N-iodoacetyl-D-glucosamine, an inhibitor of growth and glycoside uptake in Escherichia coli.
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.
D001693:Biological Transport, Active / Q000187:drug effects; D003864:Depression, Chemical; D004926:Escherichia coli / Q000187:drug effects* / Q000254:growth & development; D005690:Galactose / Q000378:metabolism; D005944:Glucosamine / Q000138:chemical synthesis / Q000494:pharmacology*; D005990:Glycerol / Q000378:metabolism; D006027:Glycosides / Q000378:metabolism*; D007461:Iodoacetates / Q000138:chemical synthesis / Q000494:pharmacology*
D006027:Glycosides; D007461:Iodoacetates; D005944:Glucosamine; D005990:Glycerol; D005690:Galactose