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Published February 1986 | public
Journal Article

Photolabeling studies of polymer–cell surface interaction. Evaluation of 3-[(4-azidophenyl)dithio]propionic acid as a polymer-bound photolabel

Abstract

3-[(4-Azidophenyl)dithio]propionic acid (1a) was prepared in four steps from 4,4′-diamino-diphenyldisulfide. Attachment of 1a to poly[(3-hydroxypropyl)oxirane] was accomplished under very mild conditions via an acid-catalyzed caarbodiimide coupling. Photolysis of polymer-bound 1a with an electronic flash unit proceeded without detectable disulfide bond cleavage. Mild reduction of the disulfide bond of an analogue of 1a which carried no azido group confirmed that 1a should be useful in photolabeling studies of polymer–cell surface interaction.

Additional Information

Copyright © 1986 John Wiley & Sons, Inc. Received May 14, 1985; Accepted June 24, 1985. This work was supported in part by the Center for University of Massachusetts-Industry Research on Polymers. Support for our research programs by the Alfred P. Sloan Foundation (Research Fellowship to D.A.T.) and by a Presidential Young Investigator Award of the National Science Foundation (to D.A.T.) is also gratefully acknowledged. Fourier transform infrared spectra were recorded in the laboratory of S. L. Hsu and ultraviolet spectra in the laboratory of T. J. McCarthy. Part 10 in a series on "Interactions of Synthetic Polymers with Cell Membranes and Model Membrane Systems."

Additional details

Created:
August 19, 2023
Modified:
October 20, 2023