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Identification of alkaloids; The condensation products of biogenic amines with formaldehyde, enzymatically formed from 5‐methyltetrahydrofolic acid
Author(s) -
Lauwers W.,
Leysen J.,
Verhoeven H.,
Laduron P.,
Claeys M.
Publication year - 1975
Publication title -
biomedical mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0306-042X
DOI - 10.1002/bms.1200020105
Subject(s) - chemistry , formaldehyde , chromatography , enzyme , thin layer chromatography , yield (engineering) , condensation , mass spectrometry , thin layer , organic chemistry , layer (electronics) , materials science , physics , metallurgy , thermodynamics
The use of thin‐layer chromatography has demonstrated that incubations of indoleamines with 5‐methyl[ 14 C]tetrahydrofolic acid and an enzyme previously described as an N ‐methyltransferase, do not yield N ω , N 1 or O ‐methylated products. Further elucidation by thin‐layer chromatography, gas chromatography, mass spectrometry and selected ion monitoring enabled us to identify the reaction products as tetrahydroisoquinolines and tetrahydro‐β‐carbolines in mixtures incubated respectively with catecholamines and indoleamines in the presence of 5‐methyl[ 14 C]tetrahydrofolic acid and enzyme. The alkaloids have been shown to originate from a spontaneous condensation of the corresponding amines with formaldehyde, this latter being formed in the first stage of the reaction by enzymatic conversion from 5‐methyltetrahydrofolic acid.