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Augustyniak, W; Bukowski, J.; Jemielity, Jacek; Kański, R.; Kańska, Marianna

doi:10.1023/a:1006718004872

Cited by 7 publications

(4 citation statements)

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“…14 C]-L-Phe, was obtained by the method described earlier 14,15 and subsequently 14 C-labeled L-Phe (43% yield), and [1-14 C]-PPA (40% yield) were prepared as described above.…”

Section: Resultsmentioning

confidence: 99%

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Enzymatic synthesis of phenylpyruvic acid labeled with deuterium, tritium, and carbon‐14

Skowera

Kańska

2008

Labelled Comp Radiopharmac

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The synthesis of isotopomers of phenylpyruvic acid, PPA, selectively labeled with hydrogen isotopes in the 3‐position of the side‐chain is reported. Three deuterium or tritium labeled isotopomers of L‐phenylalanine, L‐Phe, i.e. [(3S)‐2H]‐L‐, [(3S)‐3H]‐L‐, and doubly labeled [(3S)‐2H/3H]‐L‐Phe were synthesized using the enzyme phenylalanine ammonia lyase (EC 4.3.1.5). In the second step these isotopomers of L‐Phe were converted into [(3S)‐2H], [(3S)‐3H]‐, and [(3S)‐2H/3H]‐isotopomers of PPA using the enzyme L‐phenylalanine dedydrogenase (EC 1.4.1.20). The isotopomer of PPA labeled with 14C in carboxylic group, [1‐14C]‐PPA, was obtained in a two‐step enzymatic reaction using [1‐14C]‐cinnamic acid as the starting substrate. Copyright © 2008 John Wiley & Sons, Ltd.

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“…14 C]-L-Phe, was obtained by the method described earlier 14,15 and subsequently 14 C-labeled L-Phe (43% yield), and [1-14 C]-PPA (40% yield) were prepared as described above.…”

Section: Resultsmentioning

confidence: 99%

“…15 Deuteriated water (99.9% D) was obtained from Aldrich. Tritiated water was purchased from INC Pharmaceutical Inc., Irvine, CA, USA.…”

Section: Experimental Materialsmentioning

confidence: 99%

Enzymatic synthesis of phenylpyruvic acid labeled with deuterium, tritium, and carbon‐14

Skowera

Kańska

2008

Labelled Comp Radiopharmac

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“…The isotopomer [1‐ 14 C]‐ l ‐Phe, 1 , (used as internal radiometric standard) was prepared by the conversion of [1‐ 14 C]‐CH 3 COONa in acetic anhydride, [1‐ 14 C]‐(CH 3 O) 2 O and the followed condensation of the resultant product with an benzaldehyde, PhCHO, leading to [1‐ 14 C]‐cinnamic acid, which was enzymatically converted into 1 , Scheme . The isotopomer [2‐ 14 C]‐ l ‐Phe, 2 , was obtained by the, partly similar, combined chemical and enzymatic methods using [2‐ 14 C]‐malonic acid as a source of label, Scheme . Also, the isotopomers [(3 R )‐ 3 H]‐ l ‐Phe, 3 , Scheme , and [(3 S )‐ 3 H]‐ l ‐Phe, 4 , Scheme , were synthesized by the chemical and enzymatic procedures .…”

Section: Methodsmentioning

confidence: 99%

Kinetic and solvent isotope effects on biotransformation of aromatic amino acids and their derivatives

Kańska

Jemielity

Pająk

et al. 2016

Labelled Comp Radiopharmac

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Aromatic amino acids such as l-phenylalanine, l-tryptophan, 3',4'-dihydroxy-l-phenylalanine (l-DOPA), and their derivatives 3',4'-dihydroxyphenylacelaldehyde (DOPAL) and 3',4'-dihydroxyphenylethanol (DOPET), play an essential role in human metabolic processes. Incorrect or slow biotransformation of these compounds leads to some metabolic dysfunctions and in some cases to some neurodegenerative diseases. Therefore, studies of the biotransformation mechanisms of these metabolites draw biochemists' and medical researchers' attention. This study investigates the mechanisms of biotransformation of the aforementioned compounds using kinetic (KIE) and solvent (SIE) isotope effect methods. The overview presents the results and the numerical values of KIE and SIE methods, obtained in the study of biotransformation of l-phenylalanine, 5'-chloro-l-tryptophan, and l-DOPA, catalyzed by the enzymes from the lyases group (phenylalanine ammonia lyase, tryptophan indole-lyase, and tyrosine decarboxylase). Deuterium KIE was also determined during the deamination of 2'-chloro-l-phenylalanine in the presence of the enzyme l-phenylalanine dehydrogenase, as well as in the conversion of DOPAL into DOPET catalyzed by the enzyme alcohol dehydrogenase. The values of KIE and SIE have been determined using a noncompetitive spectrophotometric and a competitive (combined with internal radioactivity standard) radiometric methods.

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“…25, 26 We used isotopically pure K 13 CN and chloroacetic acid to prepare 50% 13 Clabeled malonic acid as outlined in Scheme 3. 27 The aldehyde 7 was prepared as previously reported 28 and then subjected to a Knoevenagel condensation 29 with the labeled malonic acid to afford the 50% of the 13 C-labelled cinnamate 8*.…”

Section: Synthesis Of Prekinamycin Analogues 1-6mentioning

confidence: 99%

Quinone methide chemistry of prekinamycins: 13C- labeling, spectral global fitting and in vitro studies

Khdour

Skibo

2009

Org. Biomol. Chem.

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In this article, we address the presence of the prekinamycin quinone methide using the techniques of spectral global fitting and the 13C-labeling of the reactive centre. Two-electron reduction of a prekinamycin affords a long-lived quinone methide species that was characterised spectrally. A correlation was made between the calculated DeltaE (kcal/mol) values for quinone methide tautomerisation and cytostatic activity to support the postulate that the quinone methide plays a role in prekinamycin biological activity. We also prepared a stable quinone methide of prekinamycin and studied its solution chemistry directly.

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Cited by 7 publications

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Enzymatic synthesis of phenylpyruvic acid labeled with deuterium, tritium, and carbon‐14

Enzymatic synthesis of phenylpyruvic acid labeled with deuterium, tritium, and carbon‐14

Kinetic and solvent isotope effects on biotransformation of aromatic amino acids and their derivatives

Quinone methide chemistry of prekinamycins: 13C- labeling, spectral global fitting and in vitro studies

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