Synthesis of (2S,3S)-2-amino-3-methylpent-4-ynoic acid, a precursor amino acid for the preparation of tritium- or deuterium-labelled peptide in the isoleucine residue
Synthesis of (2S,3S)-2-amino-3-methylpent-4-ynoic acid, a precursor amino acid for the preparation of tritium- or deuterium-labelled peptide in the isoleucine residue
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(2S,3S)-2-氨基-3-甲基戊-4-炔酸的合成，这是一种用于制备异亮氨酸残基中氚或氘标记肽的前体氨基酸
DOI：
10.1039/p19930000489
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发表时间：
1993
期刊：
影响因子：
--
通讯作者：
S. Baba
中科院分区：
文献类型：
--
作者：
H. Hasegawa;S. Arai;Y. Shinohara;S. Baba
报道了 (2S,3S)-2-氨基-3-甲基戊-4-炔酸 (Amp)1 的合成、将其掺入肽链以及异亮氨酸残基中氘标记肽的制备。氨基酸1由3-氯丁-1-炔分三步合成。采用手性固定相柱进行HPLC测定，氨基酸1的光学纯度大于99%(ee)。基于Fmoc策略，通过固相合成法合成了Tyr-Amp-Leu。三肽经催化氘化产生 Tyr-[2H]lle-Leu。通过快原子轰击质谱（FAB-MS）和 13C NMR 光谱研究了氘的分布，证实氘完全位于异亮氨酸残基上。
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 99%(ee). Tyr-Amp-Leu was synthesized by solid-phase synthesis based on Fmoc strategy. The tripeptide was deuteriated catalytically to yield Tyr-[2H]lle-Leu. The distribution of deuterium was investigated by fast-atom-bombardment mass spectrometry (FAB-MS) and 13C NMR spectroscopy, which confirmed that the deuterium was located entirely at the isoleucine residue.