Synthesis of (2S,3S)-2-Amino-3-methylpent-4-ynoic Acid, a Precursor Amino Acid for the Preparation of Tritium- or Deuterium-Labeled 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-Labeled Peptide in the Isoleucine Residue.
复制标题
(2S,3S)-2-氨基-3-甲基戊-4-炔酸的合成，这是一种用于在异亮氨酸残基中制备氚或氘标记肽的前体氨基酸。
DOI：
10.1002/chin.199323261
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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
本文报道了（2S，3S）-2-氨基-3-甲基异炔诺酮-4-炔酸的合成，并将其掺入到肽链中，以及在异亮氨酸残基上制备氘标记肽。以3-氯丁-1-炔为起始原料，经三步反应合成了氨基酸1。氨基酸1的光学纯度用HPLC手性固定相柱测定，并发现大于99%（ee）。采用Fmoc固相合成法合成了Tyr-B-Leu。三肽经催化氘化得到Tyr-[2 H] Ile-Leu。通过快原子轰击质谱（FAB-MS）和13 C 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.