Mass spectra of nucleoside derivatives

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Abstract
The mass spectra of derivatives of uridine, adenosine, cytidine and guanosine are recorded. Derivatization techniques include permethylation, acetylation, trifluoroacetylation, trimethylsilylation and the synthesis of 2′,3′‐O‐isopropylidenes and 2′,3′‐O‐phenylboronic esters. Sequential derivatization by a selective combination of some of these procedures results in nucleosides which are blocked with a characteristic group at the cis 1,2 diol position, and, which contain other substituent groups that enhance the volatility of the compound. The specific substitution at the cis‐glycol region has been shown to be particularly useful in asymmetrically derivatizing dinucleoside phosphates since certain fragment ions from their mass spectra indicate the sequence of the two nucleoside components. Sequence isomers such as adenylyl‐(3′‐5′)‐uridine and uridylyl‐(3′‐5′)‐adenosine can be unambiguously distinguished.