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Synopsis of Structural, Biosynthetic, and Chemical Aspects of Glycopeptide Antibiotics

Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 267)

Abstract

Glycopeptide antibiotics represent a very important group of natural products with regard to medicinal application as antibacterials and for cancer treatment. A characteristic for assignment as a glycopeptide antibiotic, next to antibiotic potential, is the modification of the peptide aglycon with various types of carbohydrates. According to this definition, vancomycin (including five subtypes), ramoplanin, bleomycin, mannopeptimycins and salmochelin belong to the family of glycopeptide antibiotics. In this article, an overview is given on the structural aspects, the biosynthesis and the mode of action of glycopeptide antibiotics. Structure–activity relationships of important functional groups contributing to enhanced antibiotic properties are highlighted. Finally, similarities with regard to structural features, the biosyntheses and the modes of actions are discussed. According to current knowledge, glycopeptide antibiotics mostly act as inhibitors of bacterial cell wall biosynthesis. It is to be expected that the actual list of glycopeptides will be continuously extended due to discoveries from ongoing screening programs.

Bleomycin Mannopeptimycin Ramoplanin Salmochelin Vancomycin 

Abbreviations

ACP

Acyl carrier protein

BLM

Bleomycin

Chp

3-Chloro-4-hydroxyphenylglycine

Dab

2,4-Diaminobutyric acid

Dhb

2,3-Dihydroxybenzoic acid

Dpg

3,5-Dihydroxyphenylglycine

Dpr

2,3-Diaminopropionic acid

FTICR

Fourier transform ion cyclotron resonance

Hpg

4-Hydroxyphenylglycine

Hty

β-Hydroxytyrosine

Mephe

β-Methylphenylalanine

MIC

Minimum inhibitory concentration

MPM

Mannopeptimycin

MRSA

Methicillin-resistant Staphylococcus aureus

NRPS

Non-ribosomal peptide synthetase

orf

Open reading frame

PBA

Pyrimidoblamic acid

PBP

Penicillin binding protein

PKS

Polyketide synthase

SAR

Structure–activity relationship

VRE

Vancomycin-resistant enterococci

VRSA

Vancomycin-resistant Staphylococcus aureus

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Notes

Acknowledgments

This work was supported by a grant of the European Union (COMBIG-TOP, LSHG-CT-2003-503491), the Deutsche Forschungsgemeinschaft (DFG, SU 239/3-3) and by an Emmy-Noether-Fellowship for young investigators of the DFG (SU 239/2-2).

References

  1. 1.
    Sharon N (1986) Eur J Biochem 159:1 Google Scholar
  2. 2.
    Sieber SA, Marahiel MA (2005) Chem Rev 105:715 Google Scholar
  3. 3.
    McCormick MH, Stark WM, Pittenger GE, Pittenger RC, McGuire JM (1955-1956) Antibiot Annu 606 Google Scholar
  4. 4.
    Sheldrick GM, Jones PG, Kennard O, Williams DH, Smith GA (1978) Nature 271:223 Google Scholar
  5. 5.
    Williams DH, Kalman JR (1977) J Am Chem Soc 99:2768 Google Scholar
  6. 6.
    Harris CM, Harris TM (1982) J Am Chem Soc 104:4293 Google Scholar
  7. 7.
    Nicolaou KC, Natarajan S, Li H, Jain NF, Hughes R, Solomon ME, Ramanjulu JM, Boddy CNC, Takayanagi M (1998) Angew Chem 110:2872, Angew Chem Int Ed 37:2708 Google Scholar
  8. 8.
    Nicolaou KC, Jain NF, Natarajan S, Hughes R, Solomon ME, Li H, Ramanjulu JM, Takayanagi M, Koumbis AE, Bando T (1998) Angew Chem 110:2879, Angew Chem Int Ed 37:2714 Google Scholar
  9. 9.
    Nicolaou KC, Takayanagi M, Jain NF, Natarajan S, Koumbis AE, Bando, Ramanjulu JM (1998) Angew Chem 110:2881, Angew Chem Int Ed 37:2717 Google Scholar
  10. 10.
    Evans DA, Wood MR, Trotter BW, Richardson TI, Barrow JC, Katz JL (1998) Angew Chem 110:2864, Angew Chem Int Ed 37:2700 Google Scholar
  11. 11.
    Boger DL, Miyazaki S, Kim SH, Wu JH, Loiseleur O, Castle SL (1999) J Am Chem Soc 121:3226 Google Scholar
  12. 12.
    Nicolaou KC, Boddy CNC, Bräse S, Winssinger N (1999) Angew Chem 111:2230, Angew Chem Int Ed 38:2096 Google Scholar
  13. 13.
    Nicolaou KC, Snyder SA (2003) Classics in total synthesis II. Wiley, Weinheim Google Scholar
  14. 14.
    Boger DL, Kim SH, Mori Y, Weng JH, Rogel O, Castle SL, McAtee JJ (2001) J Am Chem Soc 123:1862 Google Scholar
  15. 15.
    Matsuzaki K, Ikeda H, Ogino T, Matsumoto A, Woodruff HB, Tanaka H, Omura S (1994) J Antibiot 47:1173 Google Scholar
  16. 16.
    Perkins HR (1969) Biochem J 111:195 Google Scholar
  17. 17.
    Williams DH, Williamson MP, Butcher DW, Hammond SJ (1983) J Am Chem Soc 105:1332 Google Scholar
  18. 18.
    Nieto A, Perkins HR (1971) Biochem J 123:773 Google Scholar
  19. 19.
    Waltho JP, Williams DH (1989) J Am Chem Soc 111:2475 Google Scholar
  20. 20.
    Batta G, Sztaricskai F, Kover KE, Rudel C, Berdnikova TFJ (1991) J Antibiot 44:1208 Google Scholar
  21. 21.
    Loll PJ, Bevivino AE, Korty BD, Axelsen PH (1997) J Am Chem Soc 119:1516 Google Scholar
  22. 22.
    Mackay JP, Gerhard U, Beauregard DA, Westwell MS, Searle MS, Williams DH (1994) J Am Chem Soc 116:4581 Google Scholar
  23. 23.
    Williams DH, Maguire AJ, Tsuzuki W, Westwell MS (1998) Science 280:711 Google Scholar
  24. 24.
    Shiozawa H, Chia BCS, Davies NL, Zerella R, Williams DH (2001) J Am Chem Soc 124:3914 Google Scholar
  25. 25.
    Williams DH, Bardsley B (1999) Angew Chem 111:1264, Angew Chem Int Ed 38:1172 Google Scholar
  26. 26.
    Uttley AH, Collins CH, Naidoo J, George RC (1988) Lancet 1:57 Google Scholar
  27. 27.
    Hiramatsu K, Hanaki H, Ino T, Yabuta K, Oguri T, Tenover FC (1997) J Antimicrob Chemother 40:135 Google Scholar
  28. 28.
    Cetinkaya Y, Falk P, Mayhall CG (2000) Clin Microbiol Rev 13:686 Google Scholar
  29. 29.
    Allen NE, Nicas TI (2003) FEMS Microbiol Rev 26:511 Google Scholar
  30. 30.
    Hubbard BK, Walsh CT (2003) Angew Chem 115:752, Angew Chem Int Ed 42:730 Google Scholar
  31. 31.
    Süssmuth RD, Wohlleben W (2004) Appl Microb Biotech 63:344 Google Scholar
  32. 32.
    Pelzer S, Reichert W, Huppert M, Heckmann D, Wohlleben W (1997) J Biotech 56:115 Google Scholar
  33. 33.
    Pelzer S, Süssmuth RD, Heckmann D, Recktenwald J, Huber P, Jung G, Wohlleben W (1999) Antimicrob Agents Chemother 43:1565 Google Scholar
  34. 34.
    van Wageningen AMA, Kirkpatrick PN, Williams DH, Harris BR, Kershaw JK, Lennard NJ, Jones M, Jones SJM, Solenberg PJ (1998) Chem Biol 5:155 Google Scholar
  35. 35.
    Li TL, Huang F, Haydock SF, Mironenko T, Leadlay PF, Spencer JB (2004) Chem Biol 11:107 Google Scholar
  36. 36.
    Sosio M, Kloosterman H, Bianchi A, de Vreugd P, Dijkhuizen L, Donadio S (2004) Microbiology 150:95 Google Scholar
  37. 37.
    Chiu HT, Hubbard BK, Shah AN, Eide J, Fredenburg RA, Walsh CT, Khosla C (2001) Proc Natl Acad Sci USA 98:8548 Google Scholar
  38. 38.
    Choroba OW, Williams DH, Spencer JB (2000) J Am Chem Soc 122:5389 Google Scholar
  39. 39.
    Hubbard BK, Thomas MG, Walsh CT (2000) Chem Biol 42:1 Google Scholar
  40. 40.
    Li TL, Choroba OW, Hong H, Williams DH, Spencer JB (2001) J Chem Soc Chem Commun 20:2156 Google Scholar
  41. 41.
    Pfeifer V, Nicholson GJ, Ries J, Recktenwald J, Schefer AB, Shawky RM, Schröder J, Wohlleben W, Pelzer S (2001) J Biol Chem 276:38370 Google Scholar
  42. 42.
    Chen H, Tseng CC, Hubbard BK, Walsh CT (2001) Proc Natl Acad Sci USA 98:14901 Google Scholar
  43. 43.
    Puk O, Bischoff D, Kittel C, Pelzer S, Weist S, Stegmann E, Süssmuth RD, Wohlleben W (2004) J Bacteriol 186:6093 Google Scholar
  44. 44.
    Puk O, Huber P, Bischoff D, Recktenwald J, Jung G, Süssmuth RD (2002) Chem Biol 9:225 Google Scholar
  45. 45.
    Chen H, Walsh CT (2001) Chem Biol 74:1 Google Scholar
  46. 46.
    Bischoff D, Bister B, Bertazzo M, Pfeifer V, Stegmann E, Nicholson GJ, Keller S, Pelzer S, Wohlleben W, Süssmuth RD (2005) ChemBioChem 6:267 Google Scholar
  47. 47.
    Chen H, Thomas MG, Hubbard BK, Losey HC, Walsh CT, Burkart MD (2000) Proc Natl Acad Sci USA 96:11942 Google Scholar
  48. 48.
    Bischoff D, Pelzer S, Höltzel A, Nicholson GJ, Stockert S, Wohlleben W, Jung G, Süssmuth RD (2001) Angew Chem 113:1736, Angew Chem Int Ed 40:1693 Google Scholar
  49. 49.
    Bischoff D, Pelzer S, Bister B, Nicholson GJ, Stockert S, Schirle M, Wohlleben W, Jung G, Süssmuth RD (2001) Angew Chem 113:4824, Angew Chem Int Ed 40:4688 Google Scholar
  50. 50.
    Pylypenko O, Vitali F, Zerbe K, Robinson JA, Schlichting I (2003) J Biol Chem 278:46727 Google Scholar
  51. 51.
    Zerbe K, Pylypenko O, Vitali F, Zhang W, Rouset S, Heck M, Vrijbloed JW, Bischoff D, Bister B, Süssmuth RD, Pelzer S, Wohlleben W, Robinson JA, Schlichting I (2002) J Biol Chem 277:47476 Google Scholar
  52. 52.
    Zerbe K, Woithe K, Li DB, Vitali F, Bigler L, Robinson JA (2004) Angew Chem 116:6877, Angew Chem Int Ed 43:6709 Google Scholar
  53. 53.
    Mulichak AM, LW, Losey HC, Walsh CT, Garavito RM (2004) Biochemistry 43:5170 Google Scholar
  54. 54.
    Mulichak AM, Losey HC, Lu W, Wawrzak Z, Walsh CT, Garavito RM (2003) Proc Natl Acad Sci USA 100:9238 Google Scholar
  55. 55.
    Mulichak AM, Losey HC, Walsh CT, Garavito RM (2001) Structure 9:547 Google Scholar
  56. 56.
    Lu W, Oberthür M, Leimkuhler C, Tao J, Kahne D, Walsh CT (2004) Proc Natl Acad Sci USA 101:4390 Google Scholar
  57. 57.
    Solenberg PJ, Matsushima P, Stack DR, Wilkie SC, Thompson RC, Baltz RH (1997) Chem Biol 4:195 Google Scholar
  58. 58.
    Oberthür M, Leimkuhler C, Kruger RG, Lu W, Walsh CT, Kahne D (2005) J Am Chem Soc 127:10747 Google Scholar
  59. 59.
    Losey HC, Jiang J, Biggins JB, Oberthür M, Ye XY, Dong SD, Kahne D, Thorson JS, Walsh CT (2002) Chem Biol 9:1305 Google Scholar
  60. 60.
    Losey HC, Peczuh MW, Chen Z, Eggert US, Dong SD, Pelczer I, Kahne D, Walsh CT (2001) Biochemistry 40:4745 Google Scholar
  61. 61.
    O'Brien DP, Kirkpatrick PN, O'Brien SW, Staroske T, Spencer JB, Williams DH (2000) J Chem Soc Chem Commun 1:103 Google Scholar
  62. 62.
    Feliu L, Planas M (2005) Int J Pept Res Therap 11:53 Google Scholar
  63. 63.
    Preobrashenskaya MN, Olsufyeva EN (2004) Expert Opin Ther Patents 14:141 Google Scholar
  64. 64.
    Shi Z, Griffin JH (1993) J Am Chem Soc 115:6482 Google Scholar
  65. 65.
    Pavlov AY, Berdnikova TF, Olsufyeva EN, Miroshnikova OV, Filiposyanz ST, Preobrazhenskaya MN, Scottani C, Colombo L, Goldstein BP (1996) J Antibiot 49:149 Google Scholar
  66. 66.
    Miroshnikova OV, Printsevskaya SS, Olsufyeva EN, Pavlov AY, Nilius A, Hensey-Rudloff D, Preobrazhenskaya MN (2000) J Antibiot 53:286 Google Scholar
  67. 67.
    Sundram UN, Griffin JH (1995) J Org Chem 60:1102 Google Scholar
  68. 68.
    Kenny MT, Brackman MA, Dulworth JK (1995) Antimicrob Agents Chemother 39:1589 Google Scholar
  69. 69.
    Goldstein BP, Candiani G, Arain TM (1995) Antimicrob Agents Chemother 39:1580 Google Scholar
  70. 70.
    Nicolaou KC, Hughes R, Cho SY, Winssinger N, Smethurst C, Labischinski H, Endermann R (2000) Angew Chem 112:3981, Angew Chem Int Ed 39:3823 Google Scholar
  71. 71.
    Williams DH, Staroske T (1998) Tetrahadron Lett 39:4917 Google Scholar
  72. 72.
    Rao J, Lahiri J, Isaacs L, Weis RM, Whitesides GM (1998) Science 280:708 Google Scholar
  73. 73.
    Weist S, Bister B, Puk O, Bischoff D, Nicholson G, Stockert S, Wohlleben W, Jung G, Süssmuth RD (2002) Angew Chem 114:3531; Angew Chem Int Ed 40:3383 Google Scholar
  74. 74.
    Bister B, Bischoff D, Nicholson GJ, Stockert S, Wink J, Brunati C, Donadio S, Pelzer S, Wohlleben W, Süssmuth RD (2003) Chem Bio Chem 4:658 Google Scholar
  75. 75.
    Weist S, Kittel C, Bischoff D, Bister B, Pfeifer V, Nicholson GJ, Wohlleben W, Süssmuth RD (2004) J Am Chem Soc 126:5942 Google Scholar
  76. 76.
    Süssmuth RD, Pelzer S, Nicholson GJ, Walk T, Wohlleben W, Jung G (1999) Angew Chem 111:2096, Angew Chem Int Ed 38:1976 Google Scholar
  77. 77.
    Pavlov AY, Lazhko EI, Preobrazhenskaya MN (1996) J Antibiot 50:509 Google Scholar
  78. 78.
    Xu R, Greiveldinger G, Marenus LE, Cooper A, Ellman JA (1999) J Am Chem Soc 121:4898 Google Scholar
  79. 79.
    Alekshun MN (2005) Exp Opin Investig Drugs 14:117 Google Scholar
  80. 80.
    Ge Min, Chen Z, Onishi HR, Kohler J, Silver LL, Kerns R, Fukuzawa S, Thompson C, Kahne D (1999) Science 284:507 Google Scholar
  81. 81.
    Sun B, Chen Z, Eggert US, Shaw SJ, LaTour JV, Kahne D (2001) J Am Chem Soc 123:12722 Google Scholar
  82. 82.
    Chen L, Walker D, Sun B, Hu Y, Walker S, Kahne D (2003) Proc Natl Acad Sci USA 100:5658 Google Scholar
  83. 83.
    Walker S, Chen L, Hu Y, Rew Y, Shin D, Boger DL (2005) Chem Rev 105:449 Google Scholar
  84. 84.
    McCafferty DG, Cudic P, Frankel BA, Barkallah S, Kruger RG, Li W (2002) Biopolymers 66:261 Google Scholar
  85. 85.
    Cavalleri B, Pagani H, Volpe G, Selva E, Parenti F (1984) J Antibiot 37:309 Google Scholar
  86. 86.
    Espersen F (1999) Curr Opin Anti-Infect Invest Drugs 1:78 Google Scholar
  87. 87.
    Cudic P, Behenna DC, Kranz JK, Kruger RG, Wand AJ, Veklich YI, Weisel JW, McCafferty DG (2002) Chem Biol 9:897 Google Scholar
  88. 88.
    Mobarakai N, Quale JM, Landman D (1994) Antimicrob Agents Chemother 38:385 Google Scholar
  89. 89.
    Ristow TA, Noskin GA, Warren JR, Peterson LR (1995) Microb Drug Resist 1:335 Google Scholar
  90. 90.
    Ciabatti R, Kettenring JK, Winters G, Tuan G, Zerilli L, Cavalleri B (1989) J Antibiot 42:254 Google Scholar
  91. 91.
    Kettenring JK, Ciabatti R, Winters G, Tamborini G, Cavalleri B (1989) J Antibiot 42:268 Google Scholar
  92. 92.
    Skelton NJ, Harding MM, Mortishire-Smith RJ, Rahman SK, Williams DH, Rance MJ, Ruddock JC (1991) J Am Chem Soc 113:7522 Google Scholar
  93. 93.
    Higashide E, Hatano K, Shibata M, Nakazawa K (1968) J Antibiot 21:126 Google Scholar
  94. 94.
    Kurz M, Guba W (1996) Biochemistry 35:12570 Google Scholar
  95. 95.
    Lo M-C, Helm JS, Sarngadharan G, Pelczer I, Walker S (2001) J Am Chem Soc 123:8640 Google Scholar
  96. 96.
    Farnet CM, Zazopoulos E, Ecopia SA (2002) WO Patent 0231155 Google Scholar
  97. 97.
    McCafferty DG, Cudic P, Frankel BA, Barkallah S, Kruger RG, Li W (2002) Biopolymers 66:261 Google Scholar
  98. 98.
    Reynolds PE, Somner EA (1990) Drugs Exp Clin Res 16:385 Google Scholar
  99. 99.
    Somner EA, Reynolds PE (1990) Antimicrob Agents Chemother 34:413 Google Scholar
  100. 100.
    Brötz H, Bierbaum G, Leopold K, Reynolds PE, Sahl HG (1998) Antimicrob Agents Chemother 42:154 Google Scholar
  101. 101.
    Brötz H, Josten M, Wiedemann I, Schneider U, Götz F, Bierbaum G, Sahl HG (1998) Mol Microbiol 30:317 Google Scholar
  102. 102.
    Lo M-C, Men H, Branstrom A, Helm J, Yao N, Goldman R, Walker S (2000) J Am Chem Soc 122:3540 Google Scholar
  103. 103.
    Hu YN, Helm JS, Chen L, Ye XY, Walker SJ (2003) J Am Chem Soc 125:8736 Google Scholar
  104. 104.
    Helm JS, Chen L, Walker S (2002) J Am Chem Soc 124:13970 Google Scholar
  105. 105.
    Lo M-C (2000) PhD Thesis, Princeton University Google Scholar
  106. 106.
    Ciabatti R, Cavalleri B (1989) EP Patent 321696 Google Scholar
  107. 107.
    Ciabatti R, Cavalleri B (1992) US Patent 5108988 Google Scholar
  108. 108.
    Ciabatti R, Maffioli S, Checchia A, Romano G, Candiani G, Panzone G (2003) WO Patent 2003076460 Google Scholar
  109. 109.
    Rew Y, Shin D, Hwang I, Boger DL (2004) J Am Chem Soc 126:1041 Google Scholar
  110. 110.
    Ciabatti R, Cavalleri B (1989) EP Patent 337203 Google Scholar
  111. 111.
    Ciabatti R, Cavalleri B (1996) US Patent 5491128 Google Scholar
  112. 112.
    Jiang W, Wanner J, Lee RJ, Bonnaud P-Y, Boger DL (2003) J Am Chem Soc 125:1877 Google Scholar
  113. 113.
    De Voe SE, Kunstman MP (1970) US Patent 3495004 Google Scholar
  114. 114.
    He H, Williamson RT, Shen B, Graziani EI, Yang HY, Sakya SM, Petersen PJ, Carter GT (2002) J Am Chem Soc 124:9729 Google Scholar
  115. 115.
    Singh MP, Petersen PJ, Weiss WJ, Janso JE, Luckman SW, Lenoy EB, Bradford PA, Testa RT, Greenstein M (2003) Antimicrob Agents Chemother 47:62 Google Scholar
  116. 116.
    Ruzin A, Singh G, Severin A, Yang Y, Dushin RG, Sutherland AG, Minnick A, Greenstein M, May MK, Shlaes DM, Bradford PA (2004) Antimicrob Agents Chemother 48:728 Google Scholar
  117. 117.
    Sutherland AG, Bailey AR, Cai P, Dushin RG, Liu M, Lotvin J, Ruppen ME (2004) Tetrahedron Asymm 15:2821 Google Scholar
  118. 118.
    He H, Shen B, Petersen PJ, Weiss WJ, Yang HY, Wang TZ, Dushin RG, Koehn FE, Carter GT (2004) Bioorg Med Chem Lett 14:279 Google Scholar
  119. 119.
    Dushin RG, Wang TZ, Sum PE, He H, Sutherland AG, Ashcroft JS, Graziani EI, Koehn FE, Bradford PA, Petersen PJ, Wheless KL, How D, Torres N, Lenoy EB, Weiss WJ, Lang SA, Projan SJ, Shlaes DM, Mansour TS (2004) J Med Chem 47:3487 Google Scholar
  120. 120.
    He H, Wang TZ, Dushin RG, Feng X, Shen B, Ashcroft JS, Koehn FE, Carter GT (2004) Tetrahedron Lett 45:5889 Google Scholar
  121. 121.
    Sum PE, How D, Torres N, Petersen PJ, Lenoy EB, Weiss WJ, Mansour TS (2003) Bioorg Med Chem Lett 13:1151 Google Scholar
  122. 122.
    Sum PE, How D, Torres N, Petersen PJ, Ashcroft J, Graziani EI, Koehn FE, Mansour TS (2003) Bioorg Med Chem Lett 13:2805 Google Scholar
  123. 123.
    Wang TZ, Wheless KL, Sutherland AG, Dushin RG (2004) Heterocycles 62:131 Google Scholar
  124. 124.
    Umezawa H, Maeda K, Takeuchi T, Okami Y (1966) J Antibiot Ser A 19:200 Google Scholar
  125. 125.
    Umezawa H, Suhara Y, Takita T, Maeda K (1966) J Antibiot Ser A 19:210 Google Scholar
  126. 126.
    Boger DL, Cai H (1999) Angew Chem 111:470, Angew Chem Int Ed 38:448 Google Scholar
  127. 127.
    Galm U, Hager MH, van Lanen SG, Ju J, Thorson JS, Shen B (2005) Chem Rev 105:739 Google Scholar
  128. 128.
    Shen B, Du L, Sanchez C, Edwards DJ, Chen M, Murrell JM (2002) J Nat Prod 65:422 Google Scholar
  129. 129.
    Hecht SM (2000) J Nat Prod 63:158 Google Scholar
  130. 130.
    Burger RM (1998) Chem Rev 98:1153 Google Scholar
  131. 131.
    Umezawa H (1971) Pure Appl Chem 28:665 Google Scholar
  132. 132.
    Takita T, Muraoka Y, Yoshika T, Fujii A, Maeda K, Umezawa H (1972) J Antibiot 25:755 Google Scholar
  133. 133.
    Muraoka Y, Fujii A, Yoshioka T, Takita T, Umezawa H (1977) J Antibiot 30:178 Google Scholar
  134. 134.
    Takita T, Muraoka Y, Nakatani T, Fujii A, Umezawa Y, Naganawa H, Umezawa H (1978) J Antibiot 31:801 Google Scholar
  135. 135.
    Fukuoka T, Muraoka Y, Fujii A, Naganawa H, Takita T, Umezawa H (1980) J Antibiot 33:114 Google Scholar
  136. 136.
    Aoyagi Y, Katano K, Suguna H, Primeau J, Chang LH, Hecht SM (1982) J Am Chem Soc 104:5537 Google Scholar
  137. 137.
    Takita T, Umezawa Y, Saito S, Morishima H, Naganawa H, Umezawa H (1982) Tetrahedron Lett 23:521 Google Scholar
  138. 138.
    Saito S, Umezawa Y, Yoshioka T, Takita T, Umezawa H, Muraoka Y (1983) J Antibiot 36:92 Google Scholar
  139. 139.
    Katano K, An H, Aoyagi Y, Overhand M, Sucheck SJ, Stevens WC Jr, Hess CD, Zhou X, Hecht SM (1998) J Am Chem Soc 120:11285 Google Scholar
  140. 140.
    Boger DL, Honda T (1994) J Am Chem Soc 116:5647 Google Scholar
  141. 141.
    Maeda K, Kosaka H, Yagishita K, Umezawa H (1956) J Antibiot Ser A 9:82 Google Scholar
  142. 142.
    Takita T, Maeda K, Umezawa H (1959) J Antibiot Ser A 12:111 Google Scholar
  143. 143.
    Takita T (1959) J Antibiot Ser A 12:285 Google Scholar
  144. 144.
    Kawaguchi H, Tsukiura H, Tomita K, Konishi M, Saito KI, Kobaru S, Numata KI, Fujisawa KI, Miyaki T, Hatori M, Koshiyama H (1977) J Antibiot 30:779 Google Scholar
  145. 145.
    Konishi M, Saito KI, Numata KI, Tsuno T, Asama K, Tsukiura H, Naito T, Kawaguchi H (1977) J Antibiot 30:789 Google Scholar
  146. 146.
    Du L, Sánchez C, Chen M, Edwards DJ, Shen B (2000) Chem Biol 7:623 Google Scholar
  147. 147.
    Du L, Shen B (1999) Chem Biol 6:507 Google Scholar
  148. 148.
    Du L, Chen M, Sánchez C, Shen B (2000) FEMS Microbiol Lett 189:171 Google Scholar
  149. 149.
    Sugiyama M, Davies J (1994) Gene 151:11 Google Scholar
  150. 150.
    Hecht SM (2002) Eur J Cancer 38:S13 Google Scholar
  151. 151.
    Rishel MJ, Hecht SM (2001) Org Lett 3:2867 Google Scholar
  152. 152.
    Leitheiser CJ, Smith KL, Rishel MJ, Hashimoto S, Konishi K, Thomas CJ, Li C, McCormick MM, Hecht SM (2003) J Am Chem Soc 125:8218 Google Scholar
  153. 153.
    Iitaka Y, Nakamura H, Nakatani T, Muraoka Y, Fujii A, Takita T, Umezawa H (1978) J Antibiot 31:1070 Google Scholar
  154. 154.
    Lehmann TE (2002) J Biol Inorg Chem 7:305 Google Scholar
  155. 155.
    Smolentsev G, Soldatov AV, Wasinger EC, Solomon EI (2004) Inorg Chem 43:1825 Google Scholar
  156. 156.
    Otsuka M, Masuda T, Haupt A, Ohno M, Shiraki T, Sugiura Y, Maeda K (1990) J Am Chem Soc 112:838 Google Scholar
  157. 157.
    Owa T, Haupt A, Otsuka M, Kobayashi S, Tomioka N, Itai A, Ohno M, Shiraki T, Uesugi M, Sugiura Y, Maeda K (1992) Tetrahedron 48:1193 Google Scholar
  158. 158.
    Hecht SM (1995) Cancer chemotherapeutic agents. Am Chem Soc, Washington DC Google Scholar
  159. 159.
    Berry DE, Chang LH, Hecht SM (1985) Biochem 24:3207 Google Scholar
  160. 160.
    Shipley JB, Hecht SM (1988) Chem Res Toxicol 1:25 Google Scholar
  161. 161.
    Carter BC, Murty VS, Reddy KS, Wang SN, Hecht SM (1990) J Biol Chem 265:4193 Google Scholar
  162. 162.
    Nivorozhkin AL, Girerd JJ (1996) Angew Chem 108:665; Angew Chem Int Ed 35:609 Google Scholar
  163. 163.
    Raymond KN, Dertz EA, Kim SS (2003) Proc Natl Acad Sci USA 100:3584 Google Scholar
  164. 164.
    Walsh CT, Liu J, Rusnak F, Sakaitani M (1990) Chem Rev 90:1105 Google Scholar
  165. 165.
    Pollack JR, Neilands JB (1970) Biochem Biophys Res Commun 38:989 Google Scholar
  166. 166.
    O'Brien IG, Gibson F (1970) Biochim Biophys Acta 215:393 Google Scholar
  167. 167.
    Hantke K, Nicholson G, Rabsch W, Winkelmann G (2003) Proc Natl Acad Sci USA 100:3677 Google Scholar
  168. 168.
    Bister B, Bischoff D, Nicholson GJ, Valdebenito M, Schneider K, Winkelmann G, Hantke K, Süssmuth RD (2004) Biometals 17:471 Google Scholar
  169. 169.
    Crosa JH, Walsh CT (2002) Microbiol Mol Biol Rev 66:223 Google Scholar
  170. 170.
    Bäumler AJ, Tsolis RM, van der Velden AW, Stojiljkovic I, Anic S, Heffron F (1996) Gene 183:207 Google Scholar
  171. 171.
    Bäumler AJ, Norris TL, Lasco T, Voigt W, Reissbrodt R, Rabsch W, Heffron F (1998) J Bacteriol 180:1446 Google Scholar
  172. 172.
    Rabsch W, Voigt W, Reissbrodt R, Tsolis RM, Baumler AJ (1999) J Bacteriol 181:3610 Google Scholar
  173. 173.
    Fischbach MA, Lin H, Liu DR, Walsh CT (2005) Proc Natl Acad Sci USA 102:571 Google Scholar
  174. 174.
    Lin H, Fischbach MA, Liu DR, Walsh CT (2005) J Am Chem Soc 127:11075 Google Scholar
  175. 175.
    Zhu M, Valdebenito M, Winkelmann G, Hantke K (2005) Microbiology 151:2363 Google Scholar
  176. 176.
    Bjarnason J, Southward CM, Surette MG (2003) J Bacteriol 185:4973 Google Scholar
  177. 177.
    Konopka K, Neilands JB (1984) Biochemistry 23:2122 Google Scholar
  178. 178.
    Neuhof T, Schmieder P, Preussel K, Dieckmann R, Pham H, Bartl F, von Doehren H (2005) J Nat Prod 68:695 Google Scholar
  179. 179.
    Jolad SD, Hoffman JJ, Torrance SJ, Wiedhopf RM, Cole JR, Arora SK, Bates RB, Gargiulo RL, Kriek GR (1977) J Am Chem Soc 99:8040 Google Scholar
  180. 180.
    Bewley CA, He H, Williams DH, Faulkner DJ (1996) J Am Chem Soc 118:4314 Google Scholar
  181. 181.
    Bewley CA, Holland ND, Faulkner DJ (1996) Experiencia 52:716 Google Scholar
  182. 182.
    McDonald LA, Barbieri LR, Carter GT, Lenoy E, Lotvin J, Petersen PJ, Siegel MM, Singh G, Williamson RT (2002) J Am Chem Soc 124:10260 Google Scholar
  183. 183.
    Lin Y, Li Z, Francisco GD, McDonald LA, Davis RA, Singh G, Yang Y, Mansour TS (2002) Bioorg Med Chem Lett 12:2341 Google Scholar
  184. 184.
    Umezawa H, Kenji M, Tomio T, Yoshiro O (1996) J Antibiot Ser A 19:200 Google Scholar
  185. 185.
    Ichikawa T, Matsuda A, Miyamoto K, Tsubosaki M, Kaihara T, Sakamoto K, Umezawa H (1967) J Antibiot Ser A 20:149 Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2006

Authors and Affiliations

  1. 1.Institut für Chemie/FG Organische ChemieTechnische Universität BerlinBerlinGermany

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