Photochemistry of. alpha.-keto phosphate esters: photorelease of a caged cAMP.

…, PS Athey, LW Kueper III, B Matuszewski…

Index: Givens, Richard S.; Athey, Phillip S.; Kueper III, L. William; Matuszewski, Bogdan; Xue, Jie-You Journal of the American Chemical Society, 1992 , vol. 114, # 22 p. 8708 - 8710

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Citation Number: 73

Abstract

Study of the subsequent biological process is hampered, however, by two inconvenient features of o-nitrobenzyl photochemistry:(1) the release of the phosphate occurs by a slow, rate-limiting hydrolysis (k,= lo2 sl) of the aci-nitro intermediate 2, & and (2) the nitrosophenyl ketone 3 is not biologically inert. 4f Earlier we reported5 that benzoin diethyl phosphate (4a) is efficiently converted to 2-phenylbenzo [b] furan upon photolysis in methanol, acetonitrile ...