Gas chromatographic and mass spectrometric behaviour of O-alkylserines as their N-trifluoroacetyl butyl esters

✍ Scribed by Munenori Sakamoto; Makoto Nishimoto; Natsuko Kohara; Fumi Masuko

• Publisher: Elsevier Science
• Year: 1987
• Tongue: English
• Weight: 992 KB
• Volume: 411
• Category: Article
• ISSN: 1873-3778
• DOI: 10.1016/s0021-9673(00)93977-3

✦ Synopsis

Four 0-alkylserines were prepared from the corresponding alkyl O-alkyl-adehydroserinates by hydrogenation, followed by hydrolysis. The gas chromatographic behaviour of N-trifluoroacetyl butyl ester (BTFA) and N-trifluoroacetyl alkyl ester (RTFA) derivatives of the alkylserines and RTFA derivatives of the alkyldehydroserines was studied on columns of OV-17 and Dexsil 300 GC in relation to the chemical structures of the amino acids. Alkyldehydroserine derivatives were more polar and eluted more slowly than alkylserine derivatives, which eluted as fast as alkylglycine derivatives of the same molecuiar weight. The stability of 0-propylserine under the conditions for acid hydrolysis of proteins was compared with that of Opropyltyrosine and S-propylcysteine: the stability increased in the order O-propyltyrosine < 0-propylserine < S-propylcysteine. Mass spectrometric fragmentation patterns (electron and chemical ionization modes) of BTFA and/or RTFA derivatives of 0-alkylserines and 0-alkyldehydroserines are given with those of BTFA derivatives of S-alkylcysteines.