pH 依赖性酰胺键：烟酰胺的光笼。
pHP-Tethered N-Acyl Carbamate: A Photocage for Nicotinamide.
机构信息
Department of Chemistry and Biochemistry , University of Notre Dame , Notre Dame , Indiana 46556 , United States.
Department of Biological Sciences , Purdue University , 915 West State Street , West Lafayette , Indiana 47907 , United States.
出版信息
Org Lett. 2018 May 4;20(9):2547-2550. doi: 10.1021/acs.orglett.8b00697. Epub 2018 Apr 13.
Abstract
The synthesis of a new photocaged nicotinamide having an N-acyl carbamate linker and a p-hydroxyphenacyl (pHP) chromophore is described. The photophysical and photochemical studies showed an absorption maximum at λ = 330 nm and a quantum yield for release of 11% that are dependent upon both pH and solvent. While the acyl carbamate releases nicotinamide efficiently, a simpler amide linker was inert to photocleavage. This photocaged nicotinamide has significant advantages with respect to quantum yield, absorbance wavelength, rate of release, and solubility that make it the first practical example of a photocaged amide.
摘要
描述了一种具有 N-酰基氨基甲酸酯连接基和对羟基苯乙酰基（pHP）生色团的新型光笼化烟酰胺的合成。光物理和光化学研究表明，吸收最大值为 λ = 330nm，释放量子产率为 11%，这取决于 pH 值和溶剂。虽然酰氨基甲酸酯有效地释放烟酰胺，但更简单的酰胺连接基对光裂解无反应。这种光笼化烟酰胺在量子产率、吸收波长、释放速率和溶解度方面具有显著优势，使其成为第一个实用的光笼化酰胺的实例。
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