Formaldehyde adducts of glutathione. Structure elucidation by two-dimensional n.m.r. spectroscopy and fast-atom-bombardment tandem mass spectrometry
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Aqueous mixtures of formaldehyde and glutathione react to form a variety of cyclized adducts in addition to S-hydroxymethylglutathione. The adducts are in labile equilibrium with each other and are not readily separated. The structures of two of the other major adducts were determined by concerted application of 13C-1H two-dimensional chemical-shift correlation, fast-atom-bombardment mass spectrometry and tandem mass spectrometry to the adduct mixtures in aqueous solution.Keywords:
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Steroidal allylic alcohols formed Na+ adduct ion peaks [M+Na]+ by the addition of NaCl in FAB mass spectrometry. A comparison of the intensities of the adduct ion peaks of allylic alcohols with those of the corresponding saturated alcohols and olefin suggested that the olefinic double bond and the proximal hydroxyl group had coordinated to Na+. The adduct ion was stable and did not undergo dehydroxylation. We suggest that the Na+ adduction will be useful for the molecular weight determination of allylic alcohols which are susceptible to dehydroxylation under FAB mass spectrometric conditions. Na+ adduct ions of alpha,beta-unsaturated carbonyl compounds were also investigated.
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Aqueous mixtures of formaldehyde and glutathione react to form a variety of cyclized adducts in addition to S-hydroxymethylglutathione. The adducts are in labile equilibrium with each other and are not readily separated. The structures of two of the other major adducts were determined by concerted application of 13C-1H two-dimensional chemical-shift correlation, fast-atom-bombardment mass spectrometry and tandem mass spectrometry to the adduct mixtures in aqueous solution.
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Analysis of cyclodextrins using fast atom bombardment/mass spectrometry and tandem mass spectrometry
The combination of fast atom bombardment/mass spectrometry (FAB/MS) and FAB with tandem mass spectrometry (FAB/MS/MS) was used for the characterization of nearly 30 chemically modified cyclodextrins. Optimum FAB/MS analysis conditions as well as both positive and negative ion FAB data are presented. In addition, FAB/MS and FAB/MS/MS were used to characterize the in vitro reaction products of β-cyclodextrin (βCD) with soman, an organophosphorous nerve agent. The main product identified from the reaction was a covalently bound soman–βCD conjugate.
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Abstract We have examined the applicability of tandem mass spectrometry to the structural elucidation of polyether compounds. The polyether toxin named yessotoxin was isolated from scallops which were implicated in food poisoning. The toxin consists of fused polycyclic ethers as does ciguatoxin, and bears two sulfate esters in the molecule. The negative‐ion fast‐atom bombardment tandem mass spectrum of the toxin showed a series of ions due to fragmentation at positions characteristic of cyclic ethers. With the mass spectrometric data alone, we succeeded in assigning the number and location of eleven ether rings in yessotoxin, which agreed with those previously deduced by nuclear magnetic resonance studies.
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Positive fast atom bombardment tandem mass spectrometry is demonstrated to be an effective technique for determination of crude aflatoxins and sterigmatocystin-related compounds. The molecular ion was selected by the first system and bombarded to produce characteristic daughter ions that could be used to identify mycotoxins in mixtures and with the same molecular weight.
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Positive-ion fast atom bombardment tandem mass spectrometry has been used in the characterization of non-, mono-, di- and trisulfated disaccharides from heparin and heparan sulfate. The positional isomers of sulfate groups of monosulfated disaccharides have been distinguished from each other by positive-ion fast atom bombardment tandem mass spectra, which provide an easy way of identifying the positional isomers. The fast atom bombardment collision-induced dissociation mass spectrometry/mass spectrometry technique was also applied successfully to the characterization of di- and trisulfated disaccharides.
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Mass spectrometry is a very powerful technique in the rapid determination of the structure of peptides. Synthetic peptides may be analyzed fully protected and partially or completely deprotected. Often, the molecular weight alone, readily obtained by fast atom bombardment mass spectrometry, is sufficient to establish the nature of the product and whether it is the expected one. Tandem mass spectrometry can be used to identify unexpected reaction products which sometimes form during removal of protecting groups, the incomplete removal of such groups, as well as to distinguish between structural isomers.
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Glycerophospholipids
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