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L9133

Sigma-Aldrich

Leucine Enkephalin acetate salt hydrate

≥95% (HPLC)

Synonym(s):

Leucine Enkephalin

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About This Item

Empirical Formula (Hill Notation):
C28H37N5O7 · xC2H4O2 · yH2O
Molecular Weight:
555.62 (anhydrous free base basis)
MDL number:
MFCD11045938
UNSPSC Code:
12352209
eCl@ss:
32160409
PubChem Substance ID:
329817669
NACRES:
NA.32

Quality Level

200

Assay

≥95% (HPLC)

storage temp.

−20°C

SMILES string

O.CC(O)=O.CC(C)C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc2ccc(O)cc2)C(O)=O

InChI

1S/C28H37N5O7.C2H4O2.H2O/c1-17(2)12-23(28(39)40)33-27(38)22(14-18-6-4-3-5-7-18)32-25(36)16-30-24(35)15-31-26(37)21(29)13-19-8-10-20(34)11-9-19;1-2(3)4;/h3-11,17,21-23,34H,12-16,29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,33,38)(H,39,40);1H3,(H,3,4);1H2/t21-,22-,23-;;/m0../s1

InChI key

QKDIOZBQOQJXFR-XQCXOTTHSA-N

Gene Information

human ... OPRD1(4985) , OPRM1(4988)
mouse ... OPRD1(18386) , OPRM1(18390)
rat ... OPRD1(24613) , OPRM1(25601)

Amino Acid Sequence

Tyr-Gly-Gly-Phe-Leu

General description

Leucine Enkephalin is a pentapeptide and is a normal component of central and peripheral tissues. Leucine Enkephalin has amino acid sequence Tyr-Gly-Gly-Phe-Leu and is distributed in the brains of many animals, including humans. It is an endogenous opioid neurotransmitter/neuromodulator localized in brain parallels and in δ receptors.

Application

Leucine Enkephalin acetate salt hydrate has been used in the calibration of the Q-Tof Micro hybrid, triple quadrupole-orthogonal acceleration time of flight (TOF) instrument in single-stage TOF mode. It has also been used to perform the calibration of mass spectrometry. It has also been used in liquid chromatography-mass spectrometry (LCMS)/MS for calibration of the system and for relative correction of the spectra.

Biochem/physiol Actions

Leucine Enkephalin (LEU-ENK) functions as agonists at both μ- and δ-opioid receptor sites. It might also play a role as neurotransmitter agent at morphine-sensitive synapses. Leucine Enkephalin is also associated with pain regulation. LEU-ENK expressed in camel lacrimal nerve regulates lacrimal fluid and protein secretion. LEU-ENK is degraded during metabolism by several enzymes, including aminopeptidase-N (APN), neutral endopeptidase (NEP), dipeptidyl peptidase- 3 (DPP3), carboxy peptidase-A6 (CPA-6) and angiotensin converting enzyme (ACE), which are sometimes referred to as enkephalinases.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000399198
0000399198
0000420149
0000420149
0000388527

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J Hughes et al.
Nature, 258(5536), 577-580 (1975-12-18)
Enkephalin, a natural ligand for opiate receptors is composed of the pentapepides H-Tyr-Gly-Gly-Phe-Met-OH and H-Tyr-Gly-Gly-Phe-Leu-OH. The evidence is based on the determination of the amino acid sequence of natural enkephalin by the dansyl-Edman procedure and by mass spectrometry followed by
Pattern of distribution of neuropeptides in the camel lacrimal gland.
Adeghate E
Neuropeptides, 30(6), 566-571 (1996)
An enzyme-linked immunosorbent assay for detecting 3-phenoxybenzoic acid in plasma and its application in farmers and consumers.
Thiphom S
Analytical Methods : Advancing Methods and Applications, 4(11), 3772-3778 (2012)
S R George et al.
The Journal of biological chemistry, 275(34), 26128-26135 (2000-06-08)
The existence of dimers and oligomers for many G protein-coupled receptors has been described by us and others. Since many G protein-coupled receptor subtypes are highly homologous to each other, we examined whether closely related receptors may interact with each
A P Sayani et al.
Journal of pharmaceutical sciences, 82(11), 1179-1185 (1993-11-01)
Leucine enkephalin (Tyr-Gly-Gly-Phe-Leu; Leu-Enk) is a naturally occurring peptide that has been shown to have pain modulating properties. To evaluate the feasibility of using various absorptive mucosae as a route of systemic delivery, the stability of Leu-Enk and the effect
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