Crystal structure of biphalin sulfate

A multireceptor opioid peptide

J. L. Flippen-Anderson, J. R. Deschamps, C. George, Victor J Hruby, A. Misicka, A. W. Lipkowski

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Biphalin is a dimeric opioid peptide, composed of two tetrapeptides connected 'tail-to-tail', that exhibits a high affinity for all three opioid receptor types (i.e. μ, δ and κ). This study presents the X-ray crystal structure of biphalin sulfate and compares it to other opioids that interact with the same biological targets. Both halves of the molecule have a folded backbone conformation but differ significantly from one another. Residues 1-4 in biphalin, which compare well with the δ selective opioid peptide DADLE, fold into a random coil. Residues 5-8, which can be fit to the μ selective peptide D-TIPP-NH2, exhibit a fairly normal type III′ β bend. Biphalin also exhibits structural similarities with two naltrexone analogs, naltrexonazine and norbinaltorphamine, that are specific to μ and κ receptor sites.

Original languageEnglish (US)
Pages (from-to)123-133
Number of pages11
JournalJournal of Peptide Research
Volume59
Issue number3
DOIs
StatePublished - 2002

Fingerprint

Opioid Peptides
Sulfates
Crystal structure
Leucine-2-Alanine Enkephalin
Naltrexone
Opioid Receptors
Opioid Analgesics
Conformations
X-Rays
X rays
Peptides
Molecules
biphalin

Keywords

  • Agonist
  • Analgesic
  • Biphalin
  • Conformation
  • Neuropeptide
  • Opioid receptor ligand
  • X-ray diffraction

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology

Cite this

Flippen-Anderson, J. L., Deschamps, J. R., George, C., Hruby, V. J., Misicka, A., & Lipkowski, A. W. (2002). Crystal structure of biphalin sulfate: A multireceptor opioid peptide. Journal of Peptide Research, 59(3), 123-133. https://doi.org/10.1046/j.1397-002x.2001.10967.x

Crystal structure of biphalin sulfate : A multireceptor opioid peptide. / Flippen-Anderson, J. L.; Deschamps, J. R.; George, C.; Hruby, Victor J; Misicka, A.; Lipkowski, A. W.

In: Journal of Peptide Research, Vol. 59, No. 3, 2002, p. 123-133.

Research output: Contribution to journalArticle

Flippen-Anderson, JL, Deschamps, JR, George, C, Hruby, VJ, Misicka, A & Lipkowski, AW 2002, 'Crystal structure of biphalin sulfate: A multireceptor opioid peptide', Journal of Peptide Research, vol. 59, no. 3, pp. 123-133. https://doi.org/10.1046/j.1397-002x.2001.10967.x
Flippen-Anderson, J. L. ; Deschamps, J. R. ; George, C. ; Hruby, Victor J ; Misicka, A. ; Lipkowski, A. W. / Crystal structure of biphalin sulfate : A multireceptor opioid peptide. In: Journal of Peptide Research. 2002 ; Vol. 59, No. 3. pp. 123-133.
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