Metabolic products of microorganisms. 239. Bacimethrin isolated from Streptomyces albus identification, derivatives, synthesis and biological properties.
Bacimethrin (1), known as a thiamine antagonist produced by Bacillus megatherium, was isolated from Streptomyces albus and has been further characterized by NMR spectra and acetylation. A new easy three step synthesis for 1 is described. The biological activity of 1, and its mode of action were discussed. There are indications that bacimethrin inhibits the phosphorylation of 4-amino-5-hydroxymethyl-2-methylpyrimidine (Pyr-OH) during thiamine biosynthesis.
Drautz
H
H
Institut für Biologie II, Universität Tübingen, FRG.
Messerer
W
W
Zähner
H
H
Breiding-Mack
S
S
Zeeck
A
A
D000107:Acetylation; D010766:Phosphorylation; D011736:Pyridoxine / Q000037:antagonists & inhibitors; D011743:Pyrimidines / Q000138:chemical synthesis / Q000494:pharmacology*; D013302:Streptomyces / Q000378:metabolism*; D013329:Structure-Activity Relationship; D013831:Thiamine / Q000037:antagonists & inhibitors* / Q000096:biosynthesis
D011743:Pyrimidines; C054356:bacimethrin; D011736:Pyridoxine; D013831:Thiamine