Photolabile precursors of cyclic nucleotides with high aqueous solubility and stability.
Photolabile phosphotriester derivatives of cyclic AMP and cyclic GMP are described, where the additional group on the phosphate is a 2-nitrobenzyl that bears an electron-withdrawing and dianionic substituent. This confers high aqueous solubility and excellent resistance to hydrolysis of the phosphotriester (t(1/2) for hydrolysis at pH 7, 22 degrees C, is >3 months for the axial isomers 3a and 4a and >1 month for the equatorial isomers 3b and 4b). The photolysis quantum yields are in the range 0.15-0.24, and the product release rate upon flash photolysis is 1.7 s(-1) at pH 7.0, 20 degrees C.
Wang
Lijuan
L
Department of Biomedical Sciences, College of Veterinary Medicine, Cornell University, Ithaca, New York 14853, USA.
Corrie
John E T
JE
Wootton
John F
JF
D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D000242:Cyclic AMP / Q000031:analogs & derivatives* / Q000737:chemistry*; D006152:Cyclic GMP / Q000031:analogs & derivatives* / Q000737:chemistry*; D003500:Cyclization; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D009711:Nucleotides / Q000737:chemistry*; D010777:Photochemistry; D013696:Temperature
D009711:Nucleotides; D000242:Cyclic AMP; D006152:Cyclic GMP