[D-Ala2]leucine-enkephalin

Base Information

• Chemical Name: [D-Ala2]leucine-enkephalin
• CAS No.: 64963-01-5
• Molecular Formula: C₂₉H₃₉N₅O₇
• Molecular Weight: 569.658
• European Community (EC) Number: 265-291-0
• UNII: PO4D55T1IG
• Nikkaji Number: J286.615C
• Wikipedia: DADLE
• ChEMBL ID: CHEMBL4539258
• Mol file: 64963-01-5.mol

Synonyms:64963-01-5;[D-Ala2]leucine-enkephalin;Leuphasyl;Tyr-D-Ala-Gly-Phe-Leu;(D-Ala2)leucine-enkephalin;DALLE;H-Tyr-D-Ala-Gly-Phe-Leu-OH;L-Leucine, L-tyrosyl-D-alanylglycyl-L-phenylalanyl-;PO4D55T1IG;EINECS 265-291-0;NSC 374895;L-tyrosyl-D-alanylglycyl-L-phenylalanyl-L-leucine;N-(N-(N-(N-L-Tyrosyl-D-alanyl)glycyl)-L-phenylalanyl)-L-leucine;C29-H39-N5-O7;NSC-374895;(D-Ala2,Leu5)enkephalin;UNII-PO4D55T1IG;[D-Ala2]-Leu-Enkephalin;CHEMBL4539258;PENTAPEPTIDE-18 [INCI];SCHEMBL11396067;BDBM82090;(2S)-2-[[(2S)-2-[[2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid;1-5-(D-ALA2)-DYNORPHIN;HY-P0098;MFCD00076409;CS-5905;AC-31944;AS-76027;C76035;L-leucine, N-(N-(N-(N-L-Tyrosyl-D-alanyl)glycyl)-L-phenylalanyl)-;(2S,5S,11R,14S)-14-amino-5-benzyl-15-(4-hydroxyphenyl)-2-isobutyl-11-methyl-4,7,10,13-tetraoxo-3,6,9,12-tetraazapentadecan-1-oic acid

Chemical Property of [D-Ala2]leucine-enkephalin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 160-163.5 °C
• Refractive Index: 1.582
• Boiling Point: 991.9 °C at 760 mmHg
• PKA: 3.40±0.10(Predicted)
• Flash Point: 553.7 °C
• PSA: 199.95000
• Density: 1.257 g/cm³
• LogP: 2.48980
• Storage Temp.: −20°C
• Solubility.: DMF (Slightly), DMSO (Slightly)
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 15
• Exact Mass: 569.28494860
• Heavy Atom Count: 41
• Complexity: 885

Purity/Quality:

98% ^*data from raw suppliers

[D-Ala2]-Leucine enkephalin ≥97% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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)C(C)NC(=O)C(CC2=CC=C(C=C2)O)N
• Isomeric SMILES: C[C@H](C(=O)NCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC(C)C)C(=O)O)NC(=O)[C@H](CC2=CC=C(C=C2)O)N

Technology Process of [D-Ala2]leucine-enkephalin

There total 12 articles about [D-Ala2]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: 94.0%

H-L-Tyr(Mpt)-D-Ala-Gly-L-Phe-L-Leu-OH → D-Ala2-Leu5-enkephalin (60284-47-1,63631-40-3,64963-01-5,64963-05-9,64963-08-2,64975-66-2)

Guidance literature:

With sodium hydroxide; In methanol; at 0 ℃;

DOI:10.1246/bcsj.55.204

Reference yield: 47.0%

Nα-(tert-butoxycarbonyl)-2,Leu5>enkephalin (73965-71-6) → D-Ala2-Leu5-enkephalin (60284-47-1,63631-40-3,64963-01-5,64963-05-9,64963-08-2,64975-66-2)

Guidance literature:

With methoxybenzene; trifluoroacetic acid;

DOI:10.1021/jm00373a004

Reference yield:

(S)-2-[(S)-2-(2-{(R)-2-[(S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-propionylamino]-propionylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid benzyl ester → D-Ala2-Leu5-enkephalin (60284-47-1,63631-40-3,64963-01-5,64963-05-9,64963-08-2,64975-66-2)

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1248/cpb.45.1782

upstream raw materials:

2,4,5-didehydro-L-Leu⁵>Leu-enkephalin

N^α-(tert-butoxycarbonyl)-2,Leu⁵>enkephalin

N-benzyloxycarbonyl-O-benzyl-L-tyrosine

{(R)-2-[(S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-propionylamino]-propionylamino}-acetic acid methyl ester

Refernces

• 1、 Hasegawa, Hiroshi,Shinohara, Yoshihiko,Baba, Shigeo. "Synthesis of 2>Leu-enkephalin and 2,D-Leu5>Leu-enkephalin with High Specific Tritiated Activity in the Leucine Residue". . p. 2641 - 2644. Retrieved 2007/10/02.
• 2、 Ueki, Masaaki,Inazu, Toshiyuki. "Phosphinyl- and Phosphinothioylamino Acids and Peptides. VI. The Protection of the Hydroxyl Function in the Tyrosine Side-chain by the Dimethylphosphinothioyl Group". . p. 204 - 207. Retrieved 2007/10/02.