990, 265: 18933 - 7
Tischler A.Camilli A. Mol. Microbiol. 2004, 53: 857 - 8
Bobrov A.Kirillina O.Perry RD. FEMS Microbiol. Lett. 2005, 247: 123 - 9
Simm R.Morr M.Kader A.Nimtz M.Romling U. Mol. Microbiol. 2004, 53: 1123 - 10
Brouillette E.Hyodo M.Hayakawa Y.Karaolis DKR.Malouin F. Antimicrob. Agents Chemother. 2005, 49: 3109 - 11
Karaolis DKR.Cheng K.Lipsky M.Elnabawi A.Catalano J.Hyodo M.Hayakawa Y.Raufman JP. Biochem. Biophys. Res. Commun. 2005, 329: 40 - 12
Zhang Z.Gaffney BL.Jones RA. J. Am. Chem. Soc. 2004, 126: 16700 - 13
Hyodo M.Sato Y.Hayakawa Y. Tetrahedron 2006, 62: 3089 - 14
Hyodo M.Hayakawa Y. Bull. Chem. Soc. Jpn. 2004, 77: 2089 - 15
Serebryany V.Beigelman L. Tetrahedron Lett. 2002, 43: 1983 - 16
Ishihara K.Kurihara H.Yamamoto H. J. Org. Chem. 1993, 58: 3791 - 17
Parr IB.Horenstein BA. J. Org. Chem. 1997, 62: 7489 - 18
de Vroom E.Fidder A.Marugg JE.van der Marel GA.van Boom JH. Nucleic Acids Res. 1986, 14: 5885 - 19
DattaGupta A.Singh R.Singh VK. Synlett 1996, 69 - 20
Saito Y.Zevaco TA.Agrofoglio LA. Tetrahedron 2002, 58: 9593 - 21
Jenny F.Schneider KC.Benner SA. Nucleosides Nulceotides 1992, 11: 1257 - 22
Marwood RD.Shuto S.Jenkins DJ.Potter BVL. Chem. Commun. 2000, 219 - 23
Jenny TA.Benner SA. Tetrahedron Lett. 1992, 33: 6619 - 24
Chan C.Paul R.Samoray D.Amiot N.Giese B.Jenal U.Schirmer T. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 17084 - 25
Zhou J.Bouhadir KH.Webb TR.Shelvin PB. Tetrahedron Lett. 1997, 38: 4037