Evidence for an NIH shift as the origin of the apparently anomalous distribution of deuterium in estragole from Artemisia dracunculus.
Feeding experiments of [2-(2)H]- and [4'-(2)H]phenylalanine in Artemisia dracunculus validate the hypothesis that the marked difference in deuterium content at the natural abundance level between the aromatic carbons of estragole (1) is due to an NIH shift during the hydroxylation of the benzene ring.
Manitto
P
P
Dipartimento di Chimica Organica e Industriale, Università di Milano and Centro di Studio sulle Sostanze Organiche Naturali, CNR, Via Venezian 21, 20133 Milano, Italy. paolo.manitto@unimi.it
Monti
D
D
Speranza
G
G
D000081248:Allylbenzene Derivatives; D000840:Anisoles / Q000737:chemistry* / Q000378:metabolism; D019306:Artemisia / Q000737:chemistry* / Q000378:metabolism; D003903:Deuterium; D007553:Isotope Labeling; D009682:Magnetic Resonance Spectroscopy; D009822:Oils, Volatile / Q000737:chemistry* / Q000378:metabolism; D010649:Phenylalanine / Q000378:metabolism; D010946:Plants, Medicinal
D000081248:Allylbenzene Derivatives; D000840:Anisoles; D009822:Oils, Volatile; D010649:Phenylalanine; C007633:estragole; D003903:Deuterium