Enantiomeric purity of biodegradation products of juvenogens by newly isolated soil bacteria.

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 (1 R,2 R)- N-{2-{4-[(2-hydroxycyclohexyl)methyl]phenoxy}ethyl}carbamate and ethyl (1 S,2 R)- N-{2-{4-[(2-hydroxycyclohexyl)methyl]phenoxy}ethyl}carbamate on the basis of (1)H and (13)C NMR, IR, and FAB-MS analyses.