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PHP-Tethered N-Acyl Carbamate: A Photocage for Nicotinamide.

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 ? = 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.

SUBMITTER: Salahi F

PROVIDER: S-EPMC6593154 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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pHP-Tethered N-Acyl Carbamate: A Photocage for Nicotinamide.

Salahi Farbod F Purohit Vatsal V Ferraudi Guillermo G Stauffacher Cynthia C Wiest Olaf O Helquist Paul P

Organic letters 20180413 9

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 y ...[more]

PMID: 29652162

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