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Volumn 27, Issue 12, 2008, Pages 1282-1300

Design and synthesis of bis-carbamate analogs of cyclic bis-(3′-5′)-diguanylic acid (c-di-GMP) and the acyclic dimer PGPG

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; CYCLIC BIS (3',5') DIGUANYLIC ACID; DINUCLEOTIDE; UNCLASSIFIED DRUG;

EID: 55949131187     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770802554150     Document Type: Article
Times cited : (23)

References (40)
  • 1
    • 0001198852 scopus 로고
    • Control of cellulose synthesis in acetobacter xylinum. A unique guanyl oligonucleotide is the immediate activator of the cellulose synthase
    • Ross, P.A.Y.; Weinhouse, H.; Micheali, D.; Weinberher-Ohana, P.; Mayer, R.; Benziman, M. Control of cellulose synthesis in acetobacter xylinum. A unique guanyl oligonucleotide is the immediate activator of the cellulose synthase. Carbohydr. Res. 1986, 149, 101-117.
    • (1986) Carbohydr. Res , vol.149 , pp. 101-117
    • Ross, P.A.Y.1    Weinhouse, H.2    Micheali, D.3    Weinberher-Ohana, P.4    Mayer, R.5    Benziman, M.6
  • 2
    • 0025116425 scopus 로고
    • The cyclic diguanylic acid regulatory system of cellulose synthesis in Acetobacter xylinum. Chemical synthesis and biological activity of cyclic nucleotide dimer, trimer, and phosphothioate derivatives
    • Ross, P.; Mayer, R.; Weinhouse, H.; Amikam, D.; Huggirat, Y.; Benziman, M.; de Vroom, E.; Fidder, A.; de Paus, P.; Sliedregt, L.A.; et al. The cyclic diguanylic acid regulatory system of cellulose synthesis in Acetobacter xylinum. Chemical synthesis and biological activity of cyclic nucleotide dimer, trimer, and phosphothioate derivatives. J. Biol. Chem. 1990, 265(31), 18933-18943.
    • (1990) J. Biol. Chem , vol.265 , Issue.31 , pp. 18933-18943
    • Ross, P.1    Mayer, R.2    Weinhouse, H.3    Amikam, D.4    Huggirat, Y.5    Benziman, M.6    de Vroom, E.7    Fidder, A.8    de Paus, P.9    Sliedregt, L.A.10
  • 3
    • 26444582915 scopus 로고    scopus 로고
    • A chemosensory system that regulates biofilm formation through modulation of cyclic diguanylate levels
    • Hickman, J.W.; Tifrea, D.F.; Harwood, C.S. A chemosensory system that regulates biofilm formation through modulation of cyclic diguanylate levels. Proc. Natl. Acad. Sci U S A 2005, 102(40), 14422-14427.
    • (2005) Proc. Natl. Acad. Sci U S A , vol.102 , Issue.40 , pp. 14422-14427
    • Hickman, J.W.1    Tifrea, D.F.2    Harwood, C.S.3
  • 5
    • 34548303826 scopus 로고    scopus 로고
    • A cyclic-di-GMP receptor required for bacterial exopolysaccharide production
    • Lee, V.T.; Matewish, J.M.; Kessler, J.L.; Hyodo, M.; Hayakawa, Y.; Lory, S. A cyclic-di-GMP receptor required for bacterial exopolysaccharide production. Mol. Microbiol. 2007, 65(6), 1474-1484.
    • (2007) Mol. Microbiol , vol.65 , Issue.6 , pp. 1474-1484
    • Lee, V.T.1    Matewish, J.M.2    Kessler, J.L.3    Hyodo, M.4    Hayakawa, Y.5    Lory, S.6
  • 6
    • 4344688129 scopus 로고    scopus 로고
    • GGDEF and EAL domains inversely regulate cyclic di-GMP levels and transition from sessility to motility
    • Simm, R.; Morr, M.; Kader, A.; Nimtz, M.; Romling, U. GGDEF and EAL domains inversely regulate cyclic di-GMP levels and transition from sessility to motility. Mol. Microbiol. 2004, 53(4), 1123-1134.
    • (2004) Mol. Microbiol , vol.53 , Issue.4 , pp. 1123-1134
    • Simm, R.1    Morr, M.2    Kader, A.3    Nimtz, M.4    Romling, U.5
  • 7
    • 4444250897 scopus 로고    scopus 로고
    • M.S.; Cyclic di-GMP as a bacterial second messenger
    • D'Argenio DA, M.S.; Cyclic di-GMP as a bacterial second messenger. Microbiology 2004, 150(8), 2497-2502.
    • (2004) Microbiology , vol.150 , Issue.8 , pp. 2497-2502
    • D'Argenio, D.A.1
  • 9
    • 22644438480 scopus 로고    scopus 로고
    • The dawning of a novel bacterial signalling system
    • Romling, U.G.M.; Galperin, M.Y. C-di-GMP: The dawning of a novel bacterial signalling system. Mol. Microbiol. 2005, 57(3), 629-639.
    • (2005) Mol. Microbiol , vol.57 , Issue.3 , pp. 629-639
    • Romling, U.G.M.1    Galperin2    C-di-GMP, M.Y.3
  • 10
    • 34247213819 scopus 로고    scopus 로고
    • DgrA is a member of a new family of cyclic diguanosine monophosphate receptors and controls flagellar motor function in Caulobacter crescentus
    • Christen, M.; Christen, B.; Allan, M.G.; Folcher, M.; Jeno, P.; Grzesiek, S.; Jenal, U. DgrA is a member of a new family of cyclic diguanosine monophosphate receptors and controls flagellar motor function in Caulobacter crescentus. Proc. Natl. Acad. Sci. USA 2007, 104(10), 4112-4117.
    • (2007) Proc. Natl. Acad. Sci. USA , vol.104 , Issue.10 , pp. 4112-4117
    • Christen, M.1    Christen, B.2    Allan, M.G.3    Folcher, M.4    Jeno, P.5    Grzesiek, S.6    Jenal, U.7
  • 11
    • 42149119716 scopus 로고    scopus 로고
    • Role of cyclic Di-GMP during el tor biotype Vibrio cholerae infection: Characterization of the in vivo-induced cyclic Di-GMP phosphodiesterase CdpA
    • Tamayo, R.; Schild, S.; Pratt, J.T.; Camilli, A. Role of cyclic Di-GMP during el tor biotype Vibrio cholerae infection: Characterization of the in vivo-induced cyclic Di-GMP phosphodiesterase CdpA. Infect. Immun. 2008, 76(4), 1617-1627.
    • (2008) Infect. Immun , vol.76 , Issue.4 , pp. 1617-1627
    • Tamayo, R.1    Schild, S.2    Pratt, J.T.3    Camilli, A.4
  • 12
    • 34547178695 scopus 로고    scopus 로고
    • Cell-cell signaling, cyclic di-GMP turnover and regulation of virulence in Xanthomonas campestris
    • Fouhy, Y.; Lucey, J.F.; Ryan, R.P.; Dow, J.M. Cell-cell signaling, cyclic di-GMP turnover and regulation of virulence in Xanthomonas campestris. Res. Microbiol. 2006, 157(10), 899-904.
    • (2006) Res. Microbiol , vol.157 , Issue.10 , pp. 899-904
    • Fouhy, Y.1    Lucey, J.F.2    Ryan, R.P.3    Dow, J.M.4
  • 13
    • 33845403359 scopus 로고    scopus 로고
    • Mechanisms of cyclic-di-GMP signaling in bacteria
    • Jenal, U.; Malone, J. Mechanisms of cyclic-di-GMP signaling in bacteria. Annu. Rev. Genet. 2006, 40, 385-407.
    • (2006) Annu. Rev. Genet , vol.40 , pp. 385-407
    • Jenal, U.1    Malone, J.2
  • 14
    • 4744337730 scopus 로고    scopus 로고
    • Kirillina, O.; Fetherston, J.D.; Bobrov, A.G.; Abney, J.; Perry, R.D. HmsP, a putative phosphodiesterase, and HmsT, a putative diguanylate cyclase, control Hms-dependent biofilm formation in Yersinia pestis. Mol. Microbiol. 2004, 54(1), 75-88.
    • Kirillina, O.; Fetherston, J.D.; Bobrov, A.G.; Abney, J.; Perry, R.D. HmsP, a putative phosphodiesterase, and HmsT, a putative diguanylate cyclase, control Hms-dependent biofilm formation in Yersinia pestis. Mol. Microbiol. 2004, 54(1), 75-88.
  • 15
    • 34247202706 scopus 로고    scopus 로고
    • The structure-function relationship of WspR, a Pseudomonas fluorescens response regulator with a GGDEF output domain
    • Malone, J.G.; Williams, R.; Christen, M.; Jenal, U.; Spiers, A.J.; Rainey, P.B. The structure-function relationship of WspR, a Pseudomonas fluorescens response regulator with a GGDEF output domain. Microbiology 2007, 153(Pt 4), 980-994.
    • (2007) Microbiology , vol.153 , Issue.PART 4 , pp. 980-994
    • Malone, J.G.1    Williams, R.2    Christen, M.3    Jenal, U.4    Spiers, A.J.5    Rainey, P.B.6
  • 16
    • 0035254950 scopus 로고    scopus 로고
    • GGDEF domain is homologous to adenylyl cyclase
    • Pei, J.; Grishin, N.V. GGDEF domain is homologous to adenylyl cyclase. Proteins 2001, 42(2), 210-216.
    • (2001) Proteins , vol.42 , Issue.2 , pp. 210-216
    • Pei, J.1    Grishin, N.V.2
  • 21
    • 30344469912 scopus 로고    scopus 로고
    • PilZ domain is part of the bacterial c-di-GMP binding protein
    • Amikam, D.; Galperin, M.Y. PilZ domain is part of the bacterial c-di-GMP binding protein. Bioinformatics 2006, 22(1), 3-6.
    • (2006) Bioinformatics , vol.22 , Issue.1 , pp. 3-6
    • Amikam, D.1    Galperin, M.Y.2
  • 23
    • 34250358327 scopus 로고    scopus 로고
    • PilZ domain proteins bind cyclic diguanylate and regulate diverse processes in Vibrio cholerae
    • Pratt, J.T.; Tamayo, R.; Tischler, A.D.; Camilli, A. PilZ domain proteins bind cyclic diguanylate and regulate diverse processes in Vibrio cholerae. J. Biol. Chem. 2007, 282(17), 12860-12870.
    • (2007) J. Biol. Chem , vol.282 , Issue.17 , pp. 12860-12870
    • Pratt, J.T.1    Tamayo, R.2    Tischler, A.D.3    Camilli, A.4
  • 27
    • 13844262033 scopus 로고    scopus 로고
    • c-di-GMP (3′-5′-cyclic diguanylic acid) inhibits Staphylococcus aureus cell-cell interactions and biofilm formation
    • Karaolis, D.K.; Rashid, M.H.; Chythanya, R.; Luo, W.; Hyodo, M.; Hayakawa, Y. c-di-GMP (3′-5′-cyclic diguanylic acid) inhibits Staphylococcus aureus cell-cell interactions and biofilm formation. Antimicrob. Agents Chemother. 2005, 49(3), 1029-1038.
    • (2005) Antimicrob. Agents Chemother , vol.49 , Issue.3 , pp. 1029-1038
    • Karaolis, D.K.1    Rashid, M.H.2    Chythanya, R.3    Luo, W.4    Hyodo, M.5    Hayakawa, Y.6
  • 28
    • 35848951876 scopus 로고    scopus 로고
    • Roles of cyclic diguanylate in the regulation of bacterial pathogenesis
    • Tamayo, R.; Pratt, J.T.; Camilli, A. Roles of cyclic diguanylate in the regulation of bacterial pathogenesis. Annu. Rev. Microbiol. 2007, 61, 131-148.
    • (2007) Annu. Rev. Microbiol , vol.61 , pp. 131-148
    • Tamayo, R.1    Pratt, J.T.2    Camilli, A.3
  • 29
    • 33644686004 scopus 로고    scopus 로고
    • Yuma; Hayakawa, Yoshihiro. Synthesis of cyclic bis(3′-5′)diguanylic acid (c-di-GMP) analogs
    • Hyodo, M.i.S.; Yuma; Hayakawa, Yoshihiro. Synthesis of cyclic bis(3′-5′)diguanylic acid (c-di-GMP) analogs. Tetrahedron 2006, 62, 3089-3094.
    • (2006) Tetrahedron , vol.62 , pp. 3089-3094
    • Hyodo, M.I.S.1
  • 30
  • 31
    • 33744904451 scopus 로고    scopus 로고
    • Polymorphism of the signaling molecule c-di-GMP
    • Zhang, Z.; Kim, S.; Gaffney, B.L.; Jones, R.A. Polymorphism of the signaling molecule c-di-GMP. J. Am. Chem. Soc. 2006, 128(21), 7015-1024.
    • (2006) J. Am. Chem. Soc , vol.128 , Issue.21 , pp. 7015-1024
    • Zhang, Z.1    Kim, S.2    Gaffney, B.L.3    Jones, R.A.4
  • 32
    • 49649083608 scopus 로고    scopus 로고
    • Synthesis of Cyclic Bis(3′-5′)-2′-deoxyguanylic/guanylic Acid (c-dGpGp) and Its Biological Activities to Microbes
    • Mano, E.; Hyodo, M.; Sato, Y.; Ishihara, Y.; Ohta, M.; Hayakawa, Y. Synthesis of Cyclic Bis(3′-5′)-2′-deoxyguanylic/guanylic Acid (c-dGpGp) and Its Biological Activities to Microbes. Chem. Med. Chem. 2007, 2(10), 1410-1413.
    • (2007) Chem. Med. Chem , vol.2 , Issue.10 , pp. 1410-1413
    • Mano, E.1    Hyodo, M.2    Sato, Y.3    Ishihara, Y.4    Ohta, M.5    Hayakawa, Y.6
  • 33
    • 33845400857 scopus 로고    scopus 로고
    • Cyclic di-GMP signaling in bacteria: Recent advances and new puzzles
    • Ryan, R.P.; Fouhy, Y.; Lucey, J.F.; Dow, J.M. Cyclic di-GMP signaling in bacteria: Recent advances and new puzzles. J. Bacteriol. 2006, 188(24), 8327-8334.
    • (2006) J. Bacteriol , vol.188 , Issue.24 , pp. 8327-8334
    • Ryan, R.P.1    Fouhy, Y.2    Lucey, J.F.3    Dow, J.M.4
  • 34
    • 0028353670 scopus 로고
    • Synthesis of oligodeoxyribnonucleotides containing dimers with carbamate moieties as replacement of the natural phosphodiester linkage
    • Waldner, A.D.M. A.; Lebreton, J. Synthesis of oligodeoxyribnonucleotides containing dimers with carbamate moieties as replacement of the natural phosphodiester linkage. Bioorg. Med. Chem. Lett. 1994, 4(3), 405-408.
    • (1994) Bioorg. Med. Chem. Lett , vol.4 , Issue.3 , pp. 405-408
    • Waldner, A.D.M.A.1    Lebreton, J.2
  • 35
    • 20044364380 scopus 로고    scopus 로고
    • Organic carbamates in drug development. Part II: Antimicrobial agents-Recent reports
    • Ray, S.P. S.; Chaturvedi, D. Organic carbamates in drug development. Part II: Antimicrobial agents-Recent reports. Drugs of the Future 2005, 30(2), 161-180.
    • (2005) Drugs of the Future , vol.30 , Issue.2 , pp. 161-180
    • Ray, S.P.S.1    Chaturvedi, D.2
  • 36
    • 9744261694 scopus 로고    scopus 로고
    • Hyodo, M.H.Y. An Improved method for synthesizing cyclic bis(3′-5′)diguanylic acid (c-di-GMP). Bull. Chem. Soc. Jpn. 2004, 77, 2089-2093.
    • Hyodo, M.H.Y. An Improved method for synthesizing cyclic bis(3′-5′)diguanylic acid (c-di-GMP). Bull. Chem. Soc. Jpn. 2004, 77, 2089-2093.
  • 39
    • 0031181346 scopus 로고    scopus 로고
    • Powerful, rapid computer algorithms for structure-based drug design
    • McMartin, C.; Bohacek, R.S. QXP: Powerful, rapid computer algorithms for structure-based drug design. J. Comput. Aided Mol. Des. 1997, 11(4), 333-344.
    • (1997) J. Comput. Aided Mol. Des , vol.11 , Issue.4 , pp. 333-344
    • McMartin, C.1    Bohacek, R.S.Q.2
  • 40
    • 55949100061 scopus 로고    scopus 로고
    • QXP/FLO, version 99.6; ThistleSoft Inc. Colebrook, CT, USA, 1999
    • QXP/FLO, version 99.6; ThistleSoft Inc. Colebrook, CT, USA, 1999.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.