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Synthesis of deuterated vitamin B 6 compounds
Author(s) -
Coburn S. P.,
Lin C. C.,
Schaltenbrand W. E.,
Mahuren J. D.
Publication year - 1982
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.2580190510
Subject(s) - chemistry , pyridoxamine , pyridoxine , pyridoxal , pyridoxal phosphate , hydroxymethyl , deuterium , pyridoxine hydrochloride , nuclear chemistry , phosphate , organic chemistry , biochemistry , cofactor , physics , quantum mechanics , enzyme
3‐Hydroxy‐4‐(hydroxymethyl)‐5‐(hydroxymethyl‐d 2 )‐2‐methylpyridine(pyridoxine‐d 2 ) was prepared by reduction of α 4 ‐3‐0‐isopropylidene‐5‐pyridoxic acid with lithium aluminum deuteride. Deuterium was inserted in the 2‐methyl group using base catalyzed exchange between deuterium oxide and N‐benzyl pyridoxine. Pyridoxine‐d 2 was converted to pyridoxal, pyridoxamine, pyridoxic acid, pyridoxine phosphate, pyridoxal phosphate, and pyridoxamine phosphate. After acetylation the nonphosphorylated forms could be analyzed by gas chromatography‐chemical ionization mass spectroscopy.