Abstract：
:Endogenous opioid peptides consist of a conserved amino acid residue of Phe(3) and Phe(4), although their binding modes for opioid receptors have not been elucidated in detail. Endomorphin-2, which is highly selective and specific for the mu opioid receptor, possesses two Phe residues at the consecutive positions 3 and 4. In order to clarify the role of Phe(3) and Phe(4) in binding to the mu receptor, we synthesized a series of analogs in which Phe(3) and Phe(4) were replaced by various amino acids. It was found that the aromaticity of the Phe-beta-phenyl groups of Phe(3) and Phe(4) is a principal determinant of how strongly it binds to the receptor, although better molecular hydrophobicity reinforces the activity. The receptor binding subsites of Phe(3) and Phe(4) of endomorphin-2 were found to exhibit different structural requirements. The results suggest that [Trp(3)]endomorphin-2 (native endomorphin-1) and endomorphin-2 bind to different receptor subclasses.
journal_name
Bioorg Med Chemjournal_title
Bioorganic & medicinal chemistryauthors
Honda T,Shirasu N,Isozaki K,Kawano M,Shigehiro D,Chuman Y,Fujita T,Nose T,Shimohigashi Ydoi
10.1016/j.bmc.2007.03.009subject
Has Abstractpub_date
2007-06-01 00:00:00pages
3883-8issue
11eissn
0968-0896issn
1464-3391pii
S0968-0896(07)00195-2journal_volume
15pub_type
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