Dipartimento di Biotecnologie, Chimica e Farmacia, Università degli Studi di Siena, Via Aldo Moro 2, 53100, Siena, Italy.
Istituto di Scienze e Tecnologie Chimiche "G. Natta" - SCITEC (CNR), Via A. Corti 12, 20133, Milano, Italy.
Chem Asian J. 2024 Oct 16;19(20):e202400617. doi: 10.1002/asia.202400617. Epub 2024 Sep 21.
The reactivity of Morita-Baylis-Hillman Adduct (MBHA) derivative 7 was studied with different primary amine derivatives such as n-butylamine, Nα-acetyl-L-lysine methyl ester, and a poly-(L-lysine) derivative as lysine models to obtain information about the possible reactions in complex protein environments. MBHA derivative 7 reacted with n-butylamine or Nα-acetyl-L-lysine methyl ester producing monoadducts 9a or 9c, which showed bright emission features in the green region at 526-535 nm with photoluminescence quantum yield values in solutions of 73 % and 51 %, respectively. Based on these results, MBHA derivative 7 can be considered an interesting new fluorogenic probe potentially useful in the labelling of basic amino acid residues. Furthermore, similar to other MBHA derivatives, compound 7 showed the tendency to produce diadducts especially in polar solvents system where specific interactions between the extended aromatic moieties may play a major role.
研究了 Morita-Baylis-Hillman 加合物（MBHA）衍生物 7 与不同伯胺衍生物（如正丁胺、Nα-乙酰-L-赖氨酸甲酯和聚（L-赖氨酸）衍生物）的反应活性，这些伯胺衍生物作为赖氨酸模型，以获取有关在复杂蛋白质环境中可能发生的反应的信息。MBHA 衍生物 7 与正丁胺或 Nα-乙酰-L-赖氨酸甲酯反应生成单加合物 9a 或 9c，它们在绿色区域 526-535nm 处显示出明亮的发射特征，在溶液中的光致发光量子产率值分别为 73%和 51%。基于这些结果，可以认为 MBHA 衍生物 7 是一种有趣的新荧光探针，可能在碱性氨基酸残基的标记中有用。此外，与其他 MBHA 衍生物类似，化合物 7 表现出形成二加合物的趋势，特别是在极性溶剂体系中，其中扩展的芳族部分之间的特定相互作用可能起主要作用。
