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The relationship between structure and activity of taurolin

, : The relationship between structure and activity of taurolin. Journal of Applied Bacteriology 48(1): 89-96

Taurolin [Bis(1,1-dioxo-perhydro-1,2,4 thiadiazinyl-4)methane] is an antimicrobial compound formed by the condensation of 2 molecules of tuarine with 3 of formaldehyde. It releases formaldehyde in contact with bacteria. Evidence for TLC, HPLC [high-pressure liquid chromatography] and NMR spectroscopy indicates that taurolin is mostly hydrolyzed in aqueous solution to release 1 molecule of formaldehyde and 2 monomeric molecules (1,1-dioxo-perhydro-1,2,4-thiadiazine and its carbinolamine derivative). A stable equilibrium is established. Antibacterial activity is not entirely due to adsorption of free formaldehyde but also to reaction with a masked (or latent) formaldehyde, as the activity of taurolin is greater than formaldehyde. The monomer is only slightly active by comparison.


PMID: 6989795

DOI: 10.1111/j.1365-2672.1980.tb05210.x

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