From MonoBINOL to BisBINOL: Expanded Enantioselective Fluorescent Recognition of Amino Acids
From MonoBINOL to BisBINOL: Expanded Enantioselective Fluorescent Recognition of Amino Acids
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DOI：
10.1021/acs.joc.1c00507
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发表时间：
2021-04-26
影响因子：
3.6
通讯作者：
Pu, Lin
中科院分区：
文献类型：
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作者：
Huo, Bingyi;Lu, Kai;Pu, Lin
甲氧基甲基保护的(R)-3,3'-二甲酰-1,1'-双-2-萘酚（BINOL）与（吡啶-2,6-二基双（亚甲基））双（三苯基磷）二溴在碱存在下缩合，然后脱保护，得到了新的双BINOL基荧光探针（R，R）-4。该化合物对17种常见氨基酸具有良好的对映选择性荧光反应，对氨基酸识别的底物范围扩大。以（R，R）-4与L-和d -缬氨酸缩合为原料合成了两种非对映异构体亚胺，并利用各种光谱方法研究了这些亚胺与Zn(OAc)(2)的反应，以便更好地了解对映选择性荧光识别过程。
Condensation of the methoxymethyl-protected (R)-3,3'-diformyl-1,1'-bi-2-naphthol (BINOL) with (pyridine-2,6-diylbis(methylene))bis(triphenyl phosphonium)dibromide in the presence of a base followed by deprotection gave a new bisBINOL-based fluorescent probe (R,R)-4. This compound showed expanded substrate scope in the recognition of amino acids with good enantioselective fluorescence responses toward 17 common amino acids. Two diastereomeric imines were synthesized from the condensation of (R,R)-4 with L- and D-valine, and the reactions of these imines with Zn(OAc)(2) were investigated by various spectroscopic methods for a better understanding of the enantioselective fluorescent recognition process.