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Abstract
The liposidomycins are a family of novel lipid-containing nucleoside antibiotics that were recently found in the culture filterate and mycelia of Streptomyces griseosporeus.1 These antibiotics inhibit formation of the lipid intermediate in bacterial peptidoglycan synthesis.1,2 The primary site of action of liposidomycin C was found to be phospho-N-acetylmuramylpentapeptide transferase from E. coli Y-10 in peptidoglycan synthesis.3 The structures of liposidomycins A, B, and C were proposed as 1, 2, and 3, respectively, on the basis of degradation and spectroscopic studies,2,4 but six stereogenic centers in the lipid and diazepinone moieties remain unassigned. The overall structure as well as the diazepinone and 5-aminopentose 2-sulfate components are very unique. The present work reports synthetic studies related to the 5-amino-5-deoxy-P-Driboside 2-sulfate part of the liposidomycins.
Notes
Compound 6: mp 140–145 °C; [α]D −5.8° (c 0.24, CHCl3); 1H NMR (80 MHz, CDCl3) δ 2.98 (brs, 2H), 3.31 (s, 3H), 3.90–4.27 (m, 4H), 4.77 (s, 1H), 7.62–7.90 (m, 4H); 13C NMR (20.1 MHz, DMSO-d6) δ 41.4, 54.3, 73.3, 74.4, 79.0, 108.3, 123.0, 131.5, 134.4, 167.8. Anal. Calcd for C14H15O6N: C, 57.33; H, 5.16; N, 4.78. Found: C, 57.71; H, 5.30; N, 4.89.
Compound 12: mp 117–120 °C; [α]D −32.7° (c 0.60, CHCl3); 1H NMR (80 MHz, CDCl3) δ 3.40 (s, 3H), 3.88 (d, J = 7.0Hz, 2H), 4.23–4.84 (m, 3H), 4.91 and 4.95 (AB, 2H), 5.01 (s, 1H), 7.66–7.94 (m, 4H); 13C NMR (20.1 MHz, DMSO-d6) δ 40.7, 54.7, 81.1, 82.4, 83.5, 95.0, 108.4, 122.8, 123.1, 131.4, 134.2, 134.5, 167.8. Anal. Calcd for C15H15O6N: C, 59.01; H, 4.95; N, 4.59. Found: C, 59.19; H, 5.05; N 4.71.
Compound 14a: [α]D + 18.3° (c 0.30, CHCl3); 1H NMR (300 MHz, CDCl3) δ 2.02 (s, 3H), 3.35 (s, 3H), 3.92 (m, 2H), 4.15 (dd, J = 4.9, 1.2Hz, 1H), 4.49 (m, 1H), 4.55 (s, 2H), 4.85 (d, J = 1.2Hz, 1H), 5.09 (dd, J = 6.4, 4.9Hz, 1H), 7.28 (m, 5H), 7.70–7.88 (m, 4H). Anal. Calcd for C23H23O7N: C, 64.93; H, 5.45; N, 3.29. Found: C, 64.62; H, 5.66; N, 3.38.
Compound 14b: [α]D + 2.8° (c 0.29, CHCl3); 1H NMR (270 MHz, CDCl3) δ 2.07 (s, 3H), 3.32 (s, 3H), 3.94 (m, 2H), 4.22 (m, 1H), 4.28 (m, 1H), 4.41 and 4.55 (ABq, J = 10.8Hz, 2H), 4.80 (s, 1H), 5.20 (d, J = 2.7Hz, 1H), 7.23 (s, 5H) 69–7.85 (m, 4H); 13C NMR (75.2 MHz, CDCl3) δ 20.5, 40.7, 55.1, 73.2, 73.7, 77.8, 80.2, 106.3, 123.3, 127.9, 128.1, 128.4, 132.2, 134.1, 137.5, 168.5, 170.2. Anal. Calcd for C23H23O7N: C, 64.93; H, 5.45; N, 3.29. Found: C, 65.01; H, 5.28; N, 3.40.
Compound 16: [α]D −16.9° (c 0.42, CHCl3); 1H NMR (300 MHz, CDCl3) δ 1.10–1.90 (m, 10H), 2.10 (s, 3H), 3.58 (m, 1H), 3.99 (m, 2H), 4.23–4.30 (m, 2H), 4.42 and 4.54 (ABq, J = 10.7Hz, 2H), 5.09 (s, 1H), 5.21 (d, J = 3.6Hz, 1H); 12–7.21 (m, 5H), 7.69–7.85 (m, 4H); 13C NMR (75.2 MHz, CDCl3) δ 20.6, 23.6, 23.9, 25.4, 30.9, 33.2, 40.6, 73.3, 74.4, 75.1, 80.7, 102.8, 123.4, 127.9, 128.1, 128.4, 132.3, 134.1, 137.7, 168.6, 170.4. Anal. Calcd for C28H31O7N: C, 68.14; H, 6.33; N, 2.84. Found: C, 68.42; H, 6.48; N, 2.98.
Compound 17: 1H NMR (300 MHz, DMSO-d6) δ 3.29 (s, 3H), 3.80–3.94 (m, 2H), 4.11 (m, 2H), 4.30 (d, J = 9.0Hz, 1H), 4.60–4.67 (m, 2H), 5.04 (s, 1H), 7.13–7.27 (m, 5H), 7.94–7.97 (m, 4H), 8.13 (t, J = 6.0Hz, 2H), 8.65 (t, J = 4.5Hz, 1H), 8.94 (d, J = 5.0Hz, 2H).