Enzymatic synthesis of tryptamine and its halogen derivatives selectively labeled with hydrogen isotopes
Year: 2013
Type: article
Abstract: Nine isotopomers of tryptamine and its halogen derivatives, labeled with deuterium, tritium in side chain, i.e., [( 1R )- 2 H]-, [( 1R )- 3 H]-, 5-F-[( 1R )- 2 H]-, 5-F-[( 1R )- 3 H]-, 5-Br-[( 1R )- 2 H]-, double labeled [( 1R )- 2 H/ 3 H]-, 5-F-[( 1R )- 2 H/ 3 H]-, and ring labeled [4- 2 H]-, and [5- 2 H]-tryptamine, were obtained by enzymatic decarboxylation of l -Trp and its appropriate derivatives in deuteriated or tritiated media, respectively. Intermediates: [5′- 2 H]- l -Trp used for further decarboxylation was synthesized by enzymatic coupling of [5- 2 H]-indole with S -methyl- l -cysteine, and [4′- 2 H]- l -Trp was obtained by isotope exchange 1 H/ 2 H of the authentic l -Trp dissolved in heavy water induced by UV-irradiation. Doubly labeled [( 1R )- 2 H/ 3 H]- and 5-F-[( 1R )- 2 H/ 3 H]-tryptamine were obtain by decarboxylation of l -Trp or [5′-F]- l -Trp carried out in 2 H 3 HO incubation medium.
Authors: Sylwia Dragulska, Marianna Kańska
Institutions: University of Warsaw, Medical University of Warsaw
Language: English
Subfield: Pharmaceutical Science
Domain: Life Sciences
Open Access status: hybrid
Estimated APC paid: $3,790
OpenAlex ID: W2071850701