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Mass spectrometry and chromatography of t-butyldimethylsilyl derivatives of cytokinin bases

Authors
  • Hocart, Charles H.
  • Wong, O.Choon
  • Letham, David S.
  • Tay, Stephen A.B.
  • MacLeod, John K.
Type
Published Article
Journal
Analytical Biochemistry
Publisher
Elsevier BV
Publication Date
Jan 01, 1986
Volume
153
Issue
1
Pages
85–96
Identifiers
DOI: 10.1016/0003-2697(86)90065-5
Source
Elsevier
Keywords
License
Unknown

Abstract

Di-(t-butyldimethylsilyl) derivatives of the cytokinin bases zeatin, cis-zeatin, and dihydrozeatin may be prepared quantitatively in the presence of dimethylaminopyridine. These derivatives have good gas chromatographic properties and are very suitable for gas chromatography-mass spectrometry analysis of cytokinin bases. The t-butyldimethylsilyl (tBuDMS) group at N-9 may be selectively hydrolyzed and the resulting mono- O-silyl derivatives are sufficiently stable to be subjected to thin-layer chromatography and high-performance liquid chromatography. The mass spectral fragmentation of the mono- and di-tBuDMS derivatives of adenine, zeatin, cis-zeatin, and dihydrozeatin and also of the mono-tBuDMS derivatives of N 6-isopentenyladenine and 6-benzylaminopurine have been rationalized. The 9-tBuDMS moiety was characterized by an elimination of isobutene (M-56) and of isobutene plus a methyl radical (M-56-15).

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