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Synthesis of a cleavable heterobifunctional photolabelling reagent: Ring-labelled 3-[(4-azidophenyl)dithio]propionic acid-^(14)C

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. http://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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/jlcr.2580270805DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/jlcr.2580270805/abstractPublisherArticle
ORCID:
AuthorORCID
Tirrell, David A.0000-0003-3175-4596
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.
Funders:
Funding AgencyGrant Number
Center for University of Massachusetts-Industry Research on PolymersUNSPECIFIED
NSFUNSPECIFIED
Subject Keywords:3-[(4-azidophenyl)dithio]propionic acid; photolabelling reagent; biomembrane; synthesis; carbon-14
Record Number:CaltechAUTHORS:RAMjlcr1989
Persistent URL:http://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:25 Feb 2015 03:44

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