N-磷酰化肽酯及小肽与氨基酸相互作用的ESI-MS研究

Study on Interaction Between N-phosphoryl Dipeptides (or Methyl Esters) and Amino Acids by ESI-MS

采用ESI-MS研究了一系列结构具有可比性的N-二异丙氧基磷酰化肽酯及小肽同20种蛋白氨基酸及3种D型氨基酸(D-Ala、D-Ser、D-Phe)的非共价相互作用。结果表明,可形成π-π共轭体系的芳香环,可显著增强磷酰化肽酯及小肽与氨基酸的相互作用力,π-π堆积力是首要的非共价相互作用力;可形成氢键的极性基团有利于形成复合物,但能否形成氢键还要受到分子柔顺性的影响;另外,分子大小、空间位阻对复合物的形成也有影响;而氨基酸的手性对它们的相互作用在质谱条件下没有表现出影响。

Non-covalent interaction between a series of N-diisopropyloxyphosphoryl dipeptides （or methyl esters） （DPP） and amino acids was studied by using electrospray ionization mass spectromewy （ESI- MS）. The results showed that aromatic rings formed π-π conjugated system could greatly strengthen the interaction, and the π-π stacking force was the most important non-covalent interaction force. Also, the polar groups generating hydrogen bonds were favourable to the complexes. But the form of hydrogen bonds would depend on the molecular flexibility. In addition, the molecule size and steric hindrance showed obvious effects on the interaction. While the chirality of amino acids had no effect on the interaction under ESI - MS conditions