60284-47-1

Basic information

• Product Name: [ALA2 , LEU5 ]-ENKEPHALIN
• Synonyms: (ala2)-leucine enkephalin;(alanine2)leucine enkephalin
• CAS NO: 60284-47-1
• Molecular Formula: C₂₉H₃₉N₅O₇
• Molecular Weight: 569.655
• Mol File: 60284-47-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: ?20°C
• CAS DataBase Reference: [ALA2 , LEU5 ]-ENKEPHALIN(CAS DataBase Reference)
• NIST Chemistry Reference: [ALA2 , LEU5 ]-ENKEPHALIN(60284-47-1)
• EPA Substance Registry System: [ALA2 , LEU5 ]-ENKEPHALIN(60284-47-1)

Safety Data

• Hazardous Substances Data: 60284-47-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
[ALA2, LEU5]-ENKEPHALIN is used as a therapeutic agent for its pain-relieving properties. It is particularly useful in the management of various types of pain due to its potent analgesic effects.
Used in Neuroscience Research:
[ALA2, LEU5]-ENKEPHALIN is used as a research tool to study the central nervous system and its role in pain relief and mood regulation. [ALA2 , LEU5 ]-ENKEPHALIN can provide valuable insights into the mechanisms of pain and mood disorders, potentially leading to the development of new treatments for these conditions.
Used in Drug Development:
[ALA2, LEU5]-ENKEPHALIN is used as a starting point for the development of new drugs targeting pain management and mood disorders. Its potent analgesic properties and ability to modulate mood make it a promising candidate for the creation of novel pharmaceuticals.

Upstream product

• 108607-68-7 H-L-Tyr(Dmp)-D-Ala-Gly-L-Phe-D-Leu-OH 
• 19391-35-6 N-tert-butoxycarbonyl-L-tyrosine benzyl ester 
• 28635-78-1 L-phenylalanyl-L-leucine tert-butyl ester 
• 108607-61-0 Boc-L-Tyr(Dmp)-OBzl 
• 108607-66-5 Boc-L-Tyr(Dmp)-D-Ala-Gly-OH 
• 108607-67-6 Boc-L-Tyr(Dmp)-D-Ala-Gly-L-Phe-D-Leu-OBu(t) 
• 131124-60-2 2,4,5-didehydro-L-Leu⁵>Leu-enkephalin 
• 73965-71-6 N^α-(tert-butoxycarbonyl)-2,Leu⁵>enkephalin 
• 131177-58-7 Fmoc-4,5-didehydro-DL-leucine 
• 127633-32-3 Fmoc-4,5-didehydro-D,L-leucine Benzotriazole Ester 
• 139143-41-2 {(S)-2-(4-Benzyloxy-phenyl)-1-[(R)-1-(hydrazinocarbonylmethyl-carbamoyl)-ethylcarbamoyl]-ethyl}-carbamic acid benzyl ester 
• 139143-40-1 {(R)-2-[(S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-propionylamino]-propionylamino}-acetic acid methyl ester 
• 86827-18-1 N-benzyloxycarbonyl-O-benzyl-L-tyrosine 

Relevant articles and documents

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.

Synthesis and antinociceptive activity of [D-Ala2]Leu-enkephalin derivatives conjugated with the adamantane moiety

Based on the physicochemical and pharmacological properties of drugs having an adamantane skeleton, an adamantane-based moiety was evaluated as a drug carrier for poorly absorbed compounds, including peptides, active towards the central nervous system (CNS). Seven [D-Ala2]Leu-enkephalin derivatives conjugated with an adamantane-based moiety at the C-terminus or N-terminus were prepared by the solution-phase method and their biological activities were examined. The compounds derivatized at the C-terminus through an ester or amide linkage were much more lipophilic than the parent peptide and exhibited moderate in vitro opioid activity (guinea-pig ileum assay). Among them, four derivatives (1, 2, 4, 5), exhibited significant antinociceptive effects in an in vivo assay (mouse tail-pressure test) after subcutaneous administration. This result suggests that the introduction of the lipophilic adamantane moiety into [D-Ala2]Leu- enkephalin would improve the permeation of the poorly absorbed parent peptide through the blood-brain-barrier (BBB) without loss of antinociceptive effect.

Synthesis of 2>Leu-enkephalin and 2,D-Leu5>Leu-enkephalin with High Specific Tritiated Activity in the Leucine Residue

2>Leu-enkephalin and 2,D-Leu5>Leu-enkephalin (DADLE) labelled with tritium in the leucine residue have been prepared.Synthesis of the precursor peptides, 2,4,5-didehydro-L-Leu5>Leu-enkephalin and 2,4,5-didehydro-D-Leu5>Leu-enkephalin, was carried out by solid-phase synthesis using Fmoc amino acid derivatives, followed by diastereoisomeric separation on HPLC.These peptides were tritiated catalytically to yield DALE with a specific activity of 5.35 TBq mmol-1 and DADLE with that of 5.43 TBq mmol-1, respectively.The distribution of tritium label was investigated by HPLC with a radioisotopic detector following acidic hydrolysis, which confirmed that the tritium label in both labelled peptides was exclusively located at the leucine residue.

METHYLPHOSPHINYL (Dmp): A NEW PROTECTING GROUP OF TYROSINE SUITABLE FOR PEPTIDE SYNTHESIS BY USE OF BOC-AMINO ACIDS

Use of dimethylphosphinyl (Dmp) group as a side-chain phenolic OH protecting group of tyrosine in peptide synthesis was studied.The Dmp group is resistant to trifluoroacetic acid and hydrogenolysis and removed by fluoride ion or liquid HF.

A photoaffinity reagent to label the opiate receptors of guinea pig ileum and mouse vas deferens

An enkephalin derivative, [D-Ala2,Leu5]enkephalin N-[(2-nitro-4-azidophenyl)amino]ethylamide, has been synthesized as a photoaffinity label for the opiate receptor. This compound retains the full biological activity of [D-Ala2,Leu5]enkephalin in guinea pig ileum and mouse vas deferens tests with IC50 values of 4.4 and 2.6 nM, respectively, and inhibits the binding of [3H]naloxone to rat brain membrane preparation with an IC50 value of 2.5 nM. Photolysis of a muscle strip of the guinea pig ileum or of the mouse vas deferens in the presence of the peptide derivative caused irreversible inhibition of electrically stimulated contractions with high efficiencies (80 and 66%, respectively), while the inhibitory effect in the dark was fully reversed by washing. This irreversible inhibition during photolysis was completely prevented by the presence of [D-Ala2,Leu5]enkephalin. These results demonstrate that {D-Ala2,Leu5]-enkephalin N-[(2-nitro-4-azidophenyl)amino]ethylamide is a prominent candidate as a photoaffinity label for the opiate receptor.

Phosphinyl- and Phosphinothioylamino Acids and Peptides. VI. The Protection of the Hydroxyl Function in the Tyrosine Side-chain by the Dimethylphosphinothioyl Group

The use of the dimethylphosphinothioyl (Mpt) group for the protection of the hydroxyl function in the tyrosine side-chain was studied. N,O-Bis(Mpt)tyrosine was obtained directly by a Schotten-Baumann-type reaction of Mpt-Cl with tyrosine. The O-Mpt group was stable under acidic conditions, and it could be removed easily by alkaline hydrolysis or ester-exchange reaction. The usefulness of this new protecting group for the peptide synthesis was shown in the solid-phase synthesis of 2,L-Leu5>-enkephalin(H-L-Tyr-D-Ala-Gly-L-Phe-L-Leu-OH) and its N-allyl derivative.