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

Tanga Mary J. | Zendy; Bupp James E. | Zendy; Bradford Wallace W. | Zendy

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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.

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