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The carbamate moiety of the oxazinidinyl ring can maintain the hydrogen-bonding interactions with A309 of ecFabF. The oxazinidinyl ring is however not strictly an isosteric replacement of the enone ring core of platensimycin due to the lack of the C4 methyl group found in the parent compound
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The carbamate moiety of the oxazinidinyl ring can maintain the hydrogen-bonding interactions with A309 of ecFabF. The oxazinidinyl ring is however not strictly an isosteric replacement of the enone ring core of platensimycin due to the lack of the C4 methyl group found in the parent compound.
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The reductive amination was conducted in the polar protic solvent. MeOH; therefore dipole minimization might not play as great a role in product distribution
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The reductive amination was conducted in the polar protic solvent. MeOH; therefore dipole minimization might not play as great a role in product distribution.
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33
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62349087861
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Using the conventional and usual twofold dilution method, the MIC of oxazinidinyl platensimycin 2 for all the strains would be 128μg mL 1 because the determined MIC value of 90 μg mL 1 lies between 64 and 128 μg mL 1
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1.
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34
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33748482185
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Dihydroplatensimycin, an analogue that lacks the enone moiety, is less active than platensimycin. Also, this keto analogue is unstable and forms cyclized products. See
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Dihydroplatensimycin, an analogue that lacks the enone moiety, is less active than platensimycin. Also, this keto analogue is unstable and forms cyclized products. See: S. B. Singh, H. Jayasuriya. J. G. Ondeyka, K. B. Herath, C. Zhang, D. L. Zink, N. N. Tsou, R. G. Ball, A. Basilio, O. Genilloud, M. T. Diez, F. Vicente, F. Pelaez, K. Young, J. Wang, J. Am. Chem. Soc. 2006, 128, 11916-11920:
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Platensimycin methyl ester is also not a potent antibiotic, see
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Platensimycin methyl ester is also not a potent antibiotic, see: S. B. Singh, K. B. Herath, J. Wang, N. Tsou, R. G. Ball, Tetrahedron Lett. 2007, 48, 5429-5433.
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