Synthesis and biological activity of some glucose‐enkephalin conjugates
- 1 September 1987
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 30 (3), 371-378
- https://doi.org/10.1111/j.1399-3011.1987.tb03344.x
Abstract
Two O-glucopeptides, H-Ty(.beta.-D-Glc)-Gly-Gly-Phe-OH(10) and H-Tyr(.beta.-D-Glc)-Gly-Gly-Phe-Leu-OH (11), having the amino acid sequence of enkephalin, were synthesized to determine the influence of the carbohydrate molecule on the biological activity and conformation of these opioid peptides. The synthesis were carried out in a stepwise and/or direct manner by fusing the activated O-glucosylpseudourea intermediate with suitably protected amino acid or peptide derivatives, followed by hydrogenolytic removal of protecting groups. The pure compounds were tested for opiate-like activity by using the guinea pig ileum (GPI) and mouse was deferens (MVD) preparations.Keywords
This publication has 16 references indexed in Scilit:
- A New Utility ofO-Glycosylpseudoureas for Synthesis of Glucopeptides and (1 → 6)-DisaccharidesSynthesis, 1986
- A novel glycosyl-amino acid linkage: Rabbit-muscle glycogen is covalently linked to a protein via tyrosineBiochemical and Biophysical Research Communications, 1985
- Conformational study of glycopeptidesInternational Journal of Peptide and Protein Research, 1984
- Glycoproteins: their structure, biosynthesis and possible clinical implicationsClinical Biochemistry, 1984
- Studies on amino acids and peptides. Part 6. Methods for introducing thioamide bonds into the peptide backbone: synthesis of the four monothio analogues of leucine enkephalinJournal of the Chemical Society, Perkin Transactions 1, 1984
- A Rapid Leu‐Enkephaline Synthesis in SolutionJournal für Praktische Chemie, 1984
- Synthesis and pharmacological characterization in vitro of cyclic enkephalin analogs: effect of conformational constraints on opiate receptor selectivityJournal of Medicinal Chemistry, 1982
- Opioid activities of fragments of β-endorphin and of ites leucine65-analogue. Comparison of the binding properties of methionine- and leucine-enkephalinEuropean Journal of Pharmacology, 1979
- Solution conformation of enkephalin. A nuclear magnetic resonance study of 13C-enriched carbonyl carbons in [Leu5]-enkephalinBiochemistry, 1979
- Unsulfated C-terminal 7-peptide of cholecystokinin: A new ligand of the opiate receptorBiochemical and Biophysical Research Communications, 1978