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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

✍ Scribed by Mary J. Tanga; James E. Bupp; Wallace W. Bradford

Publisher
John Wiley and Sons
Year
2001
Tongue
French
Weight
95 KB
Volume
44
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

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.

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