Mass spectrometry of cytokinin metabolites. Per(trimethylsilyl) and permethyl derivatives of glucosides of zeatin and 6-benzylaminopurine

John K. MacLeod*, Roger E. Summons, David S. Letham

*Corresponding author for this work

    Research output: Contribution to journalArticle

    44 Citations (Scopus)

    Abstract

    The mass spectra of the Me 3Si and permethylated derivatives of a comprehensive series of synthetic isomeric glucosides of the cytokinins zeatin and 6-benzylaminopurine (6-BAP) have been recorded by combined gas chromatography-mass spectrometry. Comparison of these spectra with those obtained for a number of glucosyl metabolites of zeatin and 6-BAP allows unambiguous structural assignments to be made. Detailed analysis of the mass spectral fragmentation patterns indicate that, a priori, it should be possible to assign the sugar ring size (furanose vs. pyranose) in such compounds on the basis of characteristic fragment ion intensities. Mass spectra of the Me 3Si derivatives show more significant isomer differences than the corresponding permethylated compounds and their method of preparation appears less prone to multiple product formation. A thermal 1,3 migration of the sugar moiety from N 3 to N 9 was observed in the GC-MS of the derivatives of the 3-β-D-glucopyranoside of 6-BAP.

    Original languageEnglish
    Pages (from-to)3959-3967
    Number of pages9
    JournalJournal of Organic Chemistry
    Volume41
    Issue number25
    Publication statusPublished - 1976

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