Enantiomeric Purity of Biodegradation Products of Juvenogens by Newly Isolated Soil Bacteria

• Published in: Journal of agricultural and food chemistry 2008-08, Vol.56 (15), p.6604-6608
• Main Authors: Novák, Jaroslav, Tykva, Richard, Wimmer, Zdeněk, Pavlík, Milan, Prouza, Marek, Hlavsová, Klára, Zarevúcka, Marie
• Format: Article
• Language: English
• Subjects: Bacillus (bacteria); Bacillus - metabolism; Bacillus simplex; Bacillussp; biodegradation; Biological and medical sciences; carbamates; Carbamates - chemistry; Carbamates - metabolism; chemical structure; Cyclohexanols - chemistry; Cyclohexanols - metabolism; enantiomeric purity; enantiomers; Environmental Chemistry; Food industries; Fundamental and applied biological sciences. Psychology; Hydrolysis; insect growth regulators; insect hormonogen substances; Juvenile Hormones - chemistry; Juvenile Hormones - metabolism; juvenogen; juvenogens; pesticide residues; soil bacteria; Soil Microbiology; Stereoisomerism
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf800526a

Two bacteria were isolated from sand RQ30, characterized as Bacillus simplex and Bacillus sp. strain 05 (GenBank EU399813 ), and were used as biocatalysts for a hydrolytic assay of stability of the cis or trans isomers of ethyl N-{2-{4-{[2-(butanoyl)oxycyclohexyl]methyl}phenoxy}ethyl}carbamate, which are among insect hormonogen substances (juvenogens). The stability tests were performed using simple modeling under laboratory conditions. The structures of the products were assigned as ethyl (1R,2R)-N-{2-{4-[(2-hydroxycyclohexyl)methyl]phenoxy}ethyl}carbamate and ethyl (1S,2R)-N-{2-{4-[(2-hydroxycyclohexyl)methyl]phenoxy}ethyl}carbamate on the basis of 1H and 13C NMR, IR, and FAB-MS analyses.