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• W2031673433 abstract "Juvenile hormone esterase (JHE) catalyses the transesterification of juvenile hormones (JH) in the presence of appropriate alcohols to yield ethyl, propyl or butyl JH esters. Using baculovirus-expressed, recombinant Heliothis virescens JHE or hemolymph from several species, we have produced 200–300 μg of JH III ethyl, n-propyl and n-butyl esters from 1.0 mg JH III incubated in 30% (vv) ethanol, 10% 1-propanol or 5% 1-butanol. Alternatively, highly pure JH ethyl esters were chemically synthesized by treating JH acids with diazoethane. Structures were verified by nuclear magnetic resonance (NMR) and/or gas chromatography-mass spectrometry (GC-MS). The hemolymph of Manduca sexta, Tenebrio molitor, Trichoplusia ni, or Schistocerca americana, or recombinant H. virescens JHE all exhibit the same trend in JH ester hydrolysis rate: methyl = ethyl>n-propyl>n-butyl. In contrast, Blaberus giganteus hemolymph hydrolyses JH methyl esters at a four-fold higher rate than JH ethyl esters, but does not hydrolyse JH n-propyl or n-butyl esters at measurable rates. (2Z,6E)-JH I ethyl ester, a significant by-product of the commonly utilized KCN-catalysed transesterification of (2E,6E)-JH I, is not hydrolysed by M. sexta hemolymph or H. virescens recombinant JHE. (2Z,6E)-JH I ethyl ester and (2Z,6E)-JH I ethyl ester diol are metabolized at only slightly lower rates than the corresponding (2E,6E) isomers by M. sexta juvenile hormone epoxide hydrolase (JHEH) and JH diol phosphotransferase (JHDPT), respectively. (2E,6E)-JH I and (2E,6E)-JH I ethyl ester injected into M. sexta larvae yield the same spectrum of metabolites, as do (2E,6E)-JH I diol and (2E,6E)-JH I ethyl ester diol. (2Z,6E)-JH I ethyl ester, however, is converted only to the diol and diol-phosphate metabolites by M. sexta in vivo." @default.
• W2031673433 created "2016-06-24" @default.
• W2031673433 creator A5069286112 @default.
• W2031673433 date "1997-05-01" @default.
• W2031673433 modified "2023-09-25" @default.
• W2031673433 title "The specificity of juvenile hormone esterase revisited" @default.
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• W2031673433 doi "https://doi.org/10.1016/s0965-1748(97)00008-8" @default.
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