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Identification of glucopyranosyl‐β‐1,4‐glucopyranosyl‐β‐1‐ N ‐oxindole‐3‐acetyl‐ N ‐aspartic acid, a new IAA catabolite, by liquid chromatography/tandem mass spectrometry
Author(s) -
Östin Anders,
Catalá Carmen,
Chamarro Jesus,
Sandberg Göran
Publication year - 1995
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.1190300710
Subject(s) - chemistry , chromatography , fast atom bombardment , oxindole , mass spectrometry , tandem mass spectrometry , aspartic acid , diastereomer , hydrolysis , acid hydrolysis , liquid chromatography–mass spectrometry , indole 3 acetic acid , indole test , amide , organic chemistry , amino acid , biochemistry , auxin , gene , catalysis
Abstract [5‐ 3 H, 13 C 6 ] Indole‐3‐acetic acid was fed to immature pericarp segments from fruits of tomato ( Lycopersicon esculentum Mill., cv. Moneymaker), resulting, after 24 h of incubation, in five radiolabelled peaks when analysed by reversed‐phase high‐performance liquid chromatography with radiocounting. The fractions were numbered in order of decreasing polarity. Fractions 4 and 5 had earlier been shown to contain indole‐3‐acetyl‐ N ‐aspartic acid and indole‐3‐acetyl‐ O ‐glucose. Based on results from strong alkaline hydrolysis, it had been concluded that fractions 1 and 3 contain an amide conjugate with a modified indole ring. This paper presents data supporting the structure of the labelled compounds in fractions 1 and 3 to be diastereomers of glucopyranosyl‐β‐1,4‐glucopyranosyl‐β‐1‐ N ‐oxindole‐3‐acetyl‐ N ‐aspartic acid. The identification of glucopyranosyl‐β‐1‐ N ‐oxindole‐3‐acetyl‐ N ‐aspartic acid in fraction 2 is also reported. These structures were elucidated by liquid chromatography/frit fast atom bombardment tandem mass spectrometry.