Amino acid functionalisation using the 2-phosphaethynolate anion. A facile route to (phosphanyl)carbonyl-amino acids.
Amino acid functionalisation using the 2-phosphaethynolate anion. A facile route to (phosphanyl)carbonyl-amino acids.
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DOI：
10.1039/c7cc01285c
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发表时间：
2017-06
影响因子：
4.9
通讯作者：
Érica N. Faria;A. Jupp;J. Goicoechea
中科院分区：
文献类型：
--
作者：
Érica N. Faria;A. Jupp;J. Goicoechea
我们描述了 2-磷酸乙炔酸阴离子 (PCO-) 与对映体纯 α-氨基酸 (AA) 的反应性，导致形成带有手性官能团的新型膦甲酰胺盐。除了一种氨基酸外，所有试验的氨基酸都定量地发生这些转化（发现碱性氨基酸精氨酸不具有反应性）。所得离子物质可以容易地质子化以提供N-(膦酰基)羰基-氨基酸，这是一组带有伯膦官能团的新型氨基酸。
We describe the reactivity of the 2-phosphaethynolate anion (PCO-) towards enantiomerically pure α-amino acids (AAs) resulting in the formation of novel salts of phosphinecarboxamides bearing chiral functionalities. These transformations occurred quantitatively with all but one of the amino acids trialled (the basic amino acid arginine was found to be unreactive). The resulting ionic species can be readily protonated to afford N-(phosphanyl)carbonyl-amino acids, a novel group of amino acids bearing primary phosphine functionalities.