The synthesis and chromatography of peptine nitriles

Di- and tripeptide nitriles, glycylaminoacetonitrile (Gly-AAN), diglycylaminoacetonitrile (Gly-Gly-AAN), alany-alpha-aminopropionitrile (Ala-APN), and dialanyl-alpha-aminopropionitrile (Ala-Ala-APN) were synthesized first. These peptide nitriles and related peptides and peptide amides were analyzed by means of ion-exchange chromatography. The every two diastereomers of dialanine, dialanine amide, and Ala-APN were separated into two peaks by using a pH 3.25 buffer as an eluent. The four isomers of trialanine, trialanine amide, and Ala--Ala APN gave four, two, and one peak, respectively under the same conditions. The trimethylsilyl derivatives of alanyl peptides and related compounds were analyzed by means of gas chromatogrpahy combined with mass-spectrometry. The parent (M+ and/or M+-15) and other mass numbers observed in their mass-spectra supported the introduction of various numbers of trimethylsilyl groups.