Photocleavage of Benzyl-Sulfide Bonds

Steven A. Fleming, Anton W. Jensen

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)7135-7137
Number of pages3
JournalJournal of Organic Chemistry
Volume58
Issue number25
DOIs
StatePublished - 1993

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