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Formation of β‐carbolines from 1‐[(1′ ‐carboxy‐2′‐indol‐3′‐yl‐ethyl)amino]‐1‐deoxy‐ D ‐fructose under electron impact conditions
Author(s) -
Yaylayan Varoujan,
Paré J. R. Jocelyn,
Laing Richard,
Sporns Peter
Publication year - 1990
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210250304
Subject(s) - amadori rearrangement , tryptophan , chemistry , intramolecular force , fructose , maillard reaction , nucleophile , stereochemistry , medicinal chemistry , amino acid , biochemistry , glycation , receptor , catalysis
Interest in β‐carbolines has recently increased owing to their detection in human tissue and in some food products; one of the possible sources of their formation in food is the Amadori rearrangement product (ARP) of tryptophan with glucose, l‐[(1′‐carboxy‐2′‐indol‐3′‐ylethyl)amino] ‐1‐deoxy‐ D ‐fructose. Based on the intermediates identified in the high‐resolution electron impact spectrum of the tryptophan Amadori product and by B/E and B 2 /E linked‐scan experiments, a mechanism is proposed for their formation under electron impact conditions. The proposed mechanism is an intramolecular nucleophilic substitution reaction of the dehydrated tryptophan ARP, leading to the formation of 3‐substituted β‐carbolines; this mechanism might shed some light on the origin of their abundant formation in food.