Formation of ethylenethiourea from 5,6-dihydro-3H-imidazo[2,1-c]-1,2,4-dithiazole-3-thione by microorganisms and reducing agents.
Microorganisms formed readily ethylenethiourea (ETU) from 5,6-dihydro-3H-imidazo[2,1-c]-1,2,4-dithiazole-3-thione (DIDT), a spontaneous decomposition product of ethylenebisdithiocarbamates. This conversion also takes place after addition of reducing compounds like cysteine, glutathione or ascorbic acid. It consists of two steps: reduction of the S-S bond of DIDT with subsequent release of CS2 to form ETU. DIDT was reduced by NADH in the presence of enzyme extracts from Pseudomonas fluorescens or Asperigillus niger, or by commercial glutathione reductase or lipoamide dehydrogenase. ETU was formed as a result of this enzymatic reduction. The flavin compounds FMN and FAD were also able to promote the reduction of DIDT by NADH.
D001234:Aspergillus niger / Q000378:metabolism; D002246:Carbon Disulfide / Q000032:analysis; D002474:Cell-Free System; D055598:Chemical Phenomena; D002621:Chemistry; D008058:Dihydrolipoamide Dehydrogenase / Q000378:metabolism; D004926:Escherichia coli / Q000378:metabolism; D005182:Flavin-Adenine Dinucleotide; D005980:Glutathione Reductase / Q000378:metabolism; D007093:Imidazoles / Q000378:metabolism*; D010084:Oxidation-Reduction; D011506:Proteins / Q000378:metabolism; D011551:Pseudomonas fluorescens / Q000378:metabolism; D013844:Thiazoles / Q000378:metabolism*; D013871:Thiones / Q000378:metabolism; D013997:Time Factors
D007093:Imidazoles; D011506:Proteins; D013844:Thiazoles; D013871:Thiones; D005182:Flavin-Adenine Dinucleotide; D008058:Dihydrolipoamide Dehydrogenase; D005980:Glutathione Reductase; D002246:Carbon Disulfide