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Bioscience, Biotechnology, and Biochemistry Volume 75, 2011 - Issue 8
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Original Articles

Synthesis of Microbial Signaling Molecules and Their Stereochemistry-Activity Relationships

Arata YAJIMADepartment of Fermentation Science, Faculty of Applied Biological Science, Tokyo University of Agriculture (NODAI)
Pages 1418-1429 | Published online: 22 May 2014

  • 1) Fuqua WC, Winans SC, and Greenberg EP, J. Bacteriol., 176, 269–275 (1994).
  • 2) Bassler BL and Losick R, Cell, 125, 237–246 (2006).
  • 3) Nealson KH, Platt T, and Hastings JW, J. Bacteriol., 104, 313–322 (1970).
  • 4) Eberhard A, Burlingame AL, Eberhard C, Kenyon GL, Nealson KH, and Oppenheimer NJ, Biochemistry, 20, 2444–2449 (1981).
  • 5) Okada M, Qi J, and Sakagami Y, Mycotoxins, 59, 55–66 (2009).
  • 6) Katayama M and Marumo S, Agric. Biol. Chem., 42, 505–506 (1978).
  • 7) Tanaka S, Wada K, Marumo S, and Hattori H, Tetrahedron Lett., 25, 5907–5910 (1984).
  • 8) McMorris TC and Barksdale AW, Nature, 215, 320–321 (1967).
  • 9) Arsenault GP, Biemann K, Barksdale AW, and McMorris TC, J. Am. Chem. Soc., 90, 5635–5636 (1968).
  • 10) Raper JR, Am. J. Bot., 26, 639–650 (1939).
  • 11) McMorris TC, Seshadri R, Weihe GR, Arsenault GP, and Barksdale AW, J. Am. Chem. Soc., 97, 2544–2545 (1975).
  • 12) Khokhlov AS, Tovarova II, Borisova LN, Pliner SA, Shevchenko LA, Kornitskaya EY, Ivkina NS, and Rapoport IA, Dokl. Akad. Nauk SSSR, 177, 232–235 (1967).
  • 13) Hara O and Beppu T, J. Antibiot., 35, 349–358 (1982).
  • 14) Hara O and Beppu T, J. Antibiot., 35, 1208–1215 (1982).
  • 15) Kawai G and Ikeda Y, Biochim. Biophys. Acta, 754, 243–248 (1983).
  • 16) Uno I and Ishikawa T, J. Bacteriol., 113, 1240–1248 (1973).
  • 17) Higgins DA, Pomianek ME, Kraml CM, Taylor RK, Semmelhack MF, and Bassler BL, Nature, 450, 883–886 (2007).
  • 18) Wei Y, Perez LJ, Ng W-L, Semmelhack MF, and Bassler BL, ACS Chem. Biol., 6, 356–365 (2011).
  • 19) Xavier KB and Bassler BL, Curr. Opin. Microbiol., 6, 191–197 (2003).
  • 20) Bassler BL, Wright M, Showalter RE, and Silverman MR, Mol. Microbiol., 9, 773–786 (1993).
  • 21) Chen X, Schauder S, Potier N, van Dorsselaer A, Pelczer I, Bassler BL, and Hughson FM, Nature, 415, 545–549 (2002).
  • 22) Miller ST, Xavier KB, Campagna SR, Taga ME, Semmelhack MF, Bassler BL, and Hughson FM, Mol. Cell, 15, 677–687 (2004).
  • 23) Meijler MM, Hom LG, Kaufmann GF, McKenzie KM, Sun C, Moss JA, Matsushita M, and Janda KD, Angew. Chem. Int. Ed., 43, 2106–2108 (2004).
  • 24) Corey EJ and Fuchs PL, Tetrahedron Lett., 13, 3769–3772 (1972).
  • 25) Schauder S, Shokat K, Surette MG, and Bassler BL, Mol. Microbiol., 41, 463–476 (2001).
  • 26) Winzer K, Hardie KR, Burgess N, Doherty N, Kirke D, Holden MTG, Linforth R, Cornell KA, Taylor AJ, Hill PJ, and Williams P, Microbiology, 148, 909–922 (2002).
  • 27) Semmelhack MF, Campagna SR, Federle MJ, and Bassler BL, Org. Lett., 7, 569–572 (2005).
  • 28) Lowery CA, McKenzie KM, Qi L, Meijler MM, and Janda KD, Bioorg. Med. Chem. Lett., 15, 2395–2398 (2005).
  • 29) de Keersmaecker SCJ, Varszegi C, van Boxel N, Habel LW, Metzger K, Daniels R, Marchal K, de Vos D, and Vanderleyden J, J. Biol. Chem., 280, 19563–19568 (2005).
  • 30) Kadirvel M, Stimpson WT, Moumene-Afifi S, Arsic B, Glynn N, Halliday N, Williams P, Gilbert P, McBain AJ, Freeman S, and Gardiner JM, Bioorg. Med. Chem. Lett., 20, 2625–2628 (2010).
  • 31) Frezza M, Soulére L, Queneau Y, and Doutheau A, Tetrahedron Lett., 46, 6495–6498 (2005).
  • 32) Morita K, Suzuki Z, and Hirose H, Bull. Chem. Soc. Jpn., 41, 2815 (1968).
  • 33) Ascenso OS, Marques JC, Santos AR, Xavier KB, Ventura MR, and Maycock CD, Bioorg. Med. Chem., 19, 1236–1241 (2011).
  • 34) Midland MM, Tramontano A, and Zderic SA, J. Am. Chem. Soc., 99, 5211–5213 (1977).
  • 35) Moré MI, Finger LD, Stryker JL, Fuqua C, Eberhard A, and Winans SC, Science, 272, 1655–1658 (1996).
  • 36) Tomasz A, Nature, 208, 155–159 (1965).
  • 37) Fuqua C, Winans SC, and Greenberg EP, Annu. Rev. Microbiol., 50, 727–751 (1996).
  • 38) Williams P, Winzer K, Chan WC, and Cámara M, Philos. Trans. R. Soc. B, 362, 1119–1134 (2007).
  • 39) Schripsema J, de Rudder KEE, van Vliet TB, Lankhorst PP, de Vroom E, Kijne JW, and van Brussel AAN, J. Bacteriol., 178, 366–371 (1996).
  • 40) Gray KM, Pearson JP, Downie JA, Boboye BEA, and Greenberg EP, J. Bacteriol., 178, 372–376 (1996).
  • 41) Kijne JW, “Biological Nitrogen Fixation,” eds. Stacey G, Burris RH, and Evans HJ, Chapman and Hall, London, pp. 349–398 (1992).
  • 42) Rodelas B, Lithgow JK, Wisniewski-Dye F, Hardman A, Wilkinson A, Economou A, Williams P, and Downie JA, J. Bacteriol., 181, 3816–3823 (1999).
  • 43) Thorne SH and Williams HD, J. Bacteriol., 181, 981–990 (1999).
  • 44) Lithgow JK, Willkinson A, Hardman A, Rodelas B, Wisniewski-Dye F, Williams P, and Downie JA, Mol. Microbiol., 37, 81–97 (2000).
  • 45) Blosser-Middleton RS and Gray KM, J. Bacteriol., 183, 6771–6777 (2001).
  • 46) Hirsch PR, J. Gen. Microbiol., 113, 219–228 (1979).
  • 47) Laue BE, Jiang Y, Chhabra SR, Jacob S, Stewart GSAB, Hardman A, Downie JA, O’Gara F, and Williams P, Microbiology, 146, 2469–2480 (2000).
  • 48) Yajima A, van Brussel AAN, Schripsema J, Nukada T, and Yabuta G, Org. Lett., 10, 2047–2050 (2008).
  • 49) Choi J and Yoon N-M, Tetrahedron Lett., 37, 1057–1060 (1996).
  • 50) Nagao Y, Hagiwara Y, Kumagai T, Ochiai M, Inoue T, Hashimoto K, and Fujita E, J. Org. Chem., 51, 2391–2393 (1986).
  • 51) Nagao Y, Dai W-M, Ochiai M, and Shiro M, J. Org. Chem., 54, 5211–5217 (1989).
  • 52) Smith TE, Djang M, Velander AJ, Downey CW, Carroll KA, and van Alphen S, Org. Lett., 6, 2317–2320 (2004).
  • 53) Laus MC, van Brussel AAN, and Kijne JW, Mol. Plant Microb Interact., 18, 533–538 (2005).
  • 54) Wilkinson A, Danino V, Wisniewski-Dyé F, Lithgow JK, and Downie JA, J. Bacteriol., 184, 4510–4519 (2002).
  • 55) Kumaraswamy G and Jayaprakash N, Tetrahedron Lett., 51, 6500–6502 (2010).
  • 56) Matsumura K, Hashiguchi S, Ikariya T, and Nayori R, J. Am. Chem. Soc., 119, 8738–8739 (1997).
  • 57) Trost BM, Malhotra S, and Fried BA, J. Am. Chem. Soc., 131, 1674–1675 (2009).
  • 58) Holmquist CR and Roskamp EJ, J. Org. Chem., 54, 3258–3260 (1989).
  • 59) Hamada T, Torii T, Izawa K, Nayori R, and Ikariya T, Org. Lett., 4, 4373–4376 (2002).
  • 60) Dow JM, Scofield G, Trafford K, Turner PC, and Daniels MJ, Physiol. Mol. Plant Pathol., 31, 261–271 (1987).
  • 61) Dums F, Dow JM, and Daniels MJ, Mol. Gen. Genet., 229, 357–364 (1991).
  • 62) Barber CE, Tang JL, Feng JX, Pan MQ, Wilson TJG, Slater H, Dow JM, Williams P, and Daniels MJ, Mol. Microbiol., 24, 555–566 (1997).
  • 63) Wang L-H, He Y, Gao Y, Wu J-E, Dong Y-H, He C, Wang S-X, Weng L-X, Xu J-L, Tay L, Fang R-X, and Zhang L-H, Mol. Microbiol., 51, 903–912 (2004).
  • 64) He Y-W, Wang C, Zhou L, Song H, Dow JM, and Zhang L-H, J. Biol. Chem., 281, 33414–33421 (2006).
  • 65) Deng Y, Wu J, Tao F, and Zhang L-H, Chem. Rev., 111, 160–173 (2011).
  • 66) Chun W, Cui J, and Poplawsky AR, Physiol. Mol. Plant Pathol., 51, 1–14 (1997).
  • 67) Poplawsky AR and Chun W, Mol. Plant Microbe Interact., 11, 466–475 (1998).
  • 68) Yajima A, Imai N, Poplawsky AR, Nukada T, and Yabuta G, Tetrahedron Lett., 51, 2074–2077 (2010).
  • 69) Mori K and Koseki K, Tetrahedron, 44, 6013–6020 (1988).
  • 70) Evans DA and Weber AE, J. Am. Chem. Soc., 108, 6757–6761 (1986).
  • 71) Poplawsky AR and Chun W, J. Bacteriol., 179, 439–444 (1997).
  • 72) Poplawsky AR, Walters DM, Rouviere PE, and Chun W, Mol. Plant Pathol., 6, 653–657 (2005).
  • 73) Erwin DC and Riberio OK, “Phytophthora Diseases Worldwide,” The American Phytopathological Society, St. Paul (1996).
  • 74) Fry WE and Goodwin SB, Bioscience, 47, 363–371 (1997).
  • 75) Lane CR, Beales PA, Hughes KJD, Griffin RL, Munro D, Brasier CM, and Webber JF, Plant Pathol., 52, 414 (2003).
  • 76) Ashby SF, Trans. Br. Mycol. Soc., 14, 18–38 (1929).
  • 77) Galloway LD, Sci. Repts. Agr. Res. Inst., Pusa, 1934–1935, 120–130 (1936).
  • 78) Kouyeas V, Ann. Inst. Phytopathol. Benaki, 7, 40–53 (1953).
  • 79) Ko WH, J. Gen. Microbiol., 107, 15–18 (1978).
  • 80) Stamps DJ, Trans. Br. Mycol. Soc., 36, 255–259 (1953).
  • 81) Apple JL, Phytopathology, 49, 37–43 (1959).
  • 82) Haasis FA and Nelson RR, Plant Dis. Rep., 47, 705–709 (1963).
  • 83) Marx DH, Haasis FA, and Nelson RR, J. Elisha Mitchell Sci. Soc., 81, 75–76 (1965).
  • 84) Brasier CM, Trans. Br. Mycol. Soc., 58, 237–251 (1972).
  • 85) Chang ST, Shepherd CJ, and Pratt BH, Aust. J. Bot., 22, 669– 679 (1974).
  • 86) Ko WH, J. Gen. Microbiol., 129, 1397–1401 (1983).
  • 87) Chern LL, Tang CS, and Ko WH, Bot. Bull. Acad. Sin., 40, 79–85 (1999).
  • 88) Qi J, Asano T, Jinno M, Matsui K, Atsumi K, Sakagami Y, and Ojika M, Science, 309, 1828 (2005).
  • 89) Yajima A, Kawanishi N, Qi J, Asano T, Sakagami Y, Nukada T, and Yabuta G, Tetrahedron Lett., 48, 4601–4603 (2007).
  • 90) Bajpai R, Yang F, and Curran DP, Tetrahedron Lett., 48, 7965–7968 (2007).
  • 91) Ohtani I, Kusumi T, Kashman Y, and Kakisawa H, J. Am. Chem. Soc., 113, 4092–4096 (1991).
  • 92) Ojika M, Qi J, Kito Y, and Sakagami Y, Tetrahedron: Asymmetry, 18, 1763–1765 (2007).
  • 93) Yajima A, Qin Y, Zhou X, Kawanishi N, Xiao X, Wang J, Zhang D, Wu Y, Nukada T, Yabuta G, Qi J, Asano T, and Sakagami Y, Nat. Chem. Biol., 4, 235–237 (2008).
  • 94) Nakai T, Yajima A, Akasaka K, Kaihoku T, Ohtaki M, Nukada T, Ohrui H, and Yabuta G, Biosci. Biotechnol. Biochem., 69, 2401–2408 (2005).
  • 95) Kolb HC, van Nieuwenhze MS, and Sharpless KB, Chem. Rev., 94, 2483–2547 (1994).
  • 96) Dess DB and Martin JC, J. Org. Chem., 48, 4155–4156 (1983).
  • 97) Harutyunyan SR, Zhao Z, den Hartog T, Bouwmeester K, Minnaard AJ, and Feringa BL, Proc. Natl. Acad. Sci. USA, 105, 8507–8512 (2008).
  • 98) Denmark SE, Heemstra JRJr, and Beutner GL, Angew. Chem. Int. Ed., 44, 4682–4698 (2005).
  • 99) Wang S-Y, Song P, Chan L-Y, and Loh T-P, Org. Lett., 12, 5166–5169 (2010).
  • 100) Blackwell HE, O’Leary DJ, Chatterjee AK, Washenfelder RA, Bussmann DA, and Grubbs RH, J. Am. Chem. Soc., 122, 58–71 (2000).

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