Journal of the Chemical Society. Perkin transactions I p. 489 - 494 (1993)
Update date:2022-08-06
Topics:
Hasegawa, Hiroshi
Arai, Shinichi
Shinohara, Yoshihiko
Baba, Shigeo
The synthesis of (2S,3S)-2-amino-3-methylpent-4-ynoic acid (Amp) 1, its incorporation into a peptide chain, and the preparation of a deuterium-labelled peptide in the isoleucine residue are reported.Amino acid 1 was synthesized in three steps from 3-chlorobut-1-yne.The optical purity of amino acid 1 was determined by HPLC with a chiral stationary-phase column and was found to be more than 99percent (ee).Tyr-Amp-Leu was synthesized by solid-phase synthesis based on Fmoc strategy.The tripeptide was deuteriated catalytically to yield Tyr-<(2)H>Ile-Leu.The distribution of deuterium was investigated by fast-atom-bombardment mass spectrometry (FAB-MS) and (13)C NMR spectroscopy, which confirmed that the deuterium was located entirely at the isoleucine residue.
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