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(4-Carboxamido)phenylalanine is a surrogate for tyrosine in opioid receptor peptide ligands.

Abstract：

:(S)-4-(Carboxamido)phenylalanine (Cpa) is examined as a bioisosteric replacement for the terminal tyrosine (Tyr) residue in a variety of known peptide ligands for the mu, delta and kappa opioid receptors. The Cpa-containing peptides, assayed against cloned human opioid receptors, display comparable binding affinity (Ki), and agonist potency (EC50) to the parent ligands at the three receptors. Cpa analogs of delta selective peptides show an increase in delta selectivity relative to the mu receptor. Cpa is the first example of an amino acid that acts as a surrogate for Tyr in opioid peptide ligands, challenging the long-standing belief that a phenolic residue is required for high affinity binding.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Dolle RE,Machaut M,Martinez-Teipel B,Belanger S,Cassel JA,Stabley GJ,Graczyk TM,DeHaven RN

doi

10.1016/j.bmcl.2004.04.039

subject

Has Abstract

pub_date

2004-07-05 00:00:00

pages

3545-8

issue

13

eissn

0960-894X

issn

1464-3405

pii

S0960894X04005293

journal_volume

14

pub_type

杂志文章

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