Published August 1989
| public
Journal Article
Synthesis of a cleavable heterobifunctional photolabelling reagent: Ring-labelled 3-[(4-azidophenyl)dithio]propionic acid-^(14)C
- Creators
- Ramaswami, Varadarajan
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Tirrell, David A.
Abstract
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.
Additional Information
© 1989 John Wiley & Sons. This work was supported by the Center for University of Massachusetts-Industry Research on Polymers. Support of our research programs by a Presidential Young Investigator Award of the National Science Foundation (to D.A.T.) is also acknowledged. NMR spectra were recorded in the University of Massachusetts NMR Laboratory, which is supported in part by the NSF Materials Research Laboratory at the University.Additional details
- Eprint ID
- 54592
- DOI
- 10.1002/jlcr.2580270805
- Resolver ID
- CaltechAUTHORS:RAMjlcr1989
- Center for University of Massachusetts-Industry Research on Polymers
- NSF
- Created
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2015-02-25Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field