β‐ENDORPHIN: SYNTHESIS AND ANALGESIC ACTIVITY OF SEVERAL ANALOGS MODIFIED IN POSITIONS 2 AND 5

Donald Yamashiro, Choh Hao Li, Liang‐Fu ‐F Tseng, Horace H. Loh

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

The solid‐phase syntheses of [Sar2]‐, [Ala2]‐, [D‐Leu2]‐, [D‐Lys2]‐β‐ endorphins and [Pro5]‐, [Leu5]‐, [D‐Leu5]‐, [D‐Ala2, D‐Leu5]‐β‐endorphins are described. The synthetic peptides were purified by chromatography on carboxymethylcellulose and partition chromatography on Sephadex G‐50. They were characterized by partition chromatography on agarose, thin‐layer chromatography, paper electrophoresis, and amino acid analyses of acid and enzymic hydrolysates. Bioassay of the synthetic analogs for analgesic activity by the tail‐flick method showed the D‐Leu2 analog to be 48% as potent as βh‐endorphin while the Ala2, D‐Lys2, Leu5, and [D‐Ala2, D‐Leu5] analogs were 8 to 17% as active. The Sar2, D‐Leu5, and Pro5 analogs were less than 1% as potent.

Original languageEnglish (US)
Pages (from-to)251-257
Number of pages7
JournalInternational Journal of Peptide and Protein Research
Volume11
Issue number4
DOIs
StatePublished - Apr 1978

Keywords

  • analgesic activity
  • opioid peptides
  • solid‐phase peptide synthesis
  • β‐endorphin analogs

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