TAPP analogs containing β3 -homo-amino acids: synthesis and receptor binding.
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.
Institute of Organic Chemistry, Lodz University of Technology, Lodz, Poland.
D
D
Podwysocka
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P
Kosson
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AW
Lipkowski
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A
Olma
D000596:Amino Acids / Q000737:chemistry*; D009842:Oligopeptides / Q000737:chemistry*; D018847:Opioid Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D011485:Protein Binding; D011957:Receptors, Opioid / Q000378:metabolism*
D000596:Amino Acids; D009842:Oligopeptides; D018847:Opioid Peptides; D011957:Receptors, Opioid; C103476:tyrosyl-alanyl-phenylalanyl-phenylalaninamide