Ramaswami, Varadarajan and Tirrell, David A. (1989) Synthesis of a cleavable heterobifunctional photolabelling reagent: Ring-labelled 3-[(4-azidophenyl)dithio]propionic acid-^(14)C. Journal of Labelled Compounds and Radiopharmaceuticals, 27 (8). pp. 889-899. ISSN 0362-4803. doi:10.1002/jlcr.2580270805. https://resolver.caltech.edu/CaltechAUTHORS:RAMjlcr1989
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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.
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| 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. | |||||||||
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| Subject Keywords: | 3-[(4-azidophenyl)dithio]propionic acid; photolabelling reagent; biomembrane; synthesis; carbon-14 | |||||||||
| Issue or Number: | 8 | |||||||||
| DOI: | 10.1002/jlcr.2580270805 | |||||||||
| Record Number: | CaltechAUTHORS:RAMjlcr1989 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:RAMjlcr1989 | |||||||||
| Official Citation: | Ramaswami, V. and Tirrell, D. A. (1989), Synthesis of a cleavable heterobifunctional photolabelling reagent: Ring-labelled 3-[(4-azidophenyl)dithio]propionic acid-14C. J Label Compd Radiopharm, 27: 889–899. doi: 10.1002/jlcr.2580270805 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 54592 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Anne Hormann | |||||||||
| Deposited On: | 25 Feb 2015 03:44 | |||||||||
| Last Modified: | 10 Nov 2021 20:35 |
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