Synthesis of Isotopically Labelled L-Phenylalanine and L-Tyrosine

Raap, J.; Nieuwenhuis, S. A. M.; Creemers, Alain F. L.; Hexspoor, Sander; Kragl, Udo; Lugtenburg, J.

doi:10.1002/(sici)1099-0690(199910)1999:10<2609::aid-ejoc2609>3.0.co;2-p

Cited by 46 publications

(10 citation statements)

References 23 publications

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“…[9] Purification by distillation gave ethyl bromoacetate in quantitative yield (Scheme 1). Triethyl phosphite was added to ethyl bromoacetate, to yield triethyl phosphonoacetate (16) by an Arbusov reaction in quantitative yield after distillation under reduced pressure.…”

Section: Synthesis Of Geranyl Bromide (14)mentioning

confidence: 99%

Synthesis and Spectroscopic Characterization of [1′-14C]Ubiquinone-2, [1′-14C]-5-Demethoxy-5-hydroxyubiquinone-2, and [1′-14C]-5-Demethoxyubiquinone-2

et al. 2002

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Section: Synthesis Of Geranyl Bromide (14)mentioning

confidence: 99%

Synthesis and Spectroscopic Characterization of [1′-14C]Ubiquinone-2, [1′-14C]-5-Demethoxy-5-hydroxyubiquinone-2, and [1′-14C]-5-Demethoxyubiquinone-2

et al. 2002

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“…The use of the [ 15 N]ammonium ion or isotopically labeled a-keto acids for this reaction has led to a general method for the synthesis of a range of isotopically labeled a-amino acids [3][4][5][6]. An early example of this approach developed by Ducrocq et al, involved the preparation of 4-[ 2 H 2 ]L-glutamic acid 1 using glutamate dehydrogenase to carry out the reductive amination and alcohol dehydrogenase to recycle the NAD þ [3].…”

Section: Enzyme-catalyzed 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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“…Treatment of compound X (R = H) with potassium cyanate afforded carbamide 8 , that is refluxed in aqueous HCl to obtain 1-acetylimidazolidine-2,4-dione ( 9 ) [48]. Hydantoin derivative 9 is treated with benzaldehyde via a Knoevenagel reaction followed by hydrolysis of product 10 to afford the corresponding α-keto acid IVa or N -acetyl-2,3-dehydroamino acid derivative Ia [49,50]. …”

Section: Synthesis Of 22 Amino Acidsmentioning

confidence: 99%

“…In this scheme the building blocks have been used that are easily available in all possible stable isotope enriched forms. The final product benzonitrile ( 142 ) is therefore now accessible in all possible isotopomeric forms [49]. …”

Section: Synthesis Of 22 Amino Acidsmentioning

confidence: 99%

“…The compound 142 is treated with methyllithium, followed by acid catalyzed hydrolysis to obtain acetophenone that upon reaction with m -chloroperbenzoic acid in water afforded the product phenyl acetate via Bayer-Villiger oxidation. Phenol ( 147 ) is obtained by hydrolysis of phenyl acetate [49]. Phenol 147 underwent an enzyme catalyzed reaction with serine to give a high yield of tyrosine [36,94].…”

Section: Synthesis Of 22 Amino Acidsmentioning

confidence: 99%

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Access to Any Site Directed Stable Isotope (2H, 13C, 15N, 17O and 18O) in Genetically Encoded Amino Acids

Dawadi

Lugtenburg

2013

Molecules

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Proteins and peptides play a preeminent role in the processes of living cells. The only way to study structure-function relationships of a protein at the atomic level without any perturbation is by using non-invasive isotope sensitive techniques with site-directed stable isotope incorporation at a predetermined amino acid residue in the protein chain. The method can be extended to study the protein chain tagged with stable isotope enriched amino acid residues at any position or combinations of positions in the system. In order to access these studies synthetic methods to prepare any possible isotopologue and isotopomer of the 22 genetically encoded amino acids have to be available. In this paper the synthetic schemes and the stable isotope enriched building blocks that are available via commercially available stable isotope enriched starting materials are described.

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Synthesis of Isotopically Labelled L-Phenylalanine and L-Tyrosine

Cited by 46 publications

References 23 publications

Synthesis and Spectroscopic Characterization of [1′-14C]Ubiquinone-2, [1′-14C]-5-Demethoxy-5-hydroxyubiquinone-2, and [1′-14C]-5-Demethoxyubiquinone-2

Synthesis and Spectroscopic Characterization of [1′-14C]Ubiquinone-2, [1′-14C]-5-Demethoxy-5-hydroxyubiquinone-2, and [1′-14C]-5-Demethoxyubiquinone-2

Synthesis of Isotopically Labeled α‐Amino Acids

Access to Any Site Directed Stable Isotope (2H, 13C, 15N, 17O and 18O) in Genetically Encoded Amino Acids

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