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Determining double‐bond positions in monoenoic 2‐hydroxy fatty acids of glucosylceramides by gas chromatography‐mass spectrometry
Author(s) -
Imai Hiroyuki,
Yamamoto Kohei,
Shibahara Akira,
Miyatani Shuichi,
Nakayama Takao
Publication year - 2000
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02664774
Subject(s) - chemistry , double bond , mass spectrometry , dimethyl disulfide , adduct , chromatography , gas chromatography , gas chromatography–mass spectrometry , mass spectrum , hydrolysate , time of flight mass spectrometry , organic chemistry , ion , hydrolysis , ionization , sulfur
We applied a gas chromatography‐mass spectrometry (GC‐MS) method using dimethyl disulfide (DMDS) adducts and were able to determine the double‐bond positions in monounsaturated 2‐hydroxy fatty acids (2‐HFA). 2‐HFA methyl esters, prepared from the hydrolysate of Arabidopsis thaliana leaf glucosylceramides, were acetylated and methylthiolated. GC‐MS analysis of the resulting DMDS adducts showed simple mass spectra with recognizable molecular ions and a series of key fragment ions indicating the original double‐bond positions in the aliphatic chain. Based on this GC‐MS elucidation, we confirmed that Arabidopsis leaf glucosylceramides have C 22 , C 23 , C 24 , C 25 , and C 26 chain length 2‐HFA with monounsaturation, and all their double bonds are placed at the n−9 position. This procedure is simple, time efficient, and highly sensitive.