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E5008

Sigma-Aldrich

[D-Ala2]-Leucine enkephalin

≥97% (HPLC), suitable for ligand binding assays

Synonym(s):

Tyr-D-Ala-Gly-Phe-Leu

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About This Item

Empirical Formula (Hill Notation):
C29H39N5O7
CAS Number:
64963-01-5
Molecular Weight:
569.65
EC Number:
265-291-0
MDL number:
MFCD00076409
UNSPSC Code:
12352209
PubChem Substance ID:
24894597
NACRES:
NA.26

product name

[D-Ala2]-Leucine enkephalin, ≥97% (HPLC)

Quality Level

200

assay

≥97% (HPLC)

form

powder

technique(s)

ligand binding assay: suitable

color

white

storage temp.

−20°C

SMILES string

CC(C)CC(NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)C(C)NC(=O)C(N)Cc2ccc(O)cc2)C(O)=O

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)

InChI key

ZHUJMSMQIPIPTF-UHFFFAOYSA-N

Related Categories

Amino Acid Sequence

Tyr-Ala-Gly-Phe-Leu

Biochem/physiol Actions

The Enkephalin amid peptide [D-Ala2]-Leucine enkephalin ((DADLE), a delta opioid agonist, is a degradation resistant long-acting Leu-enkephalin analog used to study the signaling pathway of delta opioid receptors.

Other Notes

Potent, long-acting Leu-enkephalin analog that is resistant to enzymatic degradation

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Arndt Psurek et al.
Electrophoresis, 27(5-6), 1199-1208 (2006-03-09)
Nonaqueous capillary electrophoresis with electrochemical detection (NACE-ED) was applied to the analysis of enkephalin peptides. The effect of different buffer compositions on the electrophoretic behavior of methionine enkephalin, leucine enkephalin, and [D-Ala2]-leucine enkephalin was studied. Separation of the protonated and
A M Ostermeier et al.
Anesthesiology, 93(4), 1053-1063 (2000-10-06)
The mechanism underlying the depressant effect of opioids on neuronal activity within the neocortex is still not clear. Three modes of action have been suggested: (1) inhibition by activation of postsynaptic potassium channels, (2) interaction with postsynaptic glutamate receptors, and
A R Burt et al.
The Biochemical journal, 320 ( Pt 1), 227-235 (1996-11-15)
Rat-1 fibroblasts were transfected with a cDNA encoding the mouse delta opioid receptor. Two separate clones, D2 (which expressed some 6 pmol of the receptor/mg of membrane protein) and DOE (which expressed some 0.2 pmol/mg of membrane protein), were examined
Y Lin et al.
European journal of pharmacology, 262(1-2), 99-106 (1994-09-01)
Opiates increase firing of rat medial vestibular nucleus neurons. We have attempted to determine the mechanism of these excitatory opiate actions by extracellular recording of neuronal activity with ionophoretic application of opiate agonists and bath application of antagonists. The spontaneous
S E Thompson et al.
Journal of cardiovascular pharmacology, 24(5), 818-825 (1994-11-01)
Leucine enkephalin (YGGFL) effects on markers for transcellular and paracellular permeation across the blood-brain barrier (BBB) were investigated in vitro with bovine brain microvessel endothelial cell (BMEC) monolayers in primary culture. Intact YGGFL, but not metabolites of YGGFL, stimulated BMEC

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