 | |
| Names | |
|---|---|
| IUPAC names (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-4-(methylsulfanyl)butanamido]-3-phenylpropanamido]-3-(1H-imidazol-4-yl)propanamido]-4-methylpentanamido]-4-(methylsulfanyl)butanamido]-3-carbamoylpropanoic acid or L-tyrosyl-D-methionyl-L-phenylalanyl-L-histidyl-L-leucyl-L-methionyl-L-α-asparagine | |
| Other names Deltorphin A; Dermenkephalin | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
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| Properties | |
| C44H62N10O10S2 | |
| Molar mass | 955.154 g/mol |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Deltorphin, also known asdeltorphin A anddermenkephalin, is anaturally occurring,exogenousopioidheptapeptide and thus,exorphin, with theamino acid sequence Tyr-D-Met-Phe-His-Leu-Met-Asp-NH2.[1][2][3] Along with the other deltorphins (such asdeltorphin I anddeltorphin II) and thedermorphins, deltorphin isendogenous tofrogs of the genusPhyllomedusa such asP. bicolor andP. sauvagei where it is produced in their skin, and is not known to occur naturally in any other species.[1][2][4] Deltorphin is one of the highestaffinity and mostselective naturally occurring opioid peptides known, acting as a verypotent and highly specificagonist of theδ-opioid receptor.[1][2][3]
Deltorphins have an unusually high blood–brain barrier penetration rate. The nonselective opiate antagonistnaloxone inhibits deltorphin uptake by brain microvessels, but neither the selective δ-opioid antagonistnaltrindole nor a number of opioid peptides with different affinities for δ- or μ-opioid receptors compete with deltorphins for the transport.[5]
