Libraries of opiate and anti-opiate peptidomimetics containing 2,3-methanoleucine.

@article{Burgess1997LibrariesOO,
  title={Libraries of opiate and anti-opiate peptidomimetics containing 2,3-methanoleucine.},
  author={K. Burgess and W. Li and D. Linthicum and Q. Ni and D. Pledger and R. Rothman and A. Shitangkoon},
  journal={Bioorganic \& medicinal chemistry},
  year={1997},
  volume={5 9},
  pages={
          1867-71
        }
}
A library of 96 peptides/peptidomimetics was prepared, in which half was based on the YGGFL-NH2 sequence, while the remainder were derivatives of a presumed anti-opiate peptide, YGGFLRF-NH2. Of the 48 compounds in each half of the library, 32 contained a stereoisomer of 2,3-methanoleucine substituted for Leu5. Binding of the YGGFL-NH2 derivatives to the mu- and delta-opioid receptors, and to the anti-beta-endorphin monoclonal antibody (clone 3E7), indicated any change at the Leu5 had little… Expand
7 Citations
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References

SHOWING 1-10 OF 16 REFERENCES
Enhanced antiopiate activity and enzyme resistance in a peptidomimetic of FMRFamide containing E-2,3-methanomethionine and E-2,3-methanophenylalanine
TLDR
The effect on antiopiate potency of an additional rigid substitution of FMRFamide containing methanomethionine alone was determined, and the increased potency appears to be related to enzyme resistance rather than receptor affinity. Expand
Systematic study of substance P analogs. II. Rapid screening of 512 substance P stereoisomers for binding to NK1 receptor.
TLDR
A model study of large scale screening of stereoisomers of substance P with systematic D-amino acid replacements suggests a largely additive binding activity of SP from each residue on binding to central NK1 receptors. Expand
Enhanced antiopiate activity and enzyme resistance in peptidomimetics of FMRFamide containing (E)-2,3-methanomethionine
TLDR
Although both peptidomimetics bound with lower affinity than FMRFamide to rat spinal cord receptors for NPFF (the mammalian F MRFamide-like peptide), they were far more resistant to enzymatic degradation by leucine aminopeptidase. Expand
Enhanced antiopiate activity in peptidomimetics of FMRFamide containing Z-2,3-methanomethionine
TLDR
The current study determined the antiopiate potency of FMRFa and two conformationally constrained peptidomimetics of F MRFa containing stereoisomers of Z-2,3-methanomethionine, which bound with lower affinity to rat spinal cord receptors for the mammalian FMR Fa-like peptide, NPFF. Expand
Enzyme inhibition by dipeptides containing 2,3‐methanophenylalanine, a sterically constrained amino acid
TLDR
Both (2R,3S)‐ and (2S,3R)‐▽EPhe‐Phe(or Leu)‐OMe were found to inhibit effectively the hydrolysis of Ac‐Tyr‐OEt by chymotrypsin in a competitive manner. Expand
Enkephalin-related peptides: Direct action on the octopus heart
TLDR
Systemic hearts of Octopus vulgaris were perfused with sea wate and test substances and a crude extract of vena cave were added for 1 min; frequency and pressure were monitored continuously, and naloxone treatment had no effect. Expand
Low affinity of FMRFamide and four FaRPs (FMRFamide-related peptides), including the mammalian-derived FaRPs F-8-Famide (NPFF) and A-18-Famide, for opioid μ, δ, κ1 , κ2a , or κ2b receptors
TLDR
The known ability of FMRFamide and FaRPs to interact with the opioid system does not appear to be related to direct binding to these opioid receptors. Expand
The synthesis, bioactivity and enzyme stability of D-Ala2, EPhe4, Leu5-enkephalins.
TLDR
The first enkephalin analog containing a "cyclopropyl" phenylalanine (Phe) residue is synthesized, which is apparently responsible for its low activity in the MVD and GPI muscle assays. Expand
Production and characterization of monoclonal idiotypes and anti-idiotypes for small ligands.
TLDR
Several different types of immunoassays are developed which afford greater flexibility to the investigator, depending on the type of antibodies desired and the availability of labeled antigens, to identify and characterize monoclonal antibodies and their respective anti-idiotypes. Expand
Solid Phase Peptide Synthesis
Abstract The last two decades have been an era of rapid progress in peptide research. This era was begun by the work of Sanger on the amino acid sequence determination of insulin and by du VigneaudExpand
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