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58822-25-6

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58822-25-6 Usage

Description

[LEU5]-ENKEPHALIN is a naturally occurring pentapeptide that functions as an endogenous opioid neurotransmitter and neuromodulator. It acts as an agonist at both μ (mu) and δ (delta) opioid receptors, playing a significant role in the modulation of pain perception, stress response, and reward systems in the brain. The localization of [LEU5]-ENKEPHALIN in the brain closely mirrors the distribution of δ receptors, indicating its importance in various physiological processes.

Uses

Used in Pharmaceutical Industry:
[LEU5]-ENKEPHALIN is used as an analgesic agent for its ability to alleviate pain by binding to μ and δ opioid receptors in the central nervous system. This interaction leads to the inhibition of neurotransmitter release, resulting in reduced pain perception.
Used in Neurological Research:
As a neurotransmitter and neuromodulator, [LEU5]-ENKEPHALIN is used in the study of various neurological disorders and conditions related to pain, stress, and addiction. Understanding its role in these processes can help researchers develop targeted therapies and interventions for improved patient outcomes.
Used in Drug Development:
The agonistic properties of [LEU5]-ENKEPHALIN at μ and δ opioid receptors make it a valuable compound in the development of new drugs for pain management, stress relief, and addiction treatment. Its unique interaction with these receptors can be leveraged to create more effective and safer medications with fewer side effects.
Used in Neuroimaging Studies:
[LEU5]-ENKEPHALIN can be utilized as a molecular probe in neuroimaging studies to visualize the distribution and density of μ and δ opioid receptors in the brain. This information can be crucial for understanding the underlying mechanisms of various neurological conditions and for developing targeted therapies.

Check Digit Verification of cas no

The CAS Registry Mumber 58822-25-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,8,8,2 and 2 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 58822-25:
(7*5)+(6*8)+(5*8)+(4*2)+(3*2)+(2*2)+(1*5)=146
146 % 10 = 6
So 58822-25-6 is a valid CAS Registry Number.
InChI:InChI=1/C28H37N5O7/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/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)/t21-,22-,23-/m0/s1

58822-25-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name [LEU5]-ENKEPHALIN

1.2 Other means of identification

Product number -
Other names ENKEPHALIN L

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:58822-25-6 SDS

58822-25-6Relevant articles and documents

Cobalt(III)-Mediated Peptide Synthesis. 2. Synthesis of Tetrapeptides and 5>enkephalin

Knighton, D. R.,Harding, D. R. K.,Friar, M. J.,Hancock, W. S.,Reynolds, G. D.,et al.

, p. 7025 - 7026 (1981)

-

The pivaloylglycol anchor group: A new platform for a photolabile linker in solid-phase synthesis

Peukert, Stefan,Giese, Bernd

, p. 9045 - 9051 (1998)

We have designed a new photolabile linker (2) based on 2- pivaloylglycerol for the solid-phase synthesis of acids. The linker was prepared in six steps and anchored to the support via an amide bond. Photocleavage is a two-step process, in which the immobilized acids are released by photolyric generation of a radical center and subsequent spontaneous β-C,O bond scission. The pivaloyl linker (2) was found to cleave with high yields and purities the acids in various solvents (THF, CH2Cl2, dioxane, DMSO) by irradiation with light above 320 nm. Using this linker, we have demonstrated the solid-phase synthesis of test compounds by peptide synthesis, palladium-catalyzed cross coupling, and epoxidation. The linker proved to be stable toward the treatment with acids and bases. The photolysis rates of our pivaloyl linker (2) were compared with the rates of a o- nitrobenzyl photolinker (1) and proved to be superior.

Peptide synthesis on fluorous support

Mizuno, Mamoru,Goto, Kohtaro,Miura, Tsuyoshi,Matsuura, Takeshi,Inazu, Toshiyuki

, p. 3425 - 3428 (2004)

New fluorous supports were synthesized and used to prepare a peptide having a C-terminal COOH based on fluorous chemistry. The hexakisfluorous chain-type support was suitable for the synthesis of a pentapeptide or a peptide derivative on a fluorous support whose fluorine content is over 40 w/w%. A bioactive peptide, Leu-enkephalin, was easily synthesized using an Fmoc-strategy based on fluorous chemistry.

Sustainable Peptide Synthesis Enabled by a Transient Protecting Group

Avrutina, Olga,Knauer, Sascha,Koch, Niklas,Kolmar, Harald,Meusinger, Reinhard,Uth, Christina

supporting information, p. 12984 - 12990 (2020/06/01)

The growing interest in synthetic peptides has prompted the development of viable methods for their sustainable production. Currently, large amounts of toxic solvents are required for peptide assembly from protected building blocks, and switching to water as a reaction medium remains a major hurdle in peptide chemistry. We report an aqueous solid-phase peptide synthesis strategy that is based on a water-compatible 2,7-disulfo-9-fluorenylmethoxycarbonyl (Smoc) protecting group. This approach enables peptide assembly under aqueous conditions, real-time monitoring of building block coupling, and efficient postsynthetic purification. The procedure for the synthesis of all natural and several non-natural Smoc-protected amino acids is described, as well as the assembly of 22 peptide sequences and the fundamental issues of SPPS, including the protecting group strategy, coupling and cleavage efficiency, stability under aqueous conditions, and crucial side reactions.

N-Guanidyl and C-Tetrazole Leu-Enkephalin Derivatives: Efficient Mu and Delta Opioid Receptor Agonists with Improved Pharmacological Properties

Beaudeau, Jean-Louis,Blais, Véronique,Holleran, Brian J.,Bergeron, Alexandre,Pineyro, Graciela,Guérin, Brigitte,Gendron, Louis,Dory, Yves L.

, p. 1615 - 1626 (2019/02/01)

Leu-enkephalin and d-Ala2-Leu-enkephalin were modified at their N- and C-termini with guanidyl and tetrazole groups. The resulting molecules were prepared in solution or by solid phase peptide synthesis. The affinity of the different analogues at mu (MOP) and delta opioid receptors (DOP) was then assessed by competitive binding in stably transfected DOP and MOP HEK293 cells. Inhibition of cAMP production and recruitment of β-arrestin were also investigated. Finally, lipophilicity (logD7.4) and plasma stability of each compound were measured. Compared to the native ligands, we found that the replacement of the terminal carboxylate by a tetrazole slightly decreased both the affinity at mu and delta opioid receptors as well as the half-life. By contrast, replacing the ammonium at the N-terminus with a guanidyl significantly improved the affinity, the potency, as well as the lipophilicity and the stability of the resulting peptides. Replacing the glycine residue with a d-alanine in position 2 consistently improved the potency as well as the stability of the analogues. The best peptidomimetic of the whole series, guanidyl-Tyr-d-Ala-Gly-Phe-Leu-tetrazole, displayed sub-nanomolar affinity and an increased lipophilicity. Moreover, it proved to be stable in plasma for up to 24 h, suggesting that the modifications are protecting the compound against protease degradation.

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