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Mass spectrometric investigation of some α‐trifluoromethyl‐α‐amino acids
Author(s) -
Rimlinger Joseph,
Zanda Matteo,
Bravo Pierfrancesco,
Favretto Donata,
Traldi Pietro
Publication year - 1997
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/(sici)1096-9888(199709)32:9<1002::aid-jms572>3.0.co;2-c
Subject(s) - chemistry , protonation , trifluoromethyl , oxygen atom , proton affinity , metastability , ion , oxygen , fluorine , proton , amino acid , medicinal chemistry , mass spectrometry , computational chemistry , organic chemistry , stereochemistry , molecule , chromatography , biochemistry , alkyl , physics , quantum mechanics
The fast atom bombardment‐induced mass spectrometric behaviour of four fluorinated α‐amino acids was studied in detail with the aid of metastable ion studies and accurate mass measurements. Comparison with the behaviour of unfluorinated analogues suggests that the presence of fluorine makes the carbonylic oxygen the most prone to protonation. This hypothesis was confirmed by AM1 semiempirical calculations which indicate that the carbonylic oxygen of the carboxyl group exhibits, in the case of fluorinated compounds only, the highest proton affinity. © 1997 John Wiley & Sons, Ltd.