Synthesis of deuterated 2-amino-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine (PhIP) and its N-hydroxy derivative

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–2H5 is nitrosated to give nitro‐PhIP, wh...

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Bibliographic Details
Published in:Journal of labelled compounds & radiopharmaceuticals 2001-05, Vol.44 (6), p.405-411
Main Authors: Tanga, Mary J., Bupp, James E., Bradford, Wallace W.
Format: Article
Language:English
Subjects:
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine
boron trifluoride phosphoric-2H3 acid complex
Chemistry
deuterium
Exact sciences and technology
food mutagens
heterocyclic amines
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
N-hydroxy-PhIP
nitro-PhIP
Organic chemistry
PhIP
Preparations and properties
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Summary: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–2H5 is nitrosated to give nitro‐PhIP, which is then reduced to N‐hydroxy–PhIP–2H5. Copyright © 2001 John Wiley & Sons, Ltd.
ISSN:0362-4803
1099-1344
DOI:10.1002/jlcr.468