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Methylation of myocobacillin with dimethyl sulfate and methyl iodide produced respectively mono- and di-methyl derivatives. the products were inactive against fungal spores and erythrocytes. Tyrosine hydroxyl groups only were methylated; in the monomethyl derivative, the hydroxyl of the tyrosine residue in position 6 is methylated, whereas the hydroxyl of the tyrosine in position 4 remains free; both hydroxyl groups are methylated in the dimethyl derivative. The results indicate that the hydroxyl group of the tyrosine residue in position 6 is essential for the biological activity of mycobacillin.

Studies on mycobacillin derivatives. IV. O-methylation of the antibiotic and identification of the active tyrosine residue.