期刊
JOURNAL OF MASS SPECTROMETRY
卷 36, 期 9, 页码 998-1012出版社
JOHN WILEY & SONS LTD
DOI: 10.1002/jms.203
关键词
anabolic steroids; gas chromatography; mass spectrometry; structure confirmation; mass spectra interpretation; Koenigs-Knorr reaction; selective conjugation
The steroid glucuronide conjugates of 16,16,17-d(3)-testosterone, epitestosterone, nandrolone (19-nortestosterone),16,16,17-d(3)-nortestosterone methyltestosterone,metenolone,mesterolone,5 alpha -androstane-3 alpha, 17 beta -diol, 2,2,3,4,4-d(5)-5 alpha -androstane-3 alpha ,17 beta -diol, 19-nor-5 alpha -androstane-3 alpha ,17 beta -diol, 2,2,4,4-d(4)-19-nor-5 alpha -androstane-3 alpha ,17 beta -diol and 1 alpha -methyl-5 alpha -androstane-3 alpha/beta, 17 beta -diol were synthesized by means of the Koenigs-Knorr reaction. Selective 3- or 17-O-conjugation of bis-hydroxylated steroids was performed either by glucuronidation of the corresponding steroid ketole and subsequent reduction of the keto group or via a four-step synthesis starting from a mono-hydroxylated steroid including (a) protection of the hydroxy group, (b) reduction of the keto group, (c) conjugation reaction and (d) removal of protecting groups. The mass spectra and fragmentation patterns of all glucuronide conjugates were compared with those of the commercially available testosterone glucuronide and their characterization was performed by gas chromatography/mass spectrometry and nuclear magnetic resonance spectroscopy. For mass spectrometry the substances were derivatized. to methyl esters followed by trimethylsilylation of hydroxy groups and to pertrimethylsilylated products using labelled and unlabelled trimethylsilylating agents. The resulting electron ionization mass spectra obtained by GC/MS quadrupole and ion trap instruments, full scan and selected reaction monitoring experiments are discussed, common and individual fragment ions are described and their origins are proposed. Copyright (C) 2001 John Wiley & Sons, Ltd.
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