Bedoukian   RussellIPM   RussellIPM   Piezoelectric Micro-Sprayer


Home
Animal Taxa
Plant Taxa
Semiochemicals
Floral Compounds
Semiochemical Detail
Semiochemicals & Taxa
Synthesis
Control
Invasive spp.
References

Abstract

Guide

Alphascents
Pherobio
InsectScience
E-Econex
Counterpart-Semiochemicals
Print
Email to a Friend
Kindly Donate for The Pherobase

« Previous AbstractIdentifying an unknown compound in flue gas of semiconductor industry - Forensics of a perfluorocarbon    Next Abstract"Enhancing antioxidant, antiproliferation, and free radical scavenging activities in strawberries with essential oils" »

J Am Chem Soc


Title:Biochemistry and molecular genetics of the biosynthesis of the earthy odorant methylisoborneol in Streptomyces coelicolor
Author(s):Wang CM; Cane DE;
Address:"Department of Chemistry, Brown University, Box H, Providence, Rhode Island 02912-9108, USA"
Journal Title:J Am Chem Soc
Year:2008
Volume:20080619
Issue:28
Page Number:8908 - 8909
DOI: 10.1021/ja803639g
ISSN/ISBN:1520-5126 (Electronic) 0002-7863 (Print) 0002-7863 (Linking)
Abstract:"Methylisoborneol (2) is a volatile organic compound produced by a wide variety of Actinomycete soil organisms, myxobacteria, and cyanobacteria. It has an unusually low odor threshold and, together with geosmin, is responsible for the characteristic smell of moist soil as well as unpleasant taste and odor episodes associated with public water supplies and contamination of various foodstuffs, including fish, wine, and beer. Despite considerable interest in detection and remediation of methylisoborneol, the biosynthesis of this methylated monoterpene has been obscure. In Streptomyces coelicolor, the sco7700 and sco7701 genes are shown to correspond to a two-gene operon responsible for methylisoborneol biosynthesis. Both genes have been amplified by PCR and the resulting DNA has been cloned and expressed in Escherichia coli. Incubation of recombinant SCO7701 protein, annotated as a possible C-methyltransferase, with geranyl diphosphate (1) and S-adenosylmethionine gave the previously unknown compound, (E)-2-methylgeranyl diphosphate (3). Incubation of 3 in the presence of Mg2+ with recombinant SCO7700, previously annotated only as a possible metal-binding protein or terpenoid synthase, resulted in the formation of 2-methylisoborneol (2). The steady-state kinetic parameters for both biochemical reactions have been determined. Incubation of geranyl diphosphate and S-adenosylmethionine with a mixture of both SCO7700 and SCO7701 resulted in formation of methylisoborneol (2). Cyclization of 2-methylgeranyl diphosphate (3) to methylisoborneol (2) likely involves the intermediacy of 2-methyllinalyl diphosphate"
Keywords:"Camphanes/*metabolism DNA, Bacterial/genetics Kinetics Odorants Polymerase Chain Reaction Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Streptomyces coelicolor/enzymology/*genetics/*metabolism;"
Notes:"MedlineWang, Chieh-Mei Cane, David E eng R01 GM030301/GM/NIGMS NIH HHS/ R01 GM030301-28/GM/NIGMS NIH HHS/ R01 GM030301-26/GM/NIGMS NIH HHS/ R01 GM030301-29/GM/NIGMS NIH HHS/ R37 GM030301/GM/NIGMS NIH HHS/ R01 GM030301-27/GM/NIGMS NIH HHS/ GM30301/GM/NIGMS NIH HHS/ Research Support, N.I.H., Extramural 2008/06/20 J Am Chem Soc. 2008 Jul 16; 130(28):8908-9. doi: 10.1021/ja803639g. Epub 2008 Jun 19"

 
Back to top
 
Citation: El-Sayed AM 2024. The Pherobase: Database of Pheromones and Semiochemicals. <http://www.pherobase.com>.
© 2003-2024 The Pherobase - Extensive Database of Pheromones and Semiochemicals. Ashraf M. El-Sayed.
Page created on 19-12-2024