Biosynthetic potential of sesquiterpene synthases: alternative products of tobacco 5-epi-aristolochene synthase.
Nicotiana tabacum (tobacco) 5-epi-aristolochene synthase (TEAS) serves as an useful model for understanding the enzyme mechanisms of sesquiterpene biosynthesis. Despite extensive bio-chemical and structural characterization of TEAS, a more detailed analysis of the reaction product spectrum is lacking. This study reports the discovery and quantification of several alternative sesquiterpene products generated by recombinant TEAS in the single-vial GC-MS assay. The combined use of chiral and non-polar stationary phases for gas chromatography separations proved critical for resolving the numerous sesquiterpene products of TEAS for mass spectral analysis and identification. Co-injection studies with available authentic standards from both synthetic and natural sources further corroborated the assignment of several compounds, resulting in an annotated reaction mechanism accounting for their biosynthesis. Moreover, a previously undocumented farnesyl trans-cis isomerization pathway was observed.
21 references, click to expand
-
4S-limonene synthase from the oil glands of spearmint (Mentha spicata). cDNA isolation, characterization, and bacterial expression of the catalytically active monoterpene cyclase.J Biol Chem. 1993 Nov 5;268(31):23016-24 PMID: 8226816
-
Pre-steady-state study of recombinant sesquiterpene cyclases.Biochemistry. 1997 Jul 8;36(27):8340-8 PMID: 9204881
-
Structure of trichodiene synthase from Fusarium sporotrichioides provides mechanistic inferences on the terpene cyclization cascade.Proc Natl Acad Sci U S A. 2001 Nov 20;98(24):13543-8 PMID: 11698643
-
Gene family for an elicitor-induced sesquiterpene cyclase in tobacco.Proc Natl Acad Sci U S A. 1992 Nov 15;89(22):11088-92 PMID: 1438319
-
The biosynthesis of C5-C25 terpenoid compounds.Nat Prod Rep. 1997 Apr;14(2):111-44 PMID: 9149409
-
Germacrene A is a product of the aristolochene synthase-mediated conversion of farnesylpyrophosphate to aristolochene.J Am Chem Soc. 2002 Oct 2;124(39):11636-41 PMID: 12296728
-
Cloning, expression, and characterization of epi-cedrol synthase, a sesquiterpene cyclase from Artemisia annua L.Arch Biochem Biophys. 1999 Sep 15;369(2):213-22 PMID: 10486140
-
Expression of a plant sesquiterpene cyclase gene in Escherichia coli.Arch Biochem Biophys. 1994 Dec;315(2):527-32 PMID: 7986100
-
Cloning of casbene synthase cDNA: evidence for conserved structural features among terpenoid cyclases in plants.Proc Natl Acad Sci U S A. 1994 Aug 30;91(18):8497-501 PMID: 8078910
-
The cyclization of farnesyl diphosphate and nerolidyl diphosphate by a purified recombinant delta-cadinene synthase.Plant Physiol. 2001 Apr;125(4):1754-65 PMID: 11299356
-
Sesquiterpene synthases from grand fir (Abies grandis). Comparison of constitutive and wound-induced activities, and cDNA isolation, characterization, and bacterial expression of delta-selinene synthase and gamma-humulene synthase.J Biol Chem. 1998 Jan 23;273(4):2078-89 PMID: 9442047
-
The variability of sesquiterpenes emitted from two Zea mays cultivars is controlled by allelic variation of two terpene synthase genes encoding stereoselective multiple product enzymes.Plant Cell. 2004 May;16(5):1115-31 PMID: 15075399
-
Total synthesis of taxol.Nature. 1994 Feb 17;367(6464):630-4 PMID: 7906395
-
Cloning and bacterial expression of a sesquiterpene cyclase from Hyoscyamus muticus and its molecular comparison to related terpene cyclases.J Biol Chem. 1995 Mar 31;270(13):7375-81 PMID: 7706281
-
A single-vial analytical and quantitative gas chromatography-mass spectrometry assay for terpene synthases.Anal Biochem. 2004 Dec 15;335(2):210-7 PMID: 15556559
-
Induction of sesquiterpene cyclase and suppression of squalene synthetase activities in plant cell cultures treated with fungal elicitor.Plant Physiol. 1988 Dec;88(4):1291-6 PMID: 16666457
-
Eremophilane sesquiterpenes from capsidiol.J Org Chem. 2004 Oct 29;69(22):7428-35 PMID: 15497966
-
Structural basis for cyclic terpene biosynthesis by tobacco 5-epi-aristolochene synthase.Science. 1997 Sep 19;277(5333):1815-20 PMID: 9295271
-
Isolation and characterization of two germacrene A synthase cDNA clones from chicory.Plant Physiol. 2002 May;129(1):134-44 PMID: 12011345
-
(+)-Germacrene A biosynthesis . The committed step in the biosynthesis of bitter sesquiterpene lactones in chicoryPlant Physiol. 1998 Aug;117(4):1381-92 PMID: 9701594
-
Germacrene C synthase from Lycopersicon esculentum cv. VFNT cherry tomato: cDNA isolation, characterization, and bacterial expression of the multiple product sesquiterpene cyclase.Proc Natl Acad Sci U S A. 1998 Mar 3;95(5):2216-21 PMID: 9482865
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