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Synthesis of deuterated 2‐amino‐1‐methyl‐6‐phenyl‐1H‐imidazo[4,5‐b]pyridine (PhIP) and its N ‐hydroxy derivative
Author(s) -
Tanga Mary J.,
Bupp James E.,
Bradford Wallace W.
Publication year - 2001
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.468
Subject(s) - chemistry , pyridine , metabolite , medicinal chemistry , boron trifluoride , derivative (finance) , deuterium , mutagen , stereochemistry , organic chemistry , carcinogen , biochemistry , catalysis , physics , quantum mechanics , financial economics , economics
The syntheses of the deuterium‐labeled food mutagen 2‐amino‐1‐methyl‐6‐phenyl‐1H‐imidazo[4,5‐b]pyridine (PhIP) and its N ‐hydroxy metabolite are described. Unlabeled PhIP is deuterated using a boron trifluoride phosphoric acid complex in one step. Labeled PhIP– 2 H 5 is nitrosated to give nitro‐PhIP, which is then reduced to N ‐hydroxy–PhIP– 2 H 5 . Copyright © 2001 John Wiley & Sons, Ltd.