Electrospray tandem mass-spectrometric analysis of diastereo- and stereoisomeric pyrimidine nucleoside analogues based on the 1,3-dihydrobenzo[c]furan core

Recent Developments in Mass Spectrometry for the Characterization of Nucleosides, Nucleotides, Oligonucleotides, and Nucleic Acids

“…Low-energy collision tandem mass spectrometric analysis of the various protonated molecules [M + H] + and cluster ions such as [M + Na] + , [2M + H] + , and [2M + Na] + confirmed the characteristic fingerprint pattern obtained in the conventional electrospray spectra . In the tandem mass spectra obtained for the precursor ion [M + H] + at m / z 365 isolated from nucleosides 28 and 29 the differences between the product-ion intensities within each enantiomeric pair were, as expected, not significant.…”

Synthesis of C-Arylnucleoside Analogues

“…From 1996 to 2006 Len and co-workers described the synthesis of d4T analogues having a benzo[ c ]furan core. Various strategies including racemic synthesis and asymmetric synthesis have been reported by his group, all of them starting from phthalaldehyde [46,47,48,49,50,51,52,53,54,55]. In parallel to this work, the Liu group reported the racemic synthesis of benzo[ c ]furan nucleoside analogues [56].…”

“…The related enantiomers analogous to L-nucleosides were synthesized using the same strategy but employing AD-mix β. Using the same strategy, Len and co-workers [46,47,48,49,50,51,52,53,54,55] reported the synthesis of d4T analogues 216 – 220 (Figure 12).…”

Gas‐phase fragmentation reactions of protonated benzofuran‐ and dihydrobenzofuran‐type neolignans investigated by accurate‐mass electrospray ionization tandem mass spectrometry

“…Despite the broad scope of DBN and BN biological activities, studies dedicated to the fragmentation of these compounds by ESI‐MS/MS are still scarce in the literature. Len and co‐workers employed ESI‐MS/MS to identify diasteroisomeric dihydrobenzofuran‐1‐yl thyamines and a novel 1,3‐dihydrobenzofuran nucleoside on the basis of product ion spectra of singly protonated and sodium complex of selected precursor ions by low‐energy collision‐induced dissociation (CID) . Yang and co‐workers studied fragmentation of coumestans, pterocarpenes, benzofurans, and isoflavones present in Hedysarum multijugum and identified 29 compounds in the corresponding methanol extract, including five benzofurans, which exhibited characteristic losses, like CO and H 2 O .…”

“…Len and co-workers employed ESI-MS/MS to identify diasteroisomeric dihydrobenzofuran-1-yl thyamines and a novel 1,3-dihydrobenzofuran nucleoside on the basis of product ion spectra of singly protonated and sodium complex of selected precursor ions by low-energy collision-induced dissociation (CID). 14 Yang and co-workers studied fragmentation of coumestans, pterocarpenes, benzofurans, and isoflavones present in Hedysarum multijugum and identified 29 compounds in the corresponding methanol extract, including five benzofurans, which exhibited characteristic losses, like CO and H 2 O. 15 Kang and co-workers described that H 2 O loss from protonated benzofuran glycosides present in Saposhnikovia divaricata root extracts involves dihydrofuran ring cleavage.…”