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

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.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Carbamates / chemistry*
  • Molecular Structure
  • Niacin
  • Niacinamide

Substances

  • Carbamates
  • Niacinamide
  • Niacin