Sequence analysis of polyprenols by 500 MHz 1H-NMR spectroscopy

Tanaka, Yasuyuki; Hirasawa, Hiroshi

doi:10.1016/0009-3084(89)90005-4

Cited by 25 publications

(15 citation statements)

References 9 publications

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“…For data processing and spectrometer control, TOPSPIN version 2.1 was used. The all-trans-configuration of the geranylgeranyl moiety could be deduced from chemical shifts in accordance with previously published data and from selective rotating frame nuclear Overhauser effect correlation spectroscopy experiments (Tanaka et al, 1982;Tanaka and Hirasawa, 1989).…”

Section: Nmr Analysis Of Geranylgeranyl Fatty Acid Esterssupporting

confidence: 78%

Overexpression of an Isoprenyl Diphosphate Synthase in Spruce Leads to Unexpected Terpene Diversion Products That Function in Plant Defense

et al. 2013

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Spruce (Picea spp.) and other conifers employ terpenoid-based oleoresin as part of their defense against herbivores and pathogens. The short-chain isoprenyl diphosphate synthases (IDS) are situated at critical branch points in terpene biosynthesis, producing the precursors of the different terpenoid classes. To determine the role of IDS and to create altered terpene phenotypes for assessing the defensive role of terpenoids, we overexpressed a bifunctional spruce IDS, a geranyl diphosphate and geranylgeranyl diphosphate synthase in white spruce (Picea glauca) saplings. While transcript level (350-fold), enzyme activity level (7-fold), and in planta geranyl diphosphate and geranylgeranyl diphosphate levels (4-to 8-fold) were significantly increased in the needles of transgenic plants, there was no increase in the major monoterpenes and diterpene acids of the resin and no change in primary isoprenoids, such as sterols, chlorophylls, and carotenoids. Instead, large amounts of geranylgeranyl fatty acid esters, known from various gymnosperm and angiosperm plant species, accumulated in needles and were shown to act defensively in reducing the performance of larvae of the nun moth (Lymantria monacha), a conifer pest in Eurasia. These results show the impact of overexpression of an IDS and the defensive role of an unexpected accumulation product of terpenoid biosynthesis with the potential for a broader function in plant protection.

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Section: Nmr Analysis Of Geranylgeranyl Fatty Acid Esterssupporting

confidence: 78%

Overexpression of an Isoprenyl Diphosphate Synthase in Spruce Leads to Unexpected Terpene Diversion Products That Function in Plant Defense

et al. 2013

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“…[12 -16] Moreover, 2D ( 1 H, 13 C) correlation spectra have been applied for sequence analysis of polyprenols. [17] More accurate assignments have yielded many applications including analysis of compounds with a very large number of isoprene units [18 -21] and accurate tracing of biological pathways in dolichols. [22] Worth noting are 3D models of dolichol-19 and dolichyl-19 phosphate, which were based on 2D 1 H-NMR nuclear Overhauser enhancement spectroscopy (NOESY) results and refined by energy minimization with respect to all atoms using the assisted modelling with energy refinements (AMBER) force field, [23] even though the nuclear Overhauser effect (NOE) constraints used in structural calculations were from broad CH 3 and CH 2 signals.…”

Section: Introductionmentioning

confidence: 99%

Complete ¹H and ¹³C signal assignment of prenol‐10 with 3D NMR spectroscopy

Misiak¹,

Koźmiński²,

Kwasiborska³

et al. 2009

Magnetic Reson in Chemistry

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The complete assignment of (1)H and (13)C chemical shifts of natural abundance prenol-10 is reported for the first time. It was achieved using 3D NMR experiments, which were based on random sampling of the evolution time space followed by multidimensional Fourier transform. This approach makes it possible to acquire 3D NMR spectra in a reasonable time and preserves high resolution in indirectly detected dimensions. It is shown that the interpretation of 3D COSY-HMBC and 3D TOCSY-HSQC spectra is crucial in the structural analysis of prenol-10.

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“…Geometric isomers can be identified by the assignment of methyl proton signals in 1 H NMR. Methyl groups on cis-and trans-polyisoprene generally appear at different chemical shifts; cis: 1.76 ppm and trans: 1.64 ppm in benzene-d 6 (12). The α and ω end terminals can be assigned by high-resolution NMR.…”

mentioning

confidence: 99%

The occurrence of geometric polyprenol isomers in the rubber‐producing plant, Eucommia ulmoides oliver

Bamba

Fukusaki

Kajivama

et al. 2001

Lipids

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The chain length and geometric isomerism of polyprenols from Eucommia ulmoides Oliver were analyzed using supercritical fluid chromatography. After intensive effort to establish separation conditions for geometric isomers, a phenyl-bonded silica gel-packed column was found that cleanly separated poly-trans and -cis prenols. The presence of long-chain poly-trans prenols (>9 mers) was confirmed for the first time in plants. Trans isomers were found in the leaf, seed coat, and root, but not in the bark and seed. Poly-trans prenols in this plant may act as intermediates for trans-polyisoprene biosynthesis.

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Sequence analysis of polyprenols by 500 MHz 1H-NMR spectroscopy

Cited by 25 publications

References 9 publications

Overexpression of an Isoprenyl Diphosphate Synthase in Spruce Leads to Unexpected Terpene Diversion Products That Function in Plant Defense

Overexpression of an Isoprenyl Diphosphate Synthase in Spruce Leads to Unexpected Terpene Diversion Products That Function in Plant Defense

Complete ¹H and ¹³C signal assignment of prenol‐10 with 3D NMR spectroscopy

The occurrence of geometric polyprenol isomers in the rubber‐producing plant, Eucommia ulmoides oliver

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Sequence analysis of polyprenols by 500 MHz 1H-NMR spectroscopy

Cited by 25 publications

References 9 publications

Overexpression of an Isoprenyl Diphosphate Synthase in Spruce Leads to Unexpected Terpene Diversion Products That Function in Plant Defense

Overexpression of an Isoprenyl Diphosphate Synthase in Spruce Leads to Unexpected Terpene Diversion Products That Function in Plant Defense

Complete 1H and 13C signal assignment of prenol‐10 with 3D NMR spectroscopy

The occurrence of geometric polyprenol isomers in the rubber‐producing plant, Eucommia ulmoides oliver

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Complete ¹H and ¹³C signal assignment of prenol‐10 with 3D NMR spectroscopy