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The synthesis of a peptide having the structure attributed to a sound habituating material

  • Specialia Chimica, Biochimica
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Summary

A peptide isolated from rats habituated to a sound stimulus has been given the structure Glu-Ala-Gly-Tyr-Ser-Lys-OH. A synthesis of this compound afforded a product that different from the natural material on the basis of chromatographic and physiological comparisons. The proposed sequence must therefore be in error.

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Literatur

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  12. Since the free N6-amino group in lysine will routinely give a positive ninhydrin reaction, then the natural peptide must possess blocking groups at both the glutamic acid and lysine residues.

  13. After this work was completed, a second synthesis appeared:H. Lackner andN. Tiemann, Naturwissenschaften61, 217 (1974). Although the product possessed a broader mp of 170–177°, the chromatographic properties were said to be identical with our peptide. Unfortunately, a direct comparison was not possible between the Seattle and Göttingen peptides, due to a lack of additional material from the latter group. In any event, little biological activity was found and it was concluded that a mistake existed in the original structural investigation.

  14. G. Ungar, personal communication (June 5, 1975). The possible presence of some cofactor has been suggested as an explanation for the higher activity of the natural product.

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Authors and Affiliations

  1. Department of Chemistry BG-10, University of Washington, 98195, Seattle, Washington, USA

    B. Weinstein, R. M. Bartschot, R. M. Cook, P. S. Tam & H. N. Guttman

  2. Department of Biological Sciences, University of Illinois at Chicago Circle, 60680, Chicago, Illinois, USA

    B. Weinstein, R. M. Bartschot, R. M. Cook, P. S. Tam & H. N. Guttman

Authors
  1. B. Weinstein
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  2. R. M. Bartschot
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  3. R. M. Cook
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  4. P. S. Tam
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  5. H. N. Guttman
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Weinstein, B., Bartschot, R.M., Cook, R.M. et al. The synthesis of a peptide having the structure attributed to a sound habituating material. Experientia 31, 754–756 (1975). https://doi.org/10.1007/BF01938442

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  • DOI: https://doi.org/10.1007/BF01938442

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