The mass spectrometry of 2-methylthio (glyco) oxazoline derivatives of pentoses and hexoses

The fragmentation of 2-methylthio(glyco)oxazolines under electron impact has been investigated by low- and high-resolution mass spectrometry. Field desorption was used in those cases where the molecular ion was weak or missing. Fragmentation pathways were determined by monitoring metastable transitions and through the use of labeled compounds. The results support the anticipated structure for these compounds and show the sensitivity of the mass spectra toward ring size.

[1]  B. Coxon,et al.  Synthesis of nitrogen-15-labeled 2-amino(glycofurano)oxazolines via glycosylamine intermediates☆ , 1983 .

[2]  N. Oppenheimer,et al.  A new, facile synthesis of 2-amino-(pento- and hexo-furano)oxazoline derivatives , 1983 .

[3]  P. Traldi,et al.  The fragmentation of 2-aminooxazoles under electron impact† , 1979 .

[4]  W. Wierenga,et al.  Introduction of a new 1,3-electrophilic carbon-nitrogen-carbon annulation reagent in the synthesis of 2,2'-anhydrodihydro-5-azathymidine , 1978 .

[5]  E. Hessler.  An efficient synthesis of 1-beta-D-arabinofuranosylcytosine. , 1976, The Journal of organic chemistry.

[6]  R. Sanchez,et al.  2,2-Anhydropyrimidine nucleosides. Novel syntheses and reactions. , 1973, The Journal of organic chemistry.

[7]  A. Holý.  Nucleic acid components and their analogues. CLVI. Preparation of enantiometric 1-(α-xylofuranosyl), 1-(α-lyxofuranosyl), and 1-(2-deoxy-α-lyxofuranosyl) derivatives of uracil and cytosine , 1973 .

[8]  J. McCloskey,et al.  Mass spectrometry of cyclonucleosides. , 1972, The Journal of organic chemistry.

[9]  A. Holý.  Nucleic acid components and their analogues. CLIII. Preparation of 2'-deoxy-L-ribonucleosides of the pyrimidine series , 1972 .

[10]  D. Gish,et al.  Nucleic acids. 12. Synthesis of the L enantiomer of 1- -arabinofuranosylcytosine and of O 2 ,O 2' -anhydro-1- -D-arabinofuranosylcytosine. , 1971, Journal of medicinal chemistry.

[11]  L. Orgel,et al.  Studies in prebiotic synthesis. V. Synthesis and photoanomerization of pyrimidine nucleosides. , 1970, Journal of molecular biology.

[12]  K. Biemann,et al.  Application of Mass Spectrometry to Structure Problems. XIII.1 Acetates of Pentoses and Hexoses2 , 1963 .