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Structure elucidation of annoheptocins, two new heptahydroxylated C37 acetogenins by high-energy collision-induced dissociation tandem mass spectrometry

✍ Scribed by Edna L. Meneses da Silva; François Roblot; Reynald Hocquemiller; Laurent Serani; Olivier Laprévote

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 136 KB
Volume: 12
Category: Article
ISSN: 0951-4198
DOI: 10.1002/(sici)1097-0231(19981215)12:23<1936::aid-rcm412>3.0.co;2-8

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✦ Synopsis

Collision-induced dissociation (CID) of lithiated molecules generated by liquid SIMS (LSIMS) from two new natural compounds, annoheptocin A and B, led to their structural elucidation. Mass spectrometry (MS) and tandem mass spectrometry (MS/MS) investigations of their acetonide derivatives displayed obvious differences of reactivity of the lithiated dioxane and dioxolane rings towards CID. The 1,3-dioxane (sixmembered) ring could be the target of hydrogen rearrangement processes, leading to the formation of a tetrahydrofuran ring through the loss of a molecule of acetone.

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