Leucine enkephalin

Base Information

• Chemical Name: Leucine enkephalin
• CAS No.: 58822-25-6
• Molecular Formula: C28H37 N5 O7
• Molecular Weight: 569.658
• NSC Number: 350588
• Wikidata: Q27080195
• Mol file: 58822-25-6.mol

Synonyms:5 Leucine Enkephalin;5-Leucine Enkephalin;Enkephalin, 5-Leucine;Enkephalin, Leucine;Leu Enkephalin;Leu(5)-Enkephalin;Leu-Enkephalin;Leucine Enkephalin

Chemical Property of Leucine enkephalin

Chemical Property:

• Appearance/Colour: White lyophilized powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 130-133 °C
• Boiling Point: 998.8 °C at 760 mmHg
• PKA: 3.40±0.10(Predicted)
• Flash Point: 557.8 °C
• PSA: 199.95000
• Density: 1.274 g/cm³
• LogP: 2.10130
• Storage Temp.: −20°C
• Solubility.: ≥54.6 mg/mL in H2O; ≥54.8 mg/mL in EtOH; ≥55.6 mg/mL in DMSO
• Water Solubility.: Soluble in water (1 mg/ml ).
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 15
• Exact Mass: 555.26929854
• Heavy Atom Count: 40
• Complexity: 854

Purity/Quality:

99% ^*data from raw suppliers

[Leu5]-Enkephalin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CC(C(=O)O)NC(=O)C(CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)C(CC2=CC=C(C=C2)O)N
• Uses: Endogenous opioid neurotransmitter/neuromodulator that is an agonist at ? and δ opioid receptors, localization in brain parallels the localization of δ receptors.

Technology Process of Leucine enkephalin

There total 153 articles about Leucine enkephalin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

benzyl ester of N-benzyloxycarbonyl-O-benzyltyrosylglycylglycylphenylalanylleucine (74974-13-3) → Leu-enkephalin (58822-25-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; for 6h;

DOI:10.1007/BF00597660

Reference yield: 95.0%

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) + N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + N-Fmoc L-Phe (35661-40-6) + Fmoc-Tyr(tBu)-OH (71989-38-3,118488-18-9,204384-67-8) → Leu-enkephalin (58822-25-6)

Guidance literature:

N-tert-butoxycarbonyl-L-leucine; at 50 ℃; Ionic liquid; Inert atmosphere;

With water; sodium hydroxide; In tetrahydrofuran;

N-(fluoren-9-ylmethoxycarbonyl)glycine; N-Fmoc L-Phe; Fmoc-Tyr(tBu)-OH; Temperature; Further stages;

Reference yield: 94.3%

methyl (L)-leucinate hydrochloride (7517-19-3) + methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) + L-tyrosine methyl ester HCl (3417-91-2) + methoxycarbonylmethylamine (616-34-2) → Leu-enkephalin (58822-25-6)

Guidance literature:

L-tyrosine methyl ester HCl; at 50 ℃; Ionic liquid; Inert atmosphere;

With trifluoroacetic acid;

methyl (L)-leucinate hydrochloride; methyl (2S)-2-amino-3-phenylpropanoate hydrochloride; methoxycarbonylmethylamine; Temperature; Further stages;

upstream raw materials:

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

Glycyl-glycyl-(S)-phenylalanyl-(S)-leucinmethylesterhydrochlorid

N-tert-butyloxycarbonyl-L-tyrosyl-glycyl-glycyl-L-phenylalanyl-L-leucine

glycine ethyl ester hydrochloride

Downstream raw materials:

Q-Tyr-Gly-Gly-Phe-Leu-OH

FMOC-L-Tyr-Gly-Gly-L-Phe-L-Leu-OH

Tert-butyloxycarbonylmethionyl-tyrosyl-glycyl-glycyl-phenylalanyl-leucine

acetyl leucine enkephalin

Refernces

Solid-phase synthesis of O-linked glycopeptide analogues of enkephalin

10.1021/jo005712m

The study focuses on the solid-phase synthesis of O-Linked Glycopeptide Analogues of Enkephalin, which are peptide opiates designed to investigate the role of glycoside moieties and carbohydrate-peptide linkage regions in blood-brain barrier transport, opiate receptor binding, and analgesia. The researchers synthesized 18 N-R-FMOC-amino acid glycosides using Hanessian's modification of the Koenigs-Knorr reaction, incorporating various monosaccharides and disaccharides into 22 enkephalin glycopeptide analogues. These glycosides served as building blocks for the glycopeptides, which were assembled on Rink resin using FMOC peptide strategy. The study also explored the impact of different protecting groups and aglycone/glycosyl bromide pairs on the glycosylation yields and selectivity, optimizing the synthesis process for the glycopeptides. The chemicals used in the study include various amino acids, glycosyl bromides, protecting agents, and resins, all serving specific roles in the synthesis and protection of the glycopeptides during assembly.

PROTECTION OF THE CARBOXY GROUP IN THE FORM OF THE 2-CYANOETHYL ESTERS IN SYNTHESIS OF PEPTIDES

10.1007/BF00598586

The research investigates the use of the 2-cyanoethyl (Cet) group for protecting carboxylic functions in peptide synthesis. The study synthesizes Cet esters of several tert-butoxycarbonylated (Boc) amino acids and uses Cet protection for the C-terminal carboxy groups in the synthesis of the pentapeptide leucine-enkephalin. The Cet esters are found to be stable under acidic conditions and can be selectively cleaved by strong organic bases under nonhydrolytic conditions, providing a useful alternative to methyl and benzyl esters. The overall yield of leucine-enkephalin synthesis is 38%, and its structure is confirmed by amino acid analysis and mass spectra. The study also shows that Cet esters can be converted into hydrazides for fragment condensation by the azide method.