Dermorphin
From Wikipedia, the free encyclopedia
Dermorphin is a hepta-peptide first isolated from the skin of South American frogs belonging to the family Phyllomedusa.[1] The peptide is a natural opiate that binds as an agonist with high potency and selectivity to mu Opioid receptors.[2][3] Dermorphin is about 30-40 times more potent than morphine but less likely to produce drug tolerance and addiction.[4]
Dermorphin is not found in humans or other mammals and similar D-amino acid peptides have only been found in bacteria, amphibians and molluscs.[5] Dermorphin appears to be made in these through an unusual posttranslational modification carried out by an amino acid isomerase.[6] The reason for this unusual process is that the D-alanine in this peptide is not among the 20 in the genetic code and cannot be encoded by the genes by higher organisms.
- Structure of dermorphin: H-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH2
- Chemical formula: C40H50N8O10
- Molecular weight: 802.9 g/mol
[edit] References
- ^ Melchiorri P, Negri L (1996). "The dermorphin peptide family". Gen. Pharmacol. 27 (7): 1099–107. PMID 8981054.
- ^ Amiche M, Delfour A, Nicolas P (1998). "Opioid peptides from frog skin". EXS 85: 57–71. PMID 9949868.
- ^ Erspamer V, Melchiorri P, Falconieri-Erspamer G, et al (1989). "Deltorphins: a family of naturally occurring peptides with high affinity and selectivity for delta opioid binding sites". Proc. Natl. Acad. Sci. U.S.A. 86 (13): 5188–92. doi:. PMID 2544892.
- ^ Broccardo M, Erspamer V, Falconieri Erspamer G, et al (1981). "Pharmacological data on dermorphins, a new class of potent opioid peptides from amphibian skin". Br. J. Pharmacol. 73 (3): 625–31. PMID 7195758.
- ^ Kreil G (1994). "Peptides containing a D-amino acid from frogs and molluscs". J. Biol. Chem. 269 (15): 10967–70. PMID 8157620.
- ^ Heck SD, Faraci WS, Kelbaugh PR, Saccomano NA, Thadeio PF, Volkmann RA (1996). "Posttranslational amino acid epimerization: enzyme-catalyzed isomerization of amino acid residues in peptide chains". Proc. Natl. Acad. Sci. U.S.A. 93 (9): 4036–9. doi:. PMID 8633012.
