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Mu-opioid receptor agonists
DADLE
Другие языки:

DADLE

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DADLE
2-D-Alanine-5-D-leucine-enkephalin.png
Names
IUPAC name
(2R)-2-[[(2S)-2-[[2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid
Other names
• [D-Ala2, D-Leu5]-Enkephalin
• L-Tyrosyl-D-alanylglycyl-L-phenylalanyl-D-Leucine
• N-(N-(N-(N-L-tyrosyl-D-alanyl)glycyl)-L-phenylalanyl)-D-Leucine
• Tyr-D-Ala-Gly-Phe-D-Leu-OH
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.059.337
PubChem CID
UNII
  • InChI=1S/C29H39N5O7/c1-17(2)13-24(29(40)41)34-28(39)23(15-19-7-5-4-6-8-19)33-25(36)16-31-26(37)18(3)32-27(38)22(30)14-20-9-11-21(35)12-10-20/h4-12,17-18,22-24,35H,13-16,30H2,1-3H3,(H,31,37)(H,32,38)(H,33,36)(H,34,39)(H,40,41)/t18-,22+,23+,24-/m1/s1 ☒N
    Key: ZHUJMSMQIPIPTF-IBURTVSXSA-N ☒N
  • InChI=1/C29H39N5O7/c1-17(2)13-24(29(40)41)34-28(39)23(15-19-7-5-4-6-8-19)33-25(36)16-31-26(37)18(3)32-27(38)22(30)14-20-9-11-21(35)12-10-20/h4-12,17-18,22-24,35H,13-16,30H2,1-3H3,(H,31,37)(H,32,38)(H,33,36)(H,34,39)(H,40,41)/t18-,22+,23+,24-/m1/s1
    Key: ZHUJMSMQIPIPTF-IBURTVSXBS
  • N[C@H](C(N[C@H](C)C(NCC(N[C@@H](CC1=CC=CC=C1)C(N[C@H](CC(C)C)C(O)=O)=O)=O)=O)=O)CC2=CC=C(O)C=C2
Properties
C29H39N5O7
Molar mass 569.659 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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DADLE ([D-Ala2, D-Leu5]-Enkephalin) is a synthetic opioid peptide with analgesic properties. Although it is often considered a selective delta opioid receptor agonist, it also binds to the μ1 subtype of mu opioid receptors.

Treatment with DADLE results in transient depression of mean arterial blood pressure and heart rate.

Its peptide sequence is Tyr-D-Ala-Gly-Phe-D-Leu.

See also




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