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N-Acylation of stimulatory amino acids changes chiral recognition of the fleshfly labellar sugar receptor

Summary

N-Acylation changed nonstimulatory Dvaline into a clear stimulant of the sugar receptor of the fleshfly,Boettcherisca peregrina. Of theN-acyl-D-valines, the most stimulatory wasN-acetyl-D-valine. Similar changes into stimulants were also observed in other aliphatic amino acids such as leucine and methionine. Dose-response curves ofN-acetyl-D-valine suggested an increase of binding affinity, compared with that ofN-acetyl-L-valine. By treatment experiment with pronase 10 mg/ml, stimulatoryN-acetyl-D-amino acids were suggested to react with the specific alkyl site (R site), which was presumed to discriminate between L- and D-forms of the amino acids through steric hindrance between its own spatial barrier and D-amino acids (Shimada and Isono 1978; Shimada and Tanimura 1981).

This change of chiral recognition cannot be explained by simple steric hindrance at the R site. It means, instead, that a hydrophobic subsite rather than a spatial barrier must be postulated.

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Shimada, I., Maki, Y. & Sugiyama, H. N-Acylation of stimulatory amino acids changes chiral recognition of the fleshfly labellar sugar receptor. J. Comp. Physiol. 165, 193–196 (1989). https://doi.org/10.1007/BF00619193

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Keywords

  • Taste Receptor
  • Sweet Taste
  • Chiral Recognition
  • Aliphatic Amino Acid
  • Sugar Receptor