Chemical studies on tuberactinomycin. XII. Syntheses and antimicrobial activities of [Ala3, Ala4]-, [Ala3]-, and [Ala4]-tuberactinomycin O.
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Total syntheses of [Ala<SUP>3</SUP>, Ala<SUP>4</SUP>]-, [Ala<SUP>3</SUP>]-, and [Ala<SUP>4</SUP>]-tuberactinomycin O corresponding to deoxy analogs of natural antibiotic tuberactinomycin O were achieved for the purpose of elucidation of relationship between chemical structure and biological activity. Cyclization of the pentapeptide intermediates at two different positions was investigated. Minimum inhibitory concentrations of the synthetic analogs against <I>Mycobacterium</I> or <I>Corynebacterium</I> indicated that both hydroxy groups of two serine residues of tuberactinomycins are not required for antibacterial activity, nor participated to drug-resistancy of bacilli. These analogs were found to have the same conformations in solution as those of natural antibiotic from the results of NMR, ORD, and CD measurements.
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- Chemical studies on tuberactinomycin. XII. Syntheses and antimicrobial activities of [Ala3, Ala4]-, [Ala3]-, and [Ala4]-tuberactinomycin O.