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Synthesis and Mass Spectrometry Analysis of Mimosine-Containing Peptides
International Journal of Peptide Research and Therapeutics ( IF 2.5 ) Pub Date : 2020-06-29 , DOI: 10.1007/s10989-020-10092-w
Remigiusz Bąchor , Enrico Randaccio , Joanna I. Lachowicz , Piotr Stefanowicz , Valeria M. Nurchi , Zbigniew Szewczuk

Non-proteinogenic amino acids are widely explored group of compounds due to their chemical properties and great potential of application in the combinatorial chemistry, medicinal investigation etc. Therefore the synthetic methods of their incorporation to the peptide chain are required. l-Mimosine, (S)-α-amino-β-(3-hydoxy-4-oxo-1,4-dihydropyridin-1-yl)-propanoic acid), is a plant amino acid, known to induce apoptosis in human pancreatic cancer xenografts. Here we present our investigations on the synthesis of mimosine-containing peptide and their ESI-MS/MS analysis. We successfully applied Fmoc-protected mimosine a with a free hydroxy ketone group for efficient peptide synthesis in the presence of HATU as a coupling reagent without the formation of side products. Additionally the tandem mass spectrometry analysis revealed the characteristic loss of the heterocyclic ring from mimosine residue side chain. The described method allows insertion of mimosine residue at any endo-position within a peptide sequence. The obtained results may be useful in the synthesis and mass spectrometry analysis of various mimosine-containing peptides.



中文翻译:

含亚氨酸肽的合成及质谱分析

非蛋白质氨基酸由于其化学性质以及在组合化学,医学研究等方面的巨大应用潜力而被广泛研究,因此,需要将其掺入肽链的合成方法。-Mimosine,(小号)-α-氨基-β-(3-羟基4-氧代-1,4-二氢吡啶-1-基)-丙酸)是一种植物氨基酸,已知可诱导人胰腺癌异种移植物中的细胞凋亡。在这里,我们介绍了我们的研究,含亚氨酸肽的合成及其ESI-MS / MS分析。在HATU作为偶联剂存在下,我们成功地将带有游离羟基酮基的Fmoc保护的含羞草碱a用于有效的肽合成,而不会形成副产物。另外,串联质谱分析揭示了含羞草残基侧链上杂环的特征性损失。所描述的方法允许在肽序列内的任何内位插入亚氨酸残基。所获得的结果可用于各种含含亚氨酸肽的合成和质谱分析。

更新日期:2020-06-29
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