Syn stereochemistry of cyclic ether formation in 1,8-cineole biosynthesis catalyzed by recombinant synthase from Salvia officinalis.
Regiospecifically labeled geranyl diphosphates ((2E,6E)-[1,1,8,8,8-(2)H(5)]- and (2E,6Z)-[1,1,9,9,9-(2)H(5)]-GDP) and D(2)O incorporation, in concert with NMR spectrometry, were employed to demonstrate a unique intramolecular syn-facial protonation-cyclization mechanism of action of 1,8-cineole synthase.
Wise
Mitchell L
ML
Institute of Biological Chemistry, Washington State University, Pullman, Washington 99164, USA.
Urbansky
Marek
M
Helms
Gregory L
GL
Coates
Robert M
RM
Croteau
Rodney
R
D019755:Carbon-Carbon Lyases / Q000737:chemistry* / Q000378:metabolism; D002384:Catalysis; D003511:Cyclohexanols / Q000737:chemistry / Q000378:metabolism*; D000077591:Eucalyptol; D039821:Monoterpenes; D019906:Nuclear Magnetic Resonance, Biomolecular; D010940:Plant Proteins / Q000737:chemistry* / Q000378:metabolism; D011994:Recombinant Proteins / Q000737:chemistry / Q000378:metabolism; D027543:Salvia officinalis / Q000201:enzymology*; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry / Q000378:metabolism*
D003511:Cyclohexanols; D039821:Monoterpenes; D010940:Plant Proteins; D011994:Recombinant Proteins; D013729:Terpenes; C019899:1,8-cineole synthetase; D019755:Carbon-Carbon Lyases; D000077591:Eucalyptol