Mass spectrometric evidence for the anomalous chemical behavior of 11-dehydrothromboxane B2.

Abstract:

:When we subjected 11-dehydrothromboxane B2 (11-DTXB2), a metabolite of arachidonic acid, to standard chemical derivatization procedures we obtained a mixture of several products. Separation of the components was carried out by gas chromatography and their identification was accomplished through the study of their mass spectra, which are presented here. Anomalous behaviors include methylation of allylic and alcoholic hydroxyl groups by diazomethane, unusually slow derivatization of one of the hydroxyl groups with N,O-bis(trimethylsilyl)-trifluoroacetamide (BSTFA) and etherification of another with ethanol. The underlying causes of these abnormal behaviors are not obvious, but appear to be related, at least in part, to the opening/closure of a lactone ring in the molecule. These observations have some bearing on the development of valid procedures for GC-MS quantification of this important marker of thromboxane A2 synthesis in vivo, and of similar compounds.

journal_name

Chem Phys Lipids

authors

Ferretti A,Flanagan VP

doi

10.1016/0009-3084(95)02452-o

subject

Has Abstract

pub_date

1995-08-01 00:00:00

pages

33-40

issue

1

eissn

0009-3084

issn

1873-2941

pii

000930849502452O

journal_volume

77

pub_type

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