[D-Leu2]deltorphin, a 17 amino acid opioid peptide from the skin of the Brazilian hylid frog, Phyllomedusa burmeisteri.
A novel 17 amino acid peptide, having a D-leucine in position 2 of its sequence, has been isolated from methanol extracts of the skin of the Brazilian frog, Phyllomedusa burmeisteri. The sequence of the peptide is: Tyr-D-Leu-Phe-Ala-Asp-Val-Ser-Thr-Ile-Gly-Asp-Phe-Phe-His-Ser-Ile-NH2. It displays a poor affinity for delta-opioid binding sites, both in the periphery and in the central nervous system. However, the shorter synthetic amidated analogue (1-10) possess both on the central and peripheral delta binding sites an agonistic potency equalling in affinity and exceeding in selectivity that of the enkephalins. The shorter amidated analogue (1-7) is virtually inactive on opioid binding sites in the periphery, but displays a clear-cut affinity for both delta and mu binding sites on rat brain membranes. To date six different D-amino acid residues have been found, always in position 2 of the sequence, in as many as 11 natural peptide molecules of animal origin.
Barra
D
D
Dipartimento di Scienze Biochimiche, Università La Sapienza, Roma, Italy.
Mignogna
G
G
Simmaco
M
M
Pucci
P
P
Severini
C
C
Falconieri-Erspamer
G
G
Negri
L
L
Erspamer
V
V
D000595:Amino Acid Sequence; D000818:Animals; D001681:Biological Assay; D001921:Brain / Q000378:metabolism; D001938:Brazil; D006224:Cricetinae; D004723:Endorphins / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D008297:Male; D051379:Mice; D008969:Molecular Sequence Data; D018847:Opioid Peptides; D010455:Peptides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D011898:Ranidae; D051381:Rats; D011957:Receptors, Opioid / Q000378:metabolism; D012867:Skin / Q000737:chemistry*; D013237:Stereoisomerism; D014649:Vas Deferens / Q000187:drug effects
D004723:Endorphins; D018847:Opioid Peptides; D010455:Peptides; D011957:Receptors, Opioid; C087834:deltorphin, Leu(2)-