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. 1965 Sep;96(3):577–582. doi: 10.1042/bj0960577

Relation between optical configuration and immunogenicity of synthetic polypeptides

F Borek 1, Yehudit Stupp 1, Sara Fuchs 1, M Sela 1
PMCID: PMC1207190  PMID: 5862399

Abstract

1. Three random linear copolymers composed of two or three of the amino acids d-tyrosine, d-glutamic acid, d-alanine and d-lysine, and a branched multichain copolymer with a poly-d-lysine backbone and polymeric side chains of d-tyrosine and d-glutamic acid, were found to be non-antigenic in rabbits, by precipitin and passive cutaneous anaphylaxis, and in guinea pigs, by delayed hypersensitivity tests. The corresponding four copolymers of l-amino acids were shown to be antigenic by all the three criteria. 2. No immunological cross-reactions were observed between the polypeptides composed of d-amino acids and the corresponding l-amino acid copolymers. 3. Similarly, an azobenzenearsonic acid conjugate of poly-d-tyrosine was shown to be non-antigenic in guinea pigs, in contrast with an analogous conjugate of poly-l-tyrosine. Animals sensitized with the conjugate of poly-l-tyrosine did not exhibit delayed skin reactions, when cross-tested with the d-conjugate. 4. A linear polymer composed of d-tyrosine, l-glutamic acid and l-alanine was found to be immunogenic and to cross-react with the corresponding polymer composed exclusively of d-amino acids.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. BEN-EFRAIM S., FUCHS S., SELA M. Hypersensitivity to a synthetic polypeptide: induction of a delayed reaction. Science. 1963 Mar 22;139(3560):1222–1223. doi: 10.1126/science.139.3560.1222. [DOI] [PubMed] [Google Scholar]
  2. BEN-EFRAIM S., FUCHS S., SELA M. PASSIVE CUTANEOUS ANAPHYLAXIS IN THE GUINEA-PIG WITH RABBIT ANTIBODIES AGAINST SYNTHETIC POLYPEPTIDES. Immunology. 1964 Mar;7:142–149. [PMC free article] [PubMed] [Google Scholar]
  3. BENACERRAF B., OJEDA A., MAURER P. H. STUDIES ON ARTIFICIAL ANTIGENS. II. THE ANTIGENICITY IN GUINEA PIGS OF ARSANILIC ACID CONJUGATES OF COPOLYMERS OF D- OR L-ALPHA-AMINO ACIDS. J Exp Med. 1963 Dec 1;118:945–952. doi: 10.1084/jem.118.6.945. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. GILL T. J., 3rd, GOULD H. J., DOTY P. Role of optical isomers in determining the antigenicity of synthetic polypeptides. Nature. 1963 Feb 23;197:746–747. doi: 10.1038/197746a0. [DOI] [PubMed] [Google Scholar]
  5. GILL T. J., 3rd, KUNZ H. W., GOULD H. J., DOTY P. STUDIES ON SYNTHETIC POLYPEPTIDE ANTIGENS. XI. THE ANTIGENICITY OF OPTICALLY ISOMERIC SYNTHETIC POLYPEPTIDES. J Biol Chem. 1964 Apr;239:1107–1113. [PubMed] [Google Scholar]
  6. LESKOWITZ S. Immunochemical study of antigenic specificity in delayed hypersensitivity. II. Delayed hypersensitivity to polytyrosine-azobenzenearsonate and its suppression by haptens. J Exp Med. 1963 Jun 1;117:909–923. doi: 10.1084/jem.117.6.909. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. LEVINE B. B. ANTIGENICITY OF HEPTEN CONJUGATES OF POLY-D-LYSINE AND OF POLY-L-LYSINE IN STRAIN 2 GUINEA PIGS. Nature. 1964 Jun 6;202:1008–1009. doi: 10.1038/2021008a0. [DOI] [PubMed] [Google Scholar]
  8. MAURER P. H. (ANTIGENICITY OF POLYPEPTIDES (POLY-ALPHA-AMINO ACIDS). IV. STUDIES IN GUINEA PIGS. J Immunol. 1963 Apr;90:493–505. [PubMed] [Google Scholar]
  9. MAURER P. H. Antigenicity of polypeptides (poly alpha amino acids). X. Studies with polymers of D amino acids. Proc Soc Exp Biol Med. 1963 Jul;113:553–557. doi: 10.3181/00379727-113-28423. [DOI] [PubMed] [Google Scholar]
  10. MAURER P. H., CASHMAN T. ANTIGENICITY OF POLYPEPTIDES (POLY-ALPHA-AMINO ACIDS). VIII. STUDIES IN GUINEA PIGS. J Immunol. 1963 Mar;90:393–398. [PubMed] [Google Scholar]
  11. OUCHTERLONY O. Diffusion-in-gel methods for immunological analysis. Prog Allergy. 1958;5:1–78. [PubMed] [Google Scholar]
  12. SAGE H. J., DEUTSCH G. F., FASMAN G. D., LEVINE L. THE SEROLOGICAL SPECIFICITY OF THE POLY-ALANINE IMMUNE SYSTEM. Immunochemistry. 1964 Jun;1:133–144. doi: 10.1016/0019-2791(64)90077-1. [DOI] [PubMed] [Google Scholar]
  13. SELA M., ARNON R. Studies on the chemical basis of the antigenicity of proteins. 1. Antigenicity of polypeptidyl gelatins. Biochem J. 1960 Apr;75:91–102. doi: 10.1042/bj0750091. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. SELA M., FUCHS S., ARNON R. Studies on the chemical basis of the antigenicity of proteins. 5. Synthesis, characterization and immunogenicity of some multichain and linear polypeptides containing tyrosine. Biochem J. 1962 Oct;85:223–235. doi: 10.1042/bj0850223. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. TABACHNICK M., SOBOTKA H. Azoproteins. II. A spectrophotometric study of the coupling of diazotized arsanilic acid with proteins. J Biol Chem. 1960 Apr;235:1051–1054. [PubMed] [Google Scholar]

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