N-Iodoacetyl-d-glucosamine, an inhibitor of growth and glycoside uptake in Escherichia coli |
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| Authors: | P. W. Kent J. P. Ackers R. J. White |
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| Affiliation: | Department of Biochemistry, University of Oxford, Oxford OX1 3QU, U.K. |
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| Abstract: | 1. Synthesis of N-iodoacetyl-d-glucosamine and its N-iodo[1,2-(14)C(2)]acetyl form has been achieved from the tetra-O-acetyl amino sugar and iodoacetic acid in the presence of dicyclohexylcarbodi-imide followed by catalytic deacetylation. 2. N-Iodoacetylglucosamine (up to 0.1mm) linearly inhibits uptake (up to 1min) of methyl alpha-d-glucoside by Escherichia coli ML308 and K12. Uptake of methyl beta-d-thiogalactoside and glycerol is also inhibited. 3. Growth of the organism (strain ML308) on glucose, succinate and glycerol is strongly inhibited by the iodoacetyl compound. The inhibition is relieved by N-acetylglucosamine. 4. The inhibitor has multiple effects, some of which are considered to be intracellular. 5. A separate transport pathway exists for N-acetylglucosamine by means of which the iodoacetyl analogue may enter the cell. |
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