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Synthesis of a cleavable heterobifunctional photolabelling reagent: Ring‐labelled 3‐[(4‐azidophenyl)dithio]propionic acid‐ 14 C
Author(s) -
Ramaswami Varadarajan,
Tirrell David A.
Publication year - 1989
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580270805
Subject(s) - chemistry , phthalimide , reagent , ring (chemistry) , acetanilide , yield (engineering) , disulfide bond , hydrolysis , medicinal chemistry , organic chemistry , combinatorial chemistry , biochemistry , materials science , metallurgy
An efficient synthesis of ring‐labelled 3‐[(4‐azidophenyl)dithio]propionic acid‐ 14 C is described. Chlorosulfonation of uniformly ring‐labelled acetanilide‐ 14 C followed by reductive dimerization of the sulfonyl chloride with HI afforded 4‐acetamidophenyl disulfide. Hydrolysis and diazotization then gave 4‐azidophenyl disulfide, which was converted to the title compound via the sulfur transfer reagent N‐(4‐azidophenylthio)phthalimide. The overall yield of 3‐[(4‐azidophenyl)dithio]propionic acid‐ 14 C was 22%. 3‐[(4‐Azidophenyl)dithio]propionic acid‐ 14 C is a cleavable heterobifunctional photolabelling reagent of potential utility in studies of biomembrane structure and intermacromolecular interaction.