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Stereospecific N‐methylation of the tetrahydroisoquinoline alkaloids isosalsoline and salsolidine by amine N‐methyltransferase A from bovine liver
Author(s) -
Bahnmaier Albert H.,
Woesle Berthold,
Thomas Helmut
Publication year - 1999
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1999)11:2<160::aid-chir13>3.0.co;2-m
Subject(s) - tetrahydroisoquinoline , chemistry , stereospecificity , methylation , enantiomer , amine gas treating , incubation , methyltransferase , stereochemistry , alkaloid , high performance liquid chromatography , biochemistry , chromatography , organic chemistry , dna , catalysis
Stereospecific N‐methylation of the tetrahydroisoquinoline alkaloids isosalsoline (7‐hydroxy‐6‐methoxy‐1‐methyl‐1,2,3,4‐tetrahydroisoquinoline) and salsolidine (6,7‐dimethoxy‐1‐methyl‐1,2,3,4‐tetrahydroisoquinoline) by amine N‐methyltransferase A isolated from bovine liver is reported. Incubation with S‐adenosylmethionine as cosubstrate revealed that in case of isosalsoline, an endogenous tetrahydroisoquinoline alkaloid, the (+)‐(R)‐enantiomer, is preferentially methylated, whereas in the case of salsolidine the (−)‐(S)‐enantiomer is preferentially methylated. The results were obtained by using two independent methods, namely a radioassay and HPLC following separate incubation experiments. Chirality 11:160–165, 1999. © 1999 Wiley‐Liss, Inc.