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Enzymatic synthesis of tryptamine and its halogen derivatives selectively labeled with hydrogen isotopes.

Dragulska S, Kańska M - J Radioanal Nucl Chem (2013)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Warsaw, Pasteur Str. 1, 02-093 Warsaw, Poland.

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.

No MeSH data available.


The stereochemistry of the enzymatic decarboxylation of α-amino acids
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Fig3: The stereochemistry of the enzymatic decarboxylation of α-amino acids

Mentions: Generally, all nine isotopomers of tryptamine and its halogen derivatives were synthesized in course of enzymatic decarboxylation, Fig. 1, of appropriate derivatives of l-tryptophan. For this reaction instead of the enzyme aromatic l-ADDC (EC 4.1.1.28) l-phenylalanine decarboxylase (EC 4.1.1.53) from Streptococcus faecalis [14] (having the similar properties as ADDC) was used. Previous studies [19, 20] has strongly documented that enzymatic decarboxylation of α-l-amino acids undergoes together with the replacement of carboxyl group by solvent proton (deuteron/triton) with retention of configuration at the α-carbon (Fig. 3).Fig. 3


Enzymatic synthesis of tryptamine and its halogen derivatives selectively labeled with hydrogen isotopes.

Dragulska S, Kańska M - J Radioanal Nucl Chem (2013)

The stereochemistry of the enzymatic decarboxylation of α-amino acids
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4514607&req=5

Fig3: The stereochemistry of the enzymatic decarboxylation of α-amino acids
Mentions: Generally, all nine isotopomers of tryptamine and its halogen derivatives were synthesized in course of enzymatic decarboxylation, Fig. 1, of appropriate derivatives of l-tryptophan. For this reaction instead of the enzyme aromatic l-ADDC (EC 4.1.1.28) l-phenylalanine decarboxylase (EC 4.1.1.53) from Streptococcus faecalis [14] (having the similar properties as ADDC) was used. Previous studies [19, 20] has strongly documented that enzymatic decarboxylation of α-l-amino acids undergoes together with the replacement of carboxyl group by solvent proton (deuteron/triton) with retention of configuration at the α-carbon (Fig. 3).Fig. 3

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Warsaw, Pasteur Str. 1, 02-093 Warsaw, Poland.

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.

No MeSH data available.