Fast-atom bombardment mass spectrometry study of N-benzoyl-tauryl amino acids

✍ Scribed by Yali Kong; Meiyu He; Sheng Jin; Xiaoran He

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 133 KB
• Volume: 11
• Category: Article
• ISSN: 0951-4198
• DOI: 10.1002/(sici)1097-0231(19971015)11:15<1731::aid-rcm933>3.0.co;2-g

✦ Synopsis

Seven new compounds, that are isosteric with phosphonate compounds on the basis of structure and charge distribution, have been synthesized. These compounds could be important in the design and synthesis of hapten molecules for catalytic antibodies. Mass spectrometric data for these compounds were obtained by fast-atom bombardment and fragmentation mechanisms were analysed using mass-analysed ion kinetic energy spectrometry. The elemental compositions and structures of some important fragment ions were verified with high-resolution data and also confirmed by deuteration. We discovered that all the compounds show [2M + H] + peaks and that the cleavage of the terminal amino acid is caused by rearrangement of H on the -NH-of the benzamido group via a protonated six-ring transition state. Also of importance is the fact that one hydrogen of the neutral molecule HCOOH, which is lost on fragmentation, is derived from the active hydrogen of the terminal amino acid, as was demonstrated by deuteration.