Moenomycin and Related Phosphorus-Containing Antibiotics

  • Gerhard Huber
Part of the Antibiotics book series (ANTIBIOTICS, volume 5 / 1)


The antibiotics of the moenomycin group are produced by various species of streptomycetes as shown in Table 1. They are mostly formed as complexes of very similar components. A survey has been published by Slusarchyk (1971).


Cell Wall Synthesis Cell Wall Biosynthesis Uridine Diphosphate Glyceric Acid Peptidoglycan Synthesis 
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  1. Arai, M., Torikata, A., Enokita, R., Fukatsu, H., Nakayama, R., Yoshida, K.: Pholipomycin, a new member of phosphoglycolipid antibiotics. I. Taxonomy of producing organism and fermentation and isolation of pholipomycin. J. Antibiot. (Tokyo) 30, 1049–1054 (1977 a)Google Scholar
  2. Arai, M., Nakayama, R., Yoshida, K., Takeuchi, M., Teramoto, S., Torikata, A.: Pholipomycin, a new member of phosphoglycolipid antibiotics. II. Physico-chemical properties and comparison with other members of this family of antibiotics. J. Antibiot. (Tokyo) 30, 1055–1059 (1977 b)Google Scholar
  3. Bardone, M.R., Paternoster, M., Coronelli, C.: Teichomycins, new antibiotics from Actinoplanes teichomyceticus nov. sp. II. Extraction and chemical characterization. J. Antibiotics (Tokyo) 31, 170–177 (1978)Google Scholar
  4. Bauer, F., Dost, G.: Moenomycin in animal nutrition. Antimicrobial Agents Chemotherapy 1965, 749–752Google Scholar
  5. Benazet, F., Corsar, C., Julou, L., Mancy, D.: Un nouvel antibiotique à longue durée d’action: le 11837 R.P.. Activité antimicrobienne in vitro, activité sur les infections expérimentales et tolérance chez l’animal, p. 166. Abstracts Intern. Congr. Microbiol. Moscow (1966) Bettinger, G.E., Young, F.E.: Tunicamycin, an inhibitor of Bacillus peptidoglycan synthesis. A new site of inhibition. Biochem. Biophys. Res. Commun. 67, 16–21 (1975)PubMedCrossRefGoogle Scholar
  6. Brana, H., Hubacek, J., König, J.: The effect of actinomycin D and flavomycin on Escherichia coli R+ strains. Folia Microbiol. 18, 257–262 (1973)CrossRefGoogle Scholar
  7. Brockmann, H., May, H.U., Lenk, W., Brockmann, H., Jr.: Die Konstitution des Limocrocins. Chem. Ber. 102, 3217–3223 (1969) Brown, W.E., Seinerowa, V., Chan, W.M., Laskin, A.I., Linnet, P., Strominger, J.L.: Inhibition of cell wall synthesis by the antibiotics diumycin and janiemycin. Ann. N. Y. Acad. Sci. 235, 399–405 (1974)PubMedCrossRefGoogle Scholar
  8. Canonica, L., Corbella, A., Jommi, G., Pellizone, F., Scolastico, C.: The synthesis of flavensomycinic acid. Tetrahedron Lett. 1966, 3031–3034 (1966)CrossRefGoogle Scholar
  9. Dealy, J., Moeller, M.W.: Influence of bambermycins on Salmonella infections and antibiotic resistance in swine. J. Anim. Sci. 42, 1331–1336 (1976)PubMedGoogle Scholar
  10. Dealy, J., Moeller, M.W.: Influence of bambermycins on Salmonella infections and antibiotic resistance in calves. J. Anim. Sci. 44, 734–738 (1977)PubMedGoogle Scholar
  11. Dubost, M., Benazet, F., Julou, L., Pascal, C., Despois, R.: Un nouvel antibiotique à longue durée d’action: Le 11837 R.P.. Méthodes de dosage, teneurs plasmatiques chez l’animal et fixation sur les protéines sériques, p. 175. Abstr. Int. Congr. Microbiol. Moscow (1966)Google Scholar
  12. Federic, F., Sokol, A.: Dynamics of the decline of plasmids in Escherichia coli isolated from pig weanlings fed flavomycin as a feed additive. 8. Int. Congr. Chemother., Athen (1973)Google Scholar
  13. Gause, G.F., Kidrina, E.S., Ukhokina, R.S., Gavrilina, G.V.: New antibiotic reistomycin produced by Proactinomyces fructiferi, var. ristomycini. Antibiotiki 8, 387–392 (1963)Google Scholar
  14. Grieco, P.A., Masaki, Y., Boxler, D.: Sesterpenes. I. Stereospecific total synthesis of moenocinol. J. Am. Chem. Soc. 97, 1597–1599 (1975 a)CrossRefGoogle Scholar
  15. Grieco, P.A., Masaki, Y., Boxler, D.: The total synthesis of (±)-diumycinol. J. Org. Chem. 40, 2261–2263 (1975 b)PubMedCrossRefGoogle Scholar
  16. Hammes, W.P., Neuhaus, F.C.: On the mechanism of action of vancomycin: Inhibition of peptidoglycan synthesis in Gaffkya komari. Antimicrob. Agents Chemother. 6, 722–728 (1974)PubMedGoogle Scholar
  17. Heijenoort, Y. van, Derrien, M., Heijenoort, J. van: Polymerization by transglycosylation in the biosynthesis of the peptidoglycan of Escherichia coli K 12 and its inhibition by antibiotics. FEBS Lett. 89, 141–144 (1978)PubMedCrossRefGoogle Scholar
  18. Hentschel, G.: Der Einfluß von Flavomycin auf experimentelle Infektionen der Maus, pp. 82–86. Flavomycin-Symp., Rottach-Egern (1969) Hoechst AG: DBP 1 113 791 (1960)Google Scholar
  19. Huber, G.: Moenomycin. IV. Säurehydrolyse und Charakterisierung der Spaltprodukte. Liebigs Ann. Chem. 707, 170–176 (1967)CrossRefGoogle Scholar
  20. Huber, G.: Phosphoglycerate, a building block of moenomycin. J. Antibiot. 25, 226–229 (1972)PubMedGoogle Scholar
  21. Huber, G., Nesemann, G.: Moenomycin, an inhibitor of cell wall synthesis. Biochem. Biophys. Res. Commun. 30, 7–13 (1968)PubMedCrossRefGoogle Scholar
  22. Huber, G., Schacht, U., Weidenmüller, H.L., Schmidt-Thomé, J., Duphorn, I., Tschesche, R.: Moenomycin, a new antibiotic. II. Characterization and chemistry. Antimicrob. Agents Chemother. 1965, 737–742Google Scholar
  23. Iyobe, S., Mitsuhashi, S., Umezawa, H.: Relationship between sex-pili formation and macarbomycin sensitivity in Escherichia coli. J. Bacteriol. 108, 946–947 (1971)Google Scholar
  24. Izaki, K., Matsuhashi, M., Strominger, J.L.: Glycopeptide transpeptidase and D-alanine carboxypeptidase: penicillin-sensitive enzymatic reactions. Proc. Natl. Acad. Sci. USA 55, 656–663 (1966)PubMedCrossRefGoogle Scholar
  25. Jordan, D.C.: Ristocetin. In: Antibiotics. Mechanism of action. Gottlieb, D., Shaw, P.D. (eds.), Vol. I, pp. 84–89. Berlin, Heidelberg, New York: Springer 1967Google Scholar
  26. Kahan, F.M., Kahan, J.S., Cassidy, P.S., Kropp, H.: The mechanism of action of fosfomycin (phosphonomycin). Ann. N.Y. Acad. Sci. 235, 364–386 (1974)PubMedCrossRefGoogle Scholar
  27. Kirschbaum, J.: Molecular association of the antibiotic prasinomycin. J. Pharm. Sci. 57, 690–692 (1968)PubMedCrossRefGoogle Scholar
  28. Kirschbaum, J., Aszalos, A., Weisenborn, F.L., Coy, N.H.: Aggregates of antibiotics. Stabilities, modes of binding, and methods of disruption of the aggregates of saramycetin and prasinomycin. J. Colloid Interface Sci. 33, 439–444 (1970 a)PubMedCrossRefGoogle Scholar
  29. Kirschbaum, J., Slusarchyk, W.A., Weisenborn, F.L.: Intermolecular bonding of the antibiotic diumycin. J. Pharm. Sci. 59, 749–751 (1970 b) Kuo, S.-C., Lampen, J.O.: Tunicamycin — an inhibitor of yeast glycoprotein synthesis. Biochem. Biophys. Res. Commun. 58, 287–295 (1974)PubMedCrossRefGoogle Scholar
  30. Langenfeld, N., Welzel, P.: D-Moenuronsäure (4-C-Methyl-D-Glucuronsäure), ein neuer Baustein des Antibiotikums Moenomycin A. Tetrahedron letters 1978, 1833–1836Google Scholar
  31. Laskin, A.I., May Chan, W.: The effects of prasinomycin and diumycin on some parameters related to cell wall biosynthesis. Proc. Antimicrob. Anticancer Chemother. I, 233–225 (1970)Google Scholar
  32. Laskin, A.I., May Chan, W., Smith, D.A., Meyers, E.: Mode ofaction of prasinomycin. Antimicrob. Agents Chemother. 1967, 251–256Google Scholar
  33. Lebek, G.: Die Wirkung von Flavomycin auf episomal resistente Keime. Zentralbl. Vet. Med. B 19, 532–539 (1972)Google Scholar
  34. Lenoir, D., Tschesche, R., Wucherpfennig, W., Huber, G., Weidenmüller, H.L.: Moenomycin A. Further characterization and chemistry. Antimicrob. Agents Chemother. 1969, 144–147Google Scholar
  35. Lepetit, S.p.A.: DOS 2608216 (1976)Google Scholar
  36. Linnett, P.E., Strominger, J.L.: Additional antibiotic inhibitors of peptidoglycan synthesis. Antimicrob. Agents Chemother. 4, 231–236 (1973)PubMedGoogle Scholar
  37. Lugtenberg, E.J.J., van Schijndel-Dam, A., van Bellegem, T.H.M.: In vivo and in vitro action of new antibiotics interfering with the utilization of N-acetylglucosamine-N-acetyl-muramylpentapeptide. J. Bacteriol. 108, 20–29 (1971)PubMedGoogle Scholar
  38. Lugtenberg, E.J.J., Hellings, J.A., van de Berg, G.J.: Inhibition of peptidoglycan synthesis by the antibiotic diumycin A. Antimicrob. Agents Chemother. 2, 485–491 (1972)PubMedGoogle Scholar
  39. Mancy, D., Ninet, L., Preud’homme, J., Charpentie, J., Renaut, J., Vuillemin, B.: Un nouvel antibiotique à longue durée d’action. Le 11837 R.P.. Preparation et proprietés physicochimiques, p. 165. Abstr. Int. Congr. Microbiol. Moscow (1966)Google Scholar
  40. Merck Co.: US. Pat. 3 891754 (1973)Google Scholar
  41. Merck Co.: US. Pat. 3 891753 (1974)Google Scholar
  42. Meyers, E., Miraglia, G.J., Smith, D.A., Basch, H.I., Pansy, F.E., Trejo, W.H., Donovick, R.: Biological characterization of prasinomycin, a phosphorus-containing antibiotic. Appl. Microbiol. 16, 603–608 (1968)PubMedGoogle Scholar
  43. Meyers, E., Smith Slusarchyk, D., Bouchard, J.L., Weisenborn, F.L.: The diumycins. New members of an antibiotic family having prolonged in vivo activity. J. Antibiot. 22, 490–493 (1969)Google Scholar
  44. Meyers, E.F., Weisenborn, L., Pansy, F.E., Slusarchyk, D.S., von Saltza, M.H., Rathnum, M.L., Parker, W.L.: Janiemycin, a new peptide antibiotic. J. Antibiot. 23, 502–507 (1970)PubMedGoogle Scholar
  45. Meyers, E., Smith Slusarchyk, D., Pansy, F.E., Basch, H.I., Trejo, W.H., DeBaecke, P.J.: Biological characterization of diumycin, a phosphorus-containing glycolipid antibiotic. J. Antibiot. 25, 163–170 (1972)PubMedGoogle Scholar
  46. Mitsuhashi, S., Iyobe, S., Hashimoto, H., Umezawa, H.: Preferential inhibition of the growth of Escherichia coli strains carrying episomes. J. Antibiot. 23, 319–323 (1970)PubMedGoogle Scholar
  47. Neuhaus, F.C.: D-Cycloserine and D-carbamyl-D-serine. In: Antibiotics. Mechanism of action. Gottlieb, D., Shaw, P.D. (eds.), Vol.1, pp. 40–83. Berlin, Heidelberg, New York: Springer 1967Google Scholar
  48. Nieto, M., Perkins, H.R.: Modifications of the acyl-D-alanyl-D-alanine terminus affecting complex-formation with vancomycin. Biochem. J. 123, 789–803 (1971)PubMedGoogle Scholar
  49. Osborn, M.J.: Personal communication (1971). In: Brown et al. (1974)Google Scholar
  50. Parenti, F., Beretta, G., Berti, M., Arioli, V.: Teichomycins, new antibiotics from Actinoplanes teichomyceticus nov sp. I. Description of the producer strain, fermentation studies and biological properties. J. Antibiot. 31, 276–283 (1978)PubMedGoogle Scholar
  51. Park, J.T.: Uridine-5′-pyrophosphate derivatives. I. Isolation from Staphylococcus aureus. J. Biol. Chem. 194, 885–897 (1952)PubMedGoogle Scholar
  52. Perkins, H.R.: Specificity of combination between mucopeptide precursors and vancomycin or ristocetin. Biochem. J. 111, 195–205 (1969)PubMedGoogle Scholar
  53. Reynolds, P.E.: Studies in the mode of action of vancomycin. Biochim. Biophys. Acta 52, 403–405 (1961)PubMedCrossRefGoogle Scholar
  54. Rhône-Poulenc: FR. Pat. 1428474 (1963)Google Scholar
  55. Rhône-Poulenc: FR. Pat. 1468671 (1964)Google Scholar
  56. Rhône-Poulenc: FR. Pat. 1547388 (1967)Google Scholar
  57. Sambeth, W., Nesemann, G., Bauer, F., Dost, G.: Ausscheidungs- und Rückstandsuntersuchungen mit Flavomycin, p. 133–143. Flavomycin-Symp. Rottach-Egern (1969)Google Scholar
  58. Sandermann, H., Jr.: Moenomycin, An inhibitor of C55-isoprenoid-alcohol kinase from Staphylococcus aureus. Biochim. Biophys. Acta 444, 783–788 (1976)CrossRefGoogle Scholar
  59. Sankyo Co.: DOS 2431270 (1974)Google Scholar
  60. Sattler, A., Kreuzig, F.: The diumycin complex. Comparative studies on antibiotics from diumycin and macarbomycin fermentations. J. Antibiot. 28, 200–204 (1975)PubMedGoogle Scholar
  61. Schacht, U., Huber, G.: Moenomycin. VII. Isolation and properties of further components of the antibiotic moenomycin. J. Antibiot. 22, 597–602 (1969)PubMedGoogle Scholar
  62. Schröder, K., Zeeck, A.: Manumycin. Tetrahedron Lett. 1973, 4995–4998Google Scholar
  63. Siewert, G., Strominger, J.L.: Bacitracin, an inhibitor of the dephosphorylation of lipidpyrophosphate, an intermediate in biosynthesis of the peptidoglycan of bacterial cell walls. Proc. Natl. Acad. Sci. USA 57, 767–773 (1967)PubMedCrossRefGoogle Scholar
  64. Slusarchyk, W.A.: Chemical and biological aspects of a new family of phosphorus-containing antibiotics. Biotechnol. Bioeng. 13, 399–407 (1971)PubMedCrossRefGoogle Scholar
  65. Slusarchyk, W.A., Weisenborn, F.L.: The structure of the lipid portion of the antibiotic prasinomycin. Tetrahedron Lett. 1969, 659–662Google Scholar
  66. Slusarchyk, W.A., Bouchard-Ewing, J.L., Weisenborn, F.L.: Diumycin A’ and Diumycin B’, new members of the diumycin family of antibiotics. J. Antibiot. 26, 391–393 (1973 a)PubMedGoogle Scholar
  67. Slusarchyk, W.A., Osband, J.A., Weisenborn, F.L.: Structure of a novel lipid from the antibiotic diumycin. (a) J. Am. Chem. Soc. 92, 4486–4488 (1970) (b) Tetrahedron 29, 1465–1472 (1973 b)PubMedCrossRefGoogle Scholar
  68. Sokol, A., Federic, F.: Influence of colicinogenic strain given perorally on the occurence of various plasmids of E. coli in piglets fed by flavomycin. Colloquium on R-factors, Smolenice (1974)Google Scholar
  69. Sokol, A., Federic, F., Janouskova, J., Rejtar, V., Krcmery, V.: Hemmwirkung des in nutritiven Konzentrationen verwendeten Flavomycins auf das Vorkommen von R-Faktoren bei Escherichia coli, isoliert aus abgesetzten Ferkeln. Symposium über Fremdstoffe in Nahrungsmitteln. Tatranska Lomnica (1972)Google Scholar
  70. Squibb Sons: US. Pat. 3493653 (1965)Google Scholar
  71. Suzuki, J., Hori, M., Saeki, T., Umezawa, H.: Macarbomycin, an inhibitor of peptidoglycan synthesis. J. Antibiot. 25, 94–104 (1972)PubMedGoogle Scholar
  72. Takahashi, S., Okanishi, A., Utahara, R., Nitta, K., Maeda, K., Umezawa, H.: Macarbomycin, a new antibiotic containing phosphorus. J. Antibiot. 23, 48–50 (1970)PubMedGoogle Scholar
  73. Takahashi, S., Miyamoto, M., Fukatsu, S., Maeda, K., Umezawa, H.: Four minor antibiotics from macarbomycins. J. Antibiot. 26, 542–544 (1973 a)PubMedGoogle Scholar
  74. Takahashi, S., Nitta, K., Honio, S., Cho, F., Umezawa, H.: Biological properties of macarbomycin, an antibiotic containing phosphorus. J. Antibiot. 26, 513–520 (1973 b)PubMedGoogle Scholar
  75. Takatsuki, A., Arima, K., Tamara, G.: Tunicamycin, a new antibiotic. I. Isolation and characterization of tunicamycin. J. Antibiot. 24, 215–223 (1971)PubMedGoogle Scholar
  76. Tamura, G., Sasaki, T., Matsuhashi, M., Takatsuki, A., Yamasaki, M.: Tunicamycin inhibits the formation of lipid intermediate in cell-free peptidoglycan synthesis of bacteria. Agric. Biol. Chem. 40, 447–449 (1976)CrossRefGoogle Scholar
  77. Tanaka, H., Iwai, Y., Oiwa, R., Shinohara, S., Shimizu, S., Oka, T., Omura, S.: Studies on bacterial cell wall inhibitors. II. Inhibition of peptidoglycan synthesis in vivo and in vitro by amphomycin. Biochem. Biophys. Acta 497, 633–640 (1977)PubMedCrossRefGoogle Scholar
  78. Tipper, D.J., Strominger, J.L.: Mechanism of action of penicillins: a proposal based on their structural similarity to acyl-D-alanyl-D-alanine. Proc. Natl. Acad. Sci. USA 54, 1133–1141 (1965)PubMedCrossRefGoogle Scholar
  79. Tkacz, J.S., Lampen, J.O.: Tunicamycin inhibition of polyisoprenyl N-acetylglucosaminyl pyrophosphate formation in calf-liver microsomes. Biochem. Biophys. Res. Commun. 65, 248–257 (1975)PubMedCrossRefGoogle Scholar
  80. Torikata, A., Yoshikawa, H., Katayama, T., Arai, M., Nakahara, M., Kitano, N.: Pholipomycin, a new member of phosphoglycolipid antibiotics. III. Biological properties. J. Antibiot. 30, 1060–1063 (1977)PubMedGoogle Scholar
  81. Tschesche, R., Reden, J.: Synthese des Moenocinols, des Lipoidteils von Moenomycin. Liebigs Ann. Chem. 1974, 853–863Google Scholar
  82. Tschesche, R., Brock, F.X., Duphorn, I.: Über den Lipoidteil Moenocinol des Antibiotikums Moenomycin. Tetrahedron Lett. 1968a, 2905–2909Google Scholar
  83. Tschesche, R., Brock, F.X., Duphorn, I.: Moenomycin. V. Strukturaufklärung des Lipoidteils von Moenomycin. Liebigs Ann. Chem. 720, 58–70 (1968 b)CrossRefGoogle Scholar
  84. Tschesche, R., Lenoir, D., Weidenmüller, H.L.: Über die Struktur des “Chromophors” im Antibiotikum Moenomycin. Tetrahedron Lett. 1969, 141–144Google Scholar
  85. Tschesche, R., Blumbach, J., Welzel, P.: Untersuchungen an 2–Acylamino-Derivaten des Dimedons und des 1,3-Cyclopentandions. Liebigs Ann. Chem. 1973, 407–418Google Scholar
  86. Tsuchiya, K., Takeuchi, Y.: Enduracidin, an inhibitor of cell wall synthesis. J. Antibiot. 21, 426–428 (1968)PubMedGoogle Scholar
  87. Wallhäusser, K.H., Nesemann, G., Präve, P., Steigler, A.: Moenomycin, a new antibiotic. I. Fermentation and isolation. Antimicrob. Agents Chemother. 1965, 734–736Google Scholar
  88. Wasielewski, E. von, Muschaweck, R., Schütze, E.: Moenomycin, a new antibiotic. III. Biological properties. Antimicrob. Agents Chemother. 1965, 743–748Google Scholar
  89. Watanabe, T., Ogata, J., Sugawara, K., Oda, K.: Increase of flavomycin sensitivity of bacteria by R-factors. Proc. First Intern. Sympos. Infect. Antibiot. Resist. Smolenice (1971)Google Scholar
  90. Weisenborn, F.L., Bouchard, J.L., Smith, D., Pansy, F., Maestrone, G., Miraglia, G., Meyers, E.: The prasinomycins. Antibiotics containing phosphorus. Nature (London) 213, 1092–1094 (1967)CrossRefGoogle Scholar
  91. Welzel, P., Buhlke, H., Michalke, P., Simons, J., Winterfeld, L., Tschesche, R., Fehlhaber, H.W., Huber, G.: Zur Struktur eines 2-Aminocyclopentandion-l,3, Galakturonsäure und Chinovosamin enthaltenden Hydrolysenbruchstückes des Antibiotikums Moenomycin A. Tetrahedron Lett. 1973, 227–230Google Scholar
  92. Welzel, P., Witteler, F.J., Müller, D.: Die Verknüpfung von Moenocinol, Glycerinsäure und Phosphorsäure im Antibiotikum Moenomycin A. Tetrahedron Lett. 1976, 1665–1668Google Scholar
  93. Welzel, P., Knupp, G., Witteler, F.J., Schubert, Th., Duddeck, H., Müller, D., Höfle, G.: Unpublished results (1978 a)Google Scholar
  94. Welzel, P., Witteler, F.J., Riemer, W.: Unpublished results (1978 b)Google Scholar
  95. Welzel, P., Witteler, F.J., Duddeck, H., Höfle, G., Riemer, W., Budzikiewicz, H.: Unpublished results (1978 c)Google Scholar
  96. Wise, E.M., Park, J.T.: Penicillin: its basic site of action as an inhibitor of a peptide crosslinking reaction in cell wall mucopeptide synthesis. Proc. Natl. Acad. Sci. USA 54, 75–81 (1965)PubMedCrossRefGoogle Scholar
  97. Wucherpfennig, W.: Über die Struktur des Z1 im Antibiotikum Moenomycin. Diplomarbeit Universität Bonn, Germany (1969)Google Scholar

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  • Gerhard Huber

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