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Synthesis of deuterium labelled eumelanin (precursor) metabolites
Author(s) -
Pavel Stanislav,
Muskiet Frits A. J.
Publication year - 1983
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580200114
Subject(s) - chemistry , deuterium , carboxylic acid , chemical synthesis , organic chemistry , chromatography , stereochemistry , biochemistry , in vitro , physics , quantum mechanics
Starting from 2,5,6‐trideutero‐3,4‐dihydroxyphenylethylamine, a mixture of 4,7‐dideutero‐5,6‐dihydroxyindole, 4,7‐dideutero‐5‐hydroxy‐6‐trideuteromethoxyindole and 4,7‐dideutero‐6‐hydroxy‐5‐trideuterometho‐ xyindole was prepared. A similar procedure for the preparation of 4,7‐dideutero‐5,6‐dihydroxyindolyl‐2‐carboxylic, 4,7‐dideutero‐5‐hydroxy‐6‐trideuteromethoxyindolyl‐2‐carboxylic and 4,7‐dideutero‐6‐hydroxy‐5‐trideuteromethoxyindolyl‐2‐carboxylic acids from methyl ester of 2,5,6‐ trideutero‐L‐3,4‐dihydroxyphenylalanine is described. The procedures are designed for the production of deuterium labelled internal standards for mass fragmentographic analysis of eumelanin (precursor) metabolites in urine. The methods can also be used for the synthesis of non‐deuterated analogs.