A Moenomycin-type Structural Analogue of Lipid II Some Possible Mechanisms of the Mode of Action of Transglycosylase Inhibitors can be Discarded

Advanced Synthesis and Catalysis

Volumn 339, Issue 4, 1997, Pages 340-358

  Kosmol, Ralf ^a   Hennig, Lothar ^a   Welzel, Peter ^a   Findeisen, Matthias ^a   Müller, Dietrich ^b   Markus, Astrid ^c   Van Heijenoort, Jean ^d  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b RUHR UNIVERSITY BOCHUM   (Germany)

^c SANOFI   (France)

^d UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2742552031     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (78)

1. For leading references, see Y. Hatanaka, M. Hashimoto, S. Nishihara, H. Narimatsu, Y. Kanaoka, Carbohydr. Res. 294 (1996) 95
2. For leading references, see T. D. H. Bugg, P. E. Brandish, FEMS Microbiology Lett. 119 (1994) 255
3. J. B. Ward, H. R. Perkins, Biochem. J. 135 (1973) 721
4. For leading references, see J.-M. Ghuysen, Annu. Rev. Microbiol. 45 (1991) 37
5. The process is more complicated than summarized here as has brilliantly been unraveled by the Williams group. For leading references, see D. A. Beauregard, D. H. Williams, M. N. Gwynn, D. J. C. Knowles, Antimicrob. Agents Chemother. 39 (1995) 781
6. Y. van Heijenoort, M. Leduc, H. Singer, J. van Heijenoort, J. Gen. Microbiol. 133 (1987) 667
7. For leading references, see P. Welzel: Antibiotics and Antiviral Compounds - Chemical Synthesis and Modification, K. Krohn, H. A. Kirst, H. Maag (eds.), VCH, Weinheim 1993, 373
8. For leading references, see L. Qiao, B. W. Murray, M. Shimazaki, J. Schultz, C.-H. Wong, J. Am. Chem. Soc. 118 (1996) 7653
9. See T. J. Martin, G. Dufner, B. Kratzer, R. R. Schmidt, Glycoconjugate J. 13 (1996) 547
10. a) O. Ritzeler, L. Hennig, M. Findeisen, P. Welzel, D. Müller, Tetrahedron 53 (1997) 1665
11. b) O. Ritzeler, L. Hennig, M. Findeisen, P. Welzel, D. Müller, A. Markus, G. Lemoine, M. Lampilas, J. van Heijenoort, Tetrahedron 53 (1997) 1675
12. c) G. Range, R. Krähmer, P. Welzel, D. Müller, G. F. Herrmann, U. Kragl, Ch. Wandrey, A. Markus, Y. van Heijenoort, J. van Heijenoort, Tetrahedron 53 (1997) 1695
13. For leading references, see R. Berendes, L. Jaenicke, Biol. Chem. Hoppe-Seyler 373 (1992) 35
14. J. Scherkenbeck, A. Hiltmann, K. Hobert, W. Bankova, T. Siegels, M. Kaiser, D. Müller, H. J. Veith, H.-W. Fehlhaber, G. Seibert, A. Markus, M. Limbert, G. Huber, D. Böttger, A. Stärk, S. Takahashi, Y. van Heijenoort, J. van Heijenoort, P. Welzel, Tetrahedron 49 (1993) 3091
15. G. Magnusson, G. Noori, J. Dahmen, T. Frejd, T. Lave, Acta Chem. Scand. Ser. B 35 (1981) 213
16. T. Takano, F. Nakatsubo, K. Murakami, Carbohydr. Res. 203 (1990) 341
17. G. Zemplén, E. Pacsu, Ber. Dtsch. Chem. Ges. 62 (1929) 1613
18. R. Kosmol, Dissertation, Universität Leipzig 1997
19. R. Johansson, B. Samuelsson, J. Chem. Soc., Chem. Commun. 1984, 201; R. Johansson, B. Samuelsson, J. Chem. Soc., Perkin Trans. 1 1984, 2371; see also M. E. Evans, Carbohydr. Res. 21 (1972) 473
20. R. Johansson, B. Samuelsson, J. Chem. Soc., Chem. Commun. 1984, 201; R. Johansson, B. Samuelsson, J. Chem. Soc., Perkin Trans. 1 1984, 2371; see also M. E. Evans, Carbohydr. Res. 21 (1972) 473
21. R. Johansson, B. Samuelsson, J. Chem. Soc., Chem. Commun. 1984, 201; R. Johansson, B. Samuelsson, J. Chem. Soc., Perkin Trans. 1 1984, 2371; see also M. E. Evans, Carbohydr. Res. 21 (1972) 473
22. Review: M. Lalonde, T. H. Chan, Synthesis 1985, 817
23. M. Heuer, K. Hohgardt, F. Heinemann, H. Kühne, W. Dietrich, D. Grzelak, D. Müller, P. Welzel, Tetrahedron 50 (1994) 2029
24. E. J. Corey, A. Venkateswarlu, J. Am. Chem. Soc. 94 (1972) 6190
25. T. Halmos, R. Montserret, J. Filippi, K. Antonakis, Carbohydr. Res. 170 (1987) 57
26. S. S. Bhattacharjee, P. A. J. Gorin, Can. J. Chem. 47 (1969) 1195
27. A. Lipták, J. Imre, J. Harangi, P. Nánási, A. Neszmélyi, Tetrahedron 38 (1982) 3721
28. M. Ek, P. J. Garegg, H. Hultberg, S. Oscarson, J. Carbohydr. Chem. 2 (1983) 305
29. M. J. Kelly, S. M. Roberts, J. Chem. Soc., Perkin Trans. 1 1991, 787
30. D. Joniak, B. Košíková, L. Kosáková, Collect. Czech. Chem. Commun. 43 (1978) 769
31. See ref. [10a] and references therein.
32. A. E. J. de Nooy, A. C. Besemer, H. van Bekkum, Tetrahedron 51 (1995) 8023
33. P. A. Anelli, F. Montanari, S. Quid, Org. Synth. 69 (1990) 212
34. N. J. Davis, S. L. Flitsch, Tetrahedron Lett. 34 (1993) 1181
35. Z. Györgydeák, J. Thiem, Carbohydr. Res. 268 (1995) 85
36. A. E. J. de Nooy, A. C. Besemer, H. van Bekkum, Carbohydr. Res. 269 (1995) 89
37. M. Marx, T. T. Tidwell, J. Org. Chem. 49 (1984) 788
38. Z. Ma, J. M. Bobbitt, J. Org. Chem. 56 (1991) 6110
39. B. S. Bal, W. E. Childers, Jr., H. W. Pinnick, Tetrahedron 37 (1981) 2091
40. H. A. Staab, M. Lüking, F. H. Dürr, Chem. Ber. 95 (1962) 1275; H. A. Staab, Angew. Chem. 74 (1962) 407
41. H. A. Staab, M. Lüking, F. H. Dürr, Chem. Ber. 95 (1962) 1275; H. A. Staab, Angew. Chem. 74 (1962) 407
42. B. Classon, P. J. Garegg, B. Samuelsson, Acta Chem. Scand. Ser. B 38 (1984) 419
43. U. Peters, W. Bankova, P. Welzel, Tetrahedron 43 (1987) 3803
44. G. Blatter, J.-M. Beau, J.-C. Jacquinet, Carbohydr. Res. 260 (1994) 189
45. C. Coutant, J.-C. Jacquinet, J. Chem. Soc., Perkin Trans. 1 1995, 1573
46. F. Dasgupta, L. Anderson, Carbohydr. Res. 202 (1990) 239
47. H. G. Kuivila, Synthesis 1970, 499
48. U. Möller, K. Hobert, A. Donnerstag, P. Wagner, D. Müller, H.-W. Fehlhaber, A. Markus, P. Welzel, Tetrahedron 49 (1993) 1635, and references therein
49. J. Lüning, U. Möller, N. Debski, P. Welzel, Tetrahedron Lett. 34 (1993) 5871
50. K. Nakayama, K. Uoto, K. Higashi, T. Soga, T. Kusama, Chem. Pharm. Bull. 40 (1992) 1718
51. J. Mulzer, B. Schöllhorn, Angew. Chem. 102 (1990) 433; Angew. Chem., Int. Ed. Engl. 29 (1990) 431
52. J. Mulzer, B. Schöllhorn, Angew. Chem. 102 (1990) 433; Angew. Chem., Int. Ed. Engl. 29 (1990) 431
53. J. M. Lassaletta, R. R. Schmidt, Synlett 1995, 925; J. M. Lassaletta, R. R. Schmidt, Liebigs Ann. 1996, 1417; D. Icheln, B. Gehrcke, Y. Piprek, P. Mischnick, W. A. König, M. A. Dessoy, A. F. Morel, Carbohydr. Res. 280 (1996) 237
54. J. M. Lassaletta, R. R. Schmidt, Synlett 1995, 925; J. M. Lassaletta, R. R. Schmidt, Liebigs Ann. 1996, 1417; D. Icheln, B. Gehrcke, Y. Piprek, P. Mischnick, W. A. König, M. A. Dessoy, A. F. Morel, Carbohydr. Res. 280 (1996) 237
55. J. M. Lassaletta, R. R. Schmidt, Synlett 1995, 925; J. M. Lassaletta, R. R. Schmidt, Liebigs Ann. 1996, 1417; D. Icheln, B. Gehrcke, Y. Piprek, P. Mischnick, W. A. König, M. A. Dessoy, A. F. Morel, Carbohydr. Res. 280 (1996) 237
56. H. Hohgardt, W. Dietrich, H. Kühne, D. Müller, D. Grzelak, P. Welzel, Tetrahedron 44 (1988) 5771; J. Lüning, U. Möller, D. Müller, P. Welzel, A. Markus, Y. van Heijenoort, J. van Heijenoort, Tetrahedron 49 (1993) 10587, see also ref. [43]
57. H. Hohgardt, W. Dietrich, H. Kühne, D. Müller, D. Grzelak, P. Welzel, Tetrahedron 44 (1988) 5771; J. Lüning, U. Möller, D. Müller, P. Welzel, A. Markus, Y. van Heijenoort, J. van Heijenoort, Tetrahedron 49 (1993) 10587, see also ref. [43]
58. R. G. K. Schneiderwind-Stöcklein, I. Ugi, Z. Naturforsch. Teil B 39 (1984) 968
59. a) L. Wozniak, J. Kowalski, J. Chojnowski, Tetrahedron Lett. 26 (1985) 4965;
60. b) Y. Hayakawa, M. Uchiyama, R. Noyori, Tetrahedron Lett. 27 (1986) 4191;
61. c) W. P. Jackson, Synlett 1990, 536
62. J. Imai, P. F. Torrence, J. Org. Chem. 46 (1981) 4015
63. K. Schaller, J.-V. Höltje, V. Braun, J. Bacteriol. 152 (1982) 994
64. K. Izaki, M. Matsuhashi, J. L. Strominger, J. Biol. Chem. 243 (1968) 3180
65. a) Y. van Heijenoort, M. Derrien, J. van Heijenoort, FEBS Lett. 89 (1979) 141;
66. b) Y. van Heijenoort, J. van Heijenoort, FEBS Lett. 110 (1980) 241
67. H.-W. Fehlhaber, M. Girg, G. Seibert, K. Hobert, P. Welzel, Y. van Heijenoort, J. van Heijenoort, Tetrahedron 46 (1990) 1557
68. D. Kritchevsky, M. R. Kirk, Arch. Biochem. Biophys. 35 (1952) 346
69. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 43 (1978) 2923
70. th ed., Vol. E21a, p. 17, Georg Thieme, Stuttgart 1995
71. The coupling constants of the protons of the allyl group are similar in all subsequent compounds and will not be reported.
72. Not all signals could be identified, possibly due to superposition.
73. Slightly impure sample, see ref. [16]
74. The E and E' assignments possibly have to be interchanged.
75. F-H signals could not be identified.
76. The spectrum displayed small signals of triphenylphosphine or triphenylphosphine oxide.
77. 1H COSY spectrum.
78. OH,2F = 5.6 Hz) could be detected.