Photochemistry of nucleoside transport inhibitor 6-S-benzylated thiopurine ribonucleosides. Implications for a new class of photoaffinity labels

SA Fleming, DB Rawlins, V Samano…

Index: Fleming, Steven A.; Rawlins, David B.; Samano, Vicente; Robins, Morris J. Journal of Organic Chemistry, 1992 , vol. 57, # 22 p. 5968 - 5976

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Citation Number: 13

Abstract

Photochemistq of the nucleoside transport inhibitor 6-[(4-nitrobenzyl) thio]-BGB- Dribofuranosyl) p~ e (NBMPR, 1) yielded products from the initial homolytic cleavage of the benzyl-sulfur bond. Photoreduction of the nitro group also occurred to a minor extent. The quantum yield for the disappearance of 1 wa8-0.04. Several photoproducts and secondary photoproducts were identified and confirmed by synthesis. Irradiation of 6-(benzylthio)-g-( ...