The Journal of Experimental Medicine
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The Journal of Experimental Medicine, Vol 136, 387-391, Copyright © 1972 by The Rockefeller University Press

BRIEF DEFINITIVE REPORTS

ANTIGEN RECOGNITION AND THE IMMUNE RESPONSE : STRUCTURAL REQUIREMENTS IN THE SIDE CHAIN OF TYROSINE FOR IMMUNOGENICITY OF L-TYROSINE-AZOBENZENEARSONATE



Sefik S. Alkan 1, Maurice E. Bush 1, Danute E. Nitecki 1, and Joel W. Goodman 1

1 From the Department of Microbiology, University of California, San Francisco, San Francisco, California 94122

The low molecular weight compound L-tyrosine-azobenzenearsonate (RAT) induces a cellular immune response in guinea pigs. The contribution of the side chain of tyrosine to the immunogenicity of RAT and the structural requirements at that position for immunogenicity were assessed by synthesizing a series of analogs of RAT containing modifications in the side chain of tyrosine and employing them as immunogens. Removal of either the carboxyl or amino group did not markedly affect immunogenicity, measured by the induction of delayed cutaneous sensitivity, whereas deletion of both completely abolished it. However, a charged group was not required since side chains containing a polar hydroxyl group could substitute for chains bearing an amino or carboxyl group. The size of the side chain exerted a pronounced influence; the charged or polar substituent had to be extended from the phenolic ring by at least two carbon atoms in order to confer immunogenicity.

Submitted on May 25, 1972


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