Product Ion Studies of Diastereomeric Benzo[ghi]fluoranthene Tetraols by Matrix-assisted Laser Desorption/ionization Time-of-flight Mass Spectrometry and Post-source Decay

Overview

Journal J Am Soc Mass Spectrom

Specialty Chemistry

Date 2001 Apr 27

PMID 11322184

Authors

D M Huffer

H F Chang

B P Cho

L K Zhang

M P Chiarelli

Affiliations

Soon will be listed here.

Abstract

The product ion formation characteristics of the four diastereomeric tetrahydroxy benzo[ghi]fluoranthene compounds formed by hydrolysis of the syn and anti diastereomers of trans-3,4-dihydroxy-5,5a-epoxy-3,4,5,5a-tetrahydrobenzo[ghi]fluoranthene are studied using matrix-assisted laser desorption/ionization and post-source decay (PSD) to determine a correlation between the fragmentation characteristics of these tetraols and the structures of the diol-epoxide diastereomers from which they are hydrolyzed. The tetraols formed by the trans ring opening of the diol epoxides during hydrolysis yield product ion spectra specific for the syn and anti configurations of their precursor diol epoxides. All four diastereomeric tetraols form product ions by the losses of one and/or two water molecules in varying proportions when lithium-cationized molecule ions (m/z 301) are selected for PSD product ion analysis. The differences in the PSD spectra of these four Li+-cationized molecules are rationalized in terms of a water loss mechanism that involves the 1,2 elimination of a hydrogen atom and hydroxyl group that are cis with respect to each other on adjacent carbons.

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