Summary
Gram-positive bacteria isolated from deep-sea sediments of the Pacific basin showed considerable antibacterial activity. ABacillus strain, isolated from a sediment sample collected at a depth of 4310 m, was shown to produce 3-amino-3-deoxy-D-glucose, a known antibiotic.
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IR spectrum (film): 3300, 1750, 1665, 1540, 1230, and 1060 cm−1;1H NMR (CDCl3):δ 1.90–2.20 ppm (s, OCOCH 3), 3.90 (ddd, J=10.4, 4.4, 2.0 Hz, H-5β), 4.17 (ddd, 11.1, 3.6, 2.1, H-5α), 4.10 (dd, 12.6, 2.0, H-6βa), 4.08 (dd, 12.3, 2.1, H-6αa), 4.33 (dt, 9.6, 10.0, H-3β), 4.76 (dt, 11.2, 10.6, H-3α), 4.35 (dd, 12.6, 4.4, H-6βb), 4.33 (dd, 12.3, 4.0, H-6αb), 4.91 (dd, 8.4, 10.0, H-2β), 4.91 (dd, 10.0, 10.4, H-4β), 4.94 (dd, 10.6, 11.1, H-4α), 5.00 (dd, 3.6, 11.2, H-2α), 5.61 (brd, 9.6, NH-β), 5.54 (brd, 10.6, NH-α), 5.76 (d, 8.4, H-1β), 6.26 (d, 3.6, H-1α);13C NMR (CDCl3): δ 20.5 ppm (q, OCOCH3, 8C), 22.8 (q, NCOCH3, 2C), 49.3 (d, C-3α), 53.2 (d, C-3β), 61.6 (t, C-6α and β), 67.9 (d, C-4α)*, 68.1 (d, C-4β)*, 68.9 (d, C-2α)*, 70.1 (d, C-2β)*, 70.4 (d, C-5α), 73.4 (d, C-5β), 88.7 (d, C-1α), 91.9 (d, C-1β), 168.7 (s, NCOCH3, 2C), 170.2 (s, OCOCH3, 8C).*Assignments may be interchanged.
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Fusetani, N., Ejima, D., Matsunaga, S. et al. 3-Amino-3-deoxy-D-glucose: an antibiotic produced by a deep-sea bacterium. Experientia 43, 464–465 (1987). https://doi.org/10.1007/BF01940457
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DOI: https://doi.org/10.1007/BF01940457