26971-98-2Relevant articles and documents
PHP-Tethered N-Acyl Carbamate: A Photocage for Nicotinamide
Salahi, Farbod,Purohit, Vatsal,Ferraudi, Guillermo,Stauffacher, Cynthia,Wiest, Olaf,Helquist, Paul
, p. 2547 - 2550 (2018/05/22)
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.
Development of carbamate-tethered coumarins as phototriggers for caged nicotinamide
Bourbon, Pauline,Peng, Qian,Ferraudi, Guillermo,Stauffacher, Cynthia,Wiest, Olaf,Helquist, Paul
supporting information, p. 6321 - 6324 (2013/11/19)
The syntheses of 7-diethylaminocoumarin- or modified DEACM-nicotinamide and 6-bromo-7-methoxycoumarin- or BMCM-nicotinamide have been accomplished by reaction of nicotinoyl isocyanate with the corresponding coumarin allylic alcohol derivatives. The resulting compounds contain an N-acyl O-alkyl carbamate as a new type of linkage for the caging of nicotinamide with a coumarin phototrigger, which undergoes cleavage upon photolysis. Our design of specific caged-nicotinamides was based upon NBO and TD-FT calculations to predict absorption wavelengths and photocleavage potential. This work provides a potentially general method for the caging of amides with coumarin photolabile protecting groups.
