title: Syntheses of halogen derivatives of L-tryptophan, L-tyrosine and L-phenylalanine labeled with hydrogen isotopes.
abstract: Halogenated, labeled with tritium and doubly with deuterium and tritium, derivatives of L-tryptophan, i.e. 5'-bromo-[2-(3)H]-, 5'-bromo-[2-(2)H/(3)H]-, 5'-fluoro-[2-(3)H]-5'-fluoro-[2-(2)H/(3)H]-, 6'-fluoro-[2-(3)H]-, 6'-fluoro-[2-(2)H/(3)H]-L-tryptophan, as well as, L-tyrosine, i.e. 3'-fluoro-[2-(3)H]-, 3'-fluoro-[2-(2)H/(3)H]-, 3'-chloro-[2-(3)H]-, and 3'-chloro-[2-(2)H/(3)H]-L-tyrosine, and also L-phenylalanine, i.e. 2'-fluoro-[(3S)-(3)H]-, 2'-fluoro-[(3S)-(2)H/(3) H]-, 2'-chloro-[(3S)-(3)H]-, 2'-chloro-[(3S)-(2)H/(3)H]-, 4'-chloro-[(3S)-(3)H]-, and 4'-chloro-[(3S)-(2)H/(3)H]-L-phenylalanine were synthesized using enzymatic methods. Isotopomers of L-tryptophan were synthesized by coupling of halogenated indoles with S-methyl-L-cysteine carried out in deuteriated or tritiated incubation media. Labeled halogenated derivatives of L-tyrosine were obtained by the enzymatically supported exchange between halogenated L-tyrosine and isotopic water. Labeled halogenated isotopologues of L-Phe were synthesized by the enzymatic addition of ammonia to halogenated cinnamic acid. As a source of hydrogen tritiated water (HTO) and heavy water (D2O) with addition of HTO were used.
authors.affiliation: Department of Chemistry, University of Warsaw, 1 Pasteur Str., 02-093, Warsaw, Poland.
authors.forename: Małgorzata
authors.initials: M
authors.lastname: Pająk
authors.affiliation: Department of Chemistry, University of Warsaw, 1 Pasteur Str., 02-093, Warsaw, Poland.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Pałka
authors.affiliation: Department of Chemistry, University of Warsaw, 1 Pasteur Str., 02-093, Warsaw, Poland.
authors.forename: Elżbieta
authors.initials: E
authors.lastname: Winnicka
authors.affiliation: Department of Biochemistry, 2nd Faculty of Medicine, Medical University of Warsaw, 61 Żwirki i Wigury Str., 02-091, Warsaw, Poland.
authors.forename: Marianna
authors.initials: M
authors.lastname: Kańska
mesh_terms: D006219:Halogens / Q000737:chemistry*; D010649:Phenylalanine / Q000031:analogs & derivatives*; D019275:Radiopharmaceuticals / Q000138:chemical synthesis*; D014316:Tritium / Q000737:chemistry*; D014364:Tryptophan / Q000031:analogs & derivatives*; D014443:Tyrosine / Q000031:analogs & derivatives*
chemical_list: D006219:Halogens; D019275:Radiopharmaceuticals; D014316:Tritium; D014443:Tyrosine; D010649:Phenylalanine; D014364:Tryptophan
keywords: L-phenylalanine; L-tryptophan; L-tyrosine; deuterium; enzyme; labeling; tritium