Journal of Organic Chemistry p. 7135 - 7137 (1993)
Update date:2022-08-04
Topics:
Fleming, Steven A.
Jensen, Anton W.
The nucleoside transport inhibitor 6-<(4-nitrobenzyl)thio>-9-(β-D-ribofuranosyl)purine, NBMPR, has been used successfully in photoaffinity labeling.We have studied the mechanism for photocleavage of the benzyl-sulfur bond by using substituted benzyl phenyl sulfides as analogues of NBMPR.This has enabled us to enhance the photoreactivity of the benzyl-sulfur bond.We have also performed "radical clock" studies with a hexenyl side chain to trap reactive intermediates.The mechanistic interpretation from the substituent and side chain studies is that the benzyl-sulfur moiety is photocleaved via a homolytic pathway.
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Doi:10.1021/jo00078a023
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