The role of deltorphin II phenylalanine residue in binding to the δ opioid receptor

T. Honda, N. Shirasu, Y. Chuman, K. Okada, T. Fujita, Takeru Nose, Y. Shimohigashi

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Abstract

Deltorphin II is a peptide ligand specific for the δ opioid receptor. In order to elucidate the role of Phe3 in binding to the δ opioid receptor, we synthesized a series of analogs in which Phe3 was replaced by various amino acids such as Ala, cyclohexylalanine (Cha), fluorophenylalanines, and other alkyl-side chain amino acids (Val, Leu, and norleucine (Nle)). It was found that [Cha3]deltorphin II and [Nle3]deltorphin II retain almost a full receptor binding affinity. The results indicated that the Phe3-phenyl group of deltorphin II can be substituted by the alkyl groups Such as cyclohexyl and propyl in the interaction with the δ receptor.

Original languageEnglish
Pages (from-to)2549-2552
Number of pages4
JournalBulletin of the Chemical Society of Japan
Volume73
Issue number11
DOIs
Publication statusPublished - Nov 1 2000

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Opioid Receptors
Phenylalanine
Norleucine
Amino Acids
Ligands
Peptides
Ala(2)-deltorphin II

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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The role of deltorphin II phenylalanine residue in binding to the δ opioid receptor. / Honda, T.; Shirasu, N.; Chuman, Y.; Okada, K.; Fujita, T.; Nose, Takeru; Shimohigashi, Y.

In: Bulletin of the Chemical Society of Japan, Vol. 73, No. 11, 01.11.2000, p. 2549-2552.

Research output: Contribution to journalArticle

Honda, T, Shirasu, N, Chuman, Y, Okada, K, Fujita, T, Nose, T & Shimohigashi, Y 2000, 'The role of deltorphin II phenylalanine residue in binding to the δ opioid receptor', Bulletin of the Chemical Society of Japan, vol. 73, no. 11, pp. 2549-2552. https://doi.org/10.1246/bcsj.73.2549
Honda, T. ; Shirasu, N. ; Chuman, Y. ; Okada, K. ; Fujita, T. ; Nose, Takeru ; Shimohigashi, Y. / The role of deltorphin II phenylalanine residue in binding to the δ opioid receptor. In: Bulletin of the Chemical Society of Japan. 2000 ; Vol. 73, No. 11. pp. 2549-2552.
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AU - Nose, Takeru

AU - Shimohigashi, Y.

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