58822-25-6

Basic information

• Product Name: [LEU5]-ENKEPHALIN
• Synonyms: L-TYR-GLY-GLY-PHE-LEU;LEUCINE-ENKEPHALIN (HUMAN, PORCINE, BOVINE, RAT, MOUSE);LEUCINE-ENKEPHALIN (HUMAN, PORCINE, BOVINE, RAT, MOUSE) H2O;LEUCINE-ENKEPHALIN;LEU-ENKEPHALIN;[LEU5]-ENKEPHALIN;ENKEPHALIN, LEU5-, HUMAN;ENKEPHALIN L
• CAS NO: 58822-25-6
• Molecular Formula: C₂₈H₃₇N₅O₇
• Molecular Weight: 555.62
• EINECS: 261-457-1
• Product Categories: Peptide;Opioid receptor and opioid-like receptor;Pepetides;peptides
• Mol File: 58822-25-6.mol
• Article Data: 63

Chemical Properties

• Melting Point: 130-133 °C
• Boiling Point: 998.8 °C at 760 mmHg
• Flash Point: 557.8 °C
• Appearance: White lyophilized powder
• Density: 1.274 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.586
• Storage Temp.: −20°C
• Solubility: ≥54.6 mg/mL in H2O; ≥54.8 mg/mL in EtOH; ≥55.6 mg/mL in DMSO
• PKA: 3.40±0.10(Predicted)
• Water Solubility: Soluble in water (1 mg/ml ).
• CAS DataBase Reference: [LEU5]-ENKEPHALIN(CAS DataBase Reference)
• NIST Chemistry Reference: [LEU5]-ENKEPHALIN(58822-25-6)
• EPA Substance Registry System: [LEU5]-ENKEPHALIN(58822-25-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 58822-25-6(Hazardous Substances Data)

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.

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

Upstream product

• 2130-96-3 O-benzyl-N-tert-butoxycarbonyl-L-tyrosine 
• 85541-31-7 Glycyl-glycyl-(S)-phenylalanyl-(S)-leucinmethylesterhydrochlorid 
• 64963-27-5 N-tert-butyloxycarbonyl-L-tyrosyl-glycyl-glycyl-L-phenylalanyl-L-leucine 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 47375-34-8 Boc-Tyr(t-Bu)-OH 
• 28635-78-1 L-phenylalanyl-L-leucine tert-butyl ester 
• 69729-16-4 N-benzyloxycarbonyl-L-tyrosyl-glycyl-glycyl-L-phenylalanyl-L-leucine benzyl ester 
• 74974-13-3 benzyl ester of N-benzyloxycarbonyl-O-benzyltyrosylglycylglycylphenylalanylleucine 
• 134532-08-4 BocTyr(2-BrZ)GlyGlyPheLeuOH 
• 77427-00-0 Boc-Tyr-Gly-Gly-Phe-Leu-OBu^t 
• 122269-93-6 DC-FM-bar-Tyr(t-Bu)-Gly-Gly-Phe-Leu-O-t-Bu 
• 107940-59-0 Trt-Tyr-Gly-Gly-Phe-Leu-ODpm 
• 119866-73-8 Boc-Tyr-Gly-Gly-Phe-Leu-OCet 
• 92176-57-3 Trt-Tyr-Gly-Gly-Phe-Leu-OtBu 

Downstream Products

• 80507-99-9 Q-Tyr-Gly-Gly-Phe-Leu-OH 
• 149207-52-3 FMOC-L-Tyr-Gly-Gly-L-Phe-L-Leu-OH 
• 98317-57-8 Tert-butyloxycarbonylmethionyl-tyrosyl-glycyl-glycyl-phenylalanyl-leucine 
• 78922-82-4 acetyl leucine enkephalin 
• 129785-74-6 (S)-2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-{[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryloxy}-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid 
• 61-90-5 L-leucine 
• 60254-82-2 L-tyrosylglycylglycyl-L-phenylanine 
• 328-39-2 LEUCINE 
• 98317-54-5 Methionyl-tyrosyl-glycyl-glycyl-phenylalanyl-leucine 
• 129785-81-5 phospho-Tyr-Gly-Gly-Phe-Leu-OH 
• 81704-75-8 NH₃CHCH₂C₆H₄OHCONHCH₂CONHCH₂CONHCHCH₂C₆H₅CONHCHCOOCH₂CH₂SCH₃Co(NH₃)5⁽³⁺⁾*3CF₃COO^(1-) 
• 81688-63-3 NH₃CHCH₂C₆H₄OHCONHCH₂CONHCH₂CONHCHCH₂C₆H₅CONHCHCOOCH₂CH(CH₃)2Co(NH₃)5⁽³⁺⁾*3CF₃COO^(1-) 
• 60254-84-4 H-3,5-diiodo-Tyr-Gly-Gly-Phe-Leu-OH 
• 95231-17-7 C₂₈H₃₆N₆O₉ 

Relevant articles and documents

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

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

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

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

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.

METHOD FOR PREPARING PEPTIDES

The invention relates to a method for preparing peptides comprising the step of forming a peptide bond wherein the carboxyl group of a first amino acid or first peptide is activated and an amino group of the first activated amino acid or first peptide is protected by a protecting group having a water-solubility enhancing group and the activated carboxyl group of the first amino acid or first peptide is reacted with an amino group of a second amino acid or second peptide wherein said carboxyl group of the first amino acid or first peptide is activated in the absence of the second amino acid or second peptide. The invention further relates to peptides comprising a protecting group having a water-solubility enhancing group being bound to the amino group and an activated or free carboxyl group.