一种新的氨基酸、杂合肽和 BODIPY 类似物：2-氨基托酰-L-丙氨酸 (ATA) 衍生物的合成和评价,Organic & Biomolecular Chemistry

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一种新的氨基酸、杂合肽和 BODIPY 类似物：2-氨基托酰-L-丙氨酸 (ATA) 衍生物的合成和评价
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2022-11-11 , DOI: 10.1039/d2ob01905a
Manish K Gupta _{1,

2} , Nagendra K Sharma _{1,

2}

Affiliation

由于 π 相互作用，天然芳香族 α-氨基酸残基在蛋白质的结构和功能组织中起着关键作用。它们的芳香族残基来源于苯类支架。非苯类芳香支架如托酮和托酚酮也是托酚类天然产物的成分。托酚酮还具有显示 π 相互作用以及额外氢键的能力。因此，包含丙酰基的氨基酸可能是新型拟肽的潜在组成部分。本报告描述了L -氨基托苯丙氨酸氨基酸 ( ATA) 及其与肽偶联剂 EDC 的不寻常活性。重要的是，由于丙酰残基，其二肽在有机溶剂中形成 β-折叠/-转角型二级结构。这种氨基酸是合成荧光氨基酸（如 BODIPY 氨基酸类似物）的极佳支架。然而，这种氨基酸及其 BODIPY 衍生物可以在低浓度（~50 μM）下进入 HeLa 细胞而不会表现出显着的细胞毒性。因此，ATA及其 BODIPY 衍生物是很有前途的芳香族氨基酸，可用于构建潜在的拟肽和目标肽的荧光标记。

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A new amino acid, hybrid peptides and BODIPY analogs: synthesis and evaluation of 2-aminotroponyl-L-alanine (ATA) derivatives

Natural aromatic α-amino acid residues play critical roles in the structural and functional organization of proteins owing to π-interactions. Their aromatic residues are derived from benzenoid scaffolds. Non-benzenoid aromatic scaffolds such as tropone and tropolone are also constituents of troponoid natural products. Tropolone has also the ability to exhibit π-interactions along with additional hydrogen bonding. Thus, amino acids comprising troponyl could be potential building blocks of novel peptidomimetics. This report describes the synthesis of the L-aminotroponylalanine amino acid (ATA) and its unusual activity with the peptide coupling agent EDC. Importantly, its di-peptides form β-sheet/-turn type secondary structures in organic solvents owing to the troponyl residue. This amino acid is an excellent scaffold for the synthesis of fluorescent amino acids such as BODIPY amino acid analogs. Nevertheless, this amino acid and its BODIPY derivatives can enter HeLa cells without exhibiting significant cytotoxicity at low concentrations (∼50 μM). Hence, ATA and its BODIPY derivatives are promising aromatic amino acids for the construction of potential peptidomimetics and fluorescent labelling of target peptides.

更新日期：2022-11-11

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