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TAPP analogs containing β 3 ‐ homo ‐amino acids: synthesis and receptor binding
Author(s) -
Podwysocka D.,
Kosson P.,
Lipkowski A. W.,
Olma A.
Publication year - 2012
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.2433
Subject(s) - tetrapeptide , peptidomimetic , chemistry , amino acid , stereochemistry , receptor , peptide , opioid peptide , opioid , opioid receptor , biochemistry
β‐Amino acids containing α,β‐hybrid peptides show great potential as peptidomimetics. In this paper, we describe the synthesis and affinity to μ‐opioid and δ‐opioid receptors of α,β‐hybrids, analogs of the tetrapeptide Tyr‐ d ‐Ala‐Phe‐Phe‐NH 2 (TAPP). Each amino acid was replaced with an l ‐ or d ‐β 3 ‐ h ‐amino acid. All α,β‐hybrids of TAPP analogs were synthesized in solution and tested for affinity to μ‐opioid and δ‐opioid receptors. The analog Tyr‐β 3 h ‐ d ‐Ala‐Phe‐PheNH 2 was found to be as active as the native tetrapeptide. Copyright © 2012 European Peptide Society and John Wiley & Sons, Ltd.