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Dermorphin

Dermorphin is a hepta-peptide first isolated from the skin of South American frogs belonging to the family Phyllomedusinae.^[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]

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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

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. 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. PMID 8633012.