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

J Agric Food Chem. 2008 Aug 13;56(15):6604-8. doi: 10.1021/jf800526a. Epub 2008 Jul 3.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacillus / metabolism*
  • Carbamates / chemistry
  • Carbamates / metabolism
  • Cyclohexanols / chemistry
  • Cyclohexanols / metabolism
  • Hydrolysis
  • Juvenile Hormones / chemistry*
  • Juvenile Hormones / metabolism*
  • Soil Microbiology*
  • Stereoisomerism

Substances

  • Carbamates
  • Cyclohexanols
  • Juvenile Hormones