Synthesis of [3′‐<sup>14</sup>C] coenzyme Q<sub>10</sub>

Hamamura, Kimio; Yamatsu, Isao; Minami, Norio; Yamagishi, Yoji; Inai, Yuichi; Kijima, Shizumasa; Nakamura, Tetsuya

doi:10.1002/jlcr.588

Cited by 19 publications

(20 citation statements)

References 11 publications

(12 reference statements)

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“…The ready availability of solanesol ( 3 ) and solanesyl bromide ( 4 )12 made these compounds appealing starting materials for construction of an intermediate-sized polyisoprene scaffold (Scheme 1). Double alkylation of dimethyl malonate with 4 gave 5 in 72% yield.…”

Section: Resultsmentioning

confidence: 99%

A Solanesol-Derived Scaffold for Multimerization of Bioactive Peptides

Alleti

Venkataramanarao

et al. 2010

J. Org. Chem.

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A flexible molecular scaffold bearing varying numbers of terminal alkyne groups was synthesized in five steps from solanesol. R(CO)-MSH(4)-NH 2 ligands, which have a relatively low affinity for binding at the human melanocortin 4 receptor (hMC4R), were prepared by solid phase synthesis and were N-terminally acylated using 6-azidohexanoic acid. Multiple copies of the azide N 3 (CH 2 ) 5 (CO)-MSH(4)-NH 2 were attached to the alkyne-bearing, solanesol-derived molecular scaffold via the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. Control studies showed that the binding affinity of the triazole-containing ligand, CH 3 (CH 2 ) 3 (C 2 N 3 )(CH 2 ) 5 (CO)-MSH(4)-NH 2 , was not significantly diminished relative to the corresponding parental ligand, CH 3 (CO)-MSH(4)-NH 2 . In a competitive binding assay using a Eu-labeled probe based on the superpotent ligand NDP-α-MSH, the monovalent and multivalent constructs appear to bind to hMC4R as monovalent species. In a similar assay using a Eu-labeled probe based on MSH(4), modest increases in binding potency with increased MSH(4) content per scaffold were observed.

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Section: Resultsmentioning

confidence: 99%

A Solanesol-Derived Scaffold for Multimerization of Bioactive Peptides

Alleti

Venkataramanarao

et al. 2010

J. Org. Chem.

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“…In the pharmaceutical industry solanesol is used as an intermediate in the synthesis (both chemically and biotechnologically) of metabolically active quinones such as coenzyme Q10 and vitamin K analogs (Naruta, 1980; Hamamura et al, 2002; Choi et al, 2005; Tian et al, 2010; Athiyaman and Sankaranarayanan, 2014). There is also a growing awareness that solanesol may have useful properties in its own right with reports of anti-bacterial, anti-inflammation, and anti-ulcer activities (Serebryakov and Nigmatov, 1990; Khidyrova and Shakhidoyatov, 2002; Guo et al, 2008; Li and Chase, 2010).…”

Section: Introductionmentioning

confidence: 99%

Environmental and Genetic Factors Associated with Solanesol Accumulation in Potato Leaves

et al. 2016

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Solanesol is a high value 45-carbon, unsaturated, all-trans-nonaprenol isoprenoid. Recently solanesol has received particular attention because of its utility, both in its own right and as a precursor in the production of numerous compounds used in the treatment of disease states. Solanesol is found mainly in solanaceous crops such as potato, tomato, tobacco and pepper where it accumulates in the foliage. There is considerable potential to explore the extraction of solanesol from these sources as a valuable co-product. In this study we have characterized the genetic variation in leaf solanesol content in a biparental, segregating diploid potato population. We demonstrate that potato leaf solanesol content is genetically controlled and identify several quantitative trait loci associated with leaf solanesol content. Transient over-expression of genes from the methylerythritol 4-phosphate (MEP) and mevalonic acid (MVA) pathways, either singly or in combination, resulted in enhanced accumulation of solanesol in leaves of Nicotiana benthamiana, providing insights for genetically engineering the pathway. We also demonstrate that in potato, leaf solanesol content is enhanced by up to six-fold on exposure to moderately elevated temperature and show corresponding changes in expression patterns of MEP and MVA genes. Our combined approaches offer new insights into solanesol accumulation and strategies for developing a bio-refinery approach to potato production.

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“…6 The deuteration of decaprenol was performed by treating ethyl decaprenoate 1 with LiAID 4 , and then deuterium oxide. The 1 H-NMR spectra.…”

Section: Resultsmentioning

confidence: 99%

“…Ethyl decaprenoate (all-trans isomer: 95%) was prepared followed the procedure described previously. 6 3,4,5-Trimethoxybenzoic acid 3 was obtained from Tokyo Kasei Organic Chemicals (Tokyo, Japan). Co Q 10 was supplied by Eisai Co., Ltd. Silica gel for chromatography (Wakogel C-200) and deuterium oxide were purchased from Wako Chemical Industries, Osaka, Japan.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of deuterium‐labelled coenzyme Q₁₀

Hamamura

Yamagishi

Kijima

et al. 2002

Labelled Comp Radiopharmac

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SummaryDeuterium-labelled coenzyme Q 10 ([2-CD 3 -1 0 -CD 2 ]coenzyme Q 10 , coenzyme Q 10 -d 5 ) was synthesized by condensation of 2,3-dimethoxy-[5-CD 3 ]methyl-1, 4-hydroquinone with [1-CD 2 ]decaprenol. Five positions were selected for deuteration as replacement at these positions allowed examination of every step of the synthesis. This examination was carried out by a combination of 1 H-and 13 C-nuclear magnetic spectrometry and mass spectrometry. Further, these positions have been proved to be metabolically stable. This reagent makes simultaneous quantification of the source of coenzyme Q 10 (exogenously supplied or endogenously supplied) possible in biological samples by measurements on gas chromatography-mass spectrometry.

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Synthesis of [3′‐¹⁴C] coenzyme Q₁₀

Cited by 19 publications

References 11 publications

A Solanesol-Derived Scaffold for Multimerization of Bioactive Peptides

A Solanesol-Derived Scaffold for Multimerization of Bioactive Peptides

Environmental and Genetic Factors Associated with Solanesol Accumulation in Potato Leaves

Synthesis of deuterium‐labelled coenzyme Q₁₀

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Synthesis of [3′‐14C] coenzyme Q10

Cited by 19 publications

References 11 publications

A Solanesol-Derived Scaffold for Multimerization of Bioactive Peptides

A Solanesol-Derived Scaffold for Multimerization of Bioactive Peptides

Environmental and Genetic Factors Associated with Solanesol Accumulation in Potato Leaves

Synthesis of deuterium‐labelled coenzyme Q10

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Product

Resources

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Synthesis of [3′‐¹⁴C] coenzyme Q₁₀

Synthesis of deuterium‐labelled coenzyme Q₁₀