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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

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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Pattern of distribution of neuropeptides in the camel lacrimal gland.
Adeghate E
Neuropeptides, 30(6), 566-571 (1996)
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
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
F Bolacchi et al.
Neurochemical research, 21(8), 875-884 (1996-08-01)
The hydrolysis of leucine enkephalin by the proteolytic enzymes present in human and rabbit plasma has been studied by kinetic and chromatographic techniques. Data obtained indicate the existence of noticeable intraspecific differences in the kinetics of leu-enkephalin degradation, and of
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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