Synthesis of [2,3,3,2′,3′,5′,6′‐2H7]‐L‐tyrosine from phenol‐d6

Kendall, John T.

doi:10.1002/1099-1344(200008)43:9<917::aid-jlcr377>3.3.co;2-x

Cited by 2 publications

(5 citation statements)

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“…Asymmetric hydrogenations using chiral rhodium catalysts have also been used for the synthesis of isotopically labeled amino acids [89,90]. For example, Kendall synthesized a multilabeled dehydrotyrosine derivative 75 in five steps from D 6 -phenol 74, which was then hydrogenated in the presence of a chiral rhodium catalyst (Scheme 11.20) [90].…”

Section: Chemical Asymmetric Methodsmentioning

confidence: 99%

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Synthesis of Isotopically Labeled α‐Amino Acids

Reid

Sutherland

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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Section: Chemical Asymmetric Methodsmentioning

confidence: 99%

“…For example, Kendall synthesized a multilabeled dehydrotyrosine derivative 75 in five steps from D 6 -phenol 74, which was then hydrogenated in the presence of a chiral rhodium catalyst (Scheme 11.20) [90]. This gave 76 in 98% e.e.…”

Section: Chemical Asymmetric Methodsmentioning

confidence: 99%

Synthesis of Isotopically Labeled α‐Amino Acids

Reid

Sutherland

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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“…A soln of phenol-d 6 (1, 1.0 g, 9.99 mmol) in anhyd THF (4 mL) was added dropwise over 1 h under N 2 to a cooled suspension (0 °C) of NaH (350.0 mg, 13.85 mmol) in anhyd THF (3 mL). The mixture was stirred at 0 °C for an additional 10 min, MeI (4.6 g, 32.4 mmol) was added rapidly.…”

Section: 3456-pentadeuteroanisole (2)mentioning

confidence: 99%

“…Commercially available phenol-d 6 (1) was converted into 2,3,4,5,6-pentadeuteroanisole (2) in 90% yield by deprotonation with sodium hydride in tetrahydrofuran at 0 °C followed by quenching with iodomethane. Formylation/ oxidation of 2 with formaldehyde-sulfuric acid-d 2 /2,3-dichloro-5,6-dicyano-1,4-benzoquinone in acetonitrile at 80 °C led to a mixture of 3,4,5,6-tetradeutero-o-anisaldehyde (20% yield) and 2,4,6,7-tetradeutero-p-anisaldehyde (3, 60% yield), which could be easily separated by column chromatography.…”

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confidence: 99%

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trans-Resveratrol-d₄, a Molecular Tracer of the Wild-Type Phytoalexin; Synthesis and Spectroscopic Properties

Gabriele¹,

Benabdelkamel²,

Plastina³

et al. 2008

Synthesis

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S y n t h e s i s o f t r a n s -R e s v e r a t r o l -d 4Abstract: A convenient, six-step synthesis of the so far unknown trans-resveratrol-d 4 , (E)-3¢,4,5¢-trihydroxy-2,3,5,6-tetradeuterostilbene, starting from commercially available phenol-d 6 , with an overall yield of 25%, is described. The final labeled resveratrol was fully characterized by MS, IR, and 1 H and 13 C NMR spectroscopy. The isotopic distribution of the final product, determined by high resolution mass spectrometry, was as follows: d 4 , 96%; d 3 , 4%.Resveratrol (3,4¢,5-trihydroxystilbene) is a polyphenolic phytoalexin found in more than 70 plants and many foods, including grapes, peanuts, berries, and red wine. 1 Resveratrol has recently attracted considerable attention in view of its significant biological activity, which include antioxidant and/or anti-inflammatory activity. 2 Recent data suggest that nutritional intake of resveratrol may contribute to the so-called 'French paradox', that is, the unexpectedly low incidence of coronary heart disease in the Mediterranean population, in spite of a relatively high intake of saturated fats. Resveratrol has been shown to inhibit LDL oxidation and prevent the oxidative stress in general, which results in an anti-aging effect. 2,3 Moreover, resveratrol has been classified as a phytoestrogen, due to its ability to interact to estrogenic receptors, and has been shown to exert antiproliferative and cancer-protective effects. 4Considering the potential beneficial effects on human health of resveratrol, the development of new, reliable, and sensitive techniques for its quantitative determination in foods appears to be of primary importance. One of the most promising methodologies for the highly sensitive quantitative determination of microcomponents in food products is currently represented by stable isotope dilution assay (SIDA). 5 Thus, resveratrol could in principle be detected and quantified in food samples by means of SIDA using, for example, a deuterated derivative such as (E)-3¢,4,5¢-trihydroxy-2,3,5,6-tetradeuterostilbene as internal standard, which, however, to our knowledge, has not been reported in the literature so far. Here we wish to present an easy and convenient synthesis for this derivative, starting from commercially available phenol-d 6 , with an overall yield of 25% over six steps.(E)-3¢,4,5¢-Trihydroxy-2,3,5,6-tetradeuterostilbene (transresveratrol-d 4 , 7) has been prepared according to the convergent synthetic strategy shown in Scheme 1.Commercially available phenol-d 6 (1) was converted into 2,3,4,5,6-pentadeuteroanisole (2) in 90% yield by deprotonation with sodium hydride in tetrahydrofuran at 0 °C followed by quenching with iodomethane. Formylation/ oxidation of 2 with formaldehyde-sulfuric acid-d 2 /2,3-dichloro-5,6-dicyano-1,4-benzoquinone in acetonitrile at 80 °C led to a mixture of 3,4,5,6-tetradeutero-o-anisaldehyde (20% yield) and 2,4,6,7-tetradeutero-p-anisaldehyde (3, 60% yield), which could be easily separated by column chromatography. On the other hand, commerciall...

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Synthesis of [2,3,3,2′,3′,5′,6′‐2H7]‐L‐tyrosine from phenol‐d6

Cited by 2 publications

References 0 publications

Synthesis of Isotopically Labeled α‐Amino Acids

Synthesis of Isotopically Labeled α‐Amino Acids

trans-Resveratrol-d₄, a Molecular Tracer of the Wild-Type Phytoalexin; Synthesis and Spectroscopic Properties

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Synthesis of [2,3,3,2′,3′,5′,6′‐2H7]‐L‐tyrosine from phenol‐d6

Cited by 2 publications

References 0 publications

Synthesis of Isotopically Labeled α‐Amino Acids

Synthesis of Isotopically Labeled α‐Amino Acids

trans-Resveratrol-d4, a Molecular Tracer of the Wild-Type Phytoalexin; Synthesis and Spectroscopic Properties

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trans-Resveratrol-d₄, a Molecular Tracer of the Wild-Type Phytoalexin; Synthesis and Spectroscopic Properties