(Ala2)-Leu-Enkephalin

Base Information

• Chemical Name: (Ala2)-Leu-Enkephalin
• CAS No.: 60284-47-1
• Molecular Formula: C29H39N5O7
• Molecular Weight: 569.64900
• ChEMBL ID: CHEMBL266834
• DSSTox Substance ID: DTXSID60515342
• Nikkaji Number: J1.261.661I
• Wikidata: Q82376168
• Mol file: 60284-47-1.mol

Synonyms:(Ala2)-Leu-Enkephalin;60284-47-1;(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid;H-Tyr-Ala-Gly-Phe-Leu-OH;CHEMBL266834;SCHEMBL11683986;DTXSID60515342;NCGC00163682-01;PD063164;L-Tyrosyl-L-alanylglycyl-L-phenylalanyl-L-leucine

Chemical Property of (Ala2)-Leu-Enkephalin

Chemical Property:

• PSA: 213.91000
• LogP: 4.28740
• Storage Temp.: ?20°C
• 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:

99%+, ^*data from raw suppliers

(Ala2)-Leu-Enkephalin H-Tyr-Ala-Gly-Phe-Leu-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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 (Ala2)-Leu-Enkephalin

There total 21 articles about (Ala2)-Leu-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: 93.0%

H-L-Tyr(Dmp)-D-Ala-Gly-L-Phe-D-Leu-OH (108607-68-7) → [D-Ala2,D-Leu5] enkephalin (60284-47-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In diethyl ether; acetonitrile; for 1h; Ambient temperature;

DOI:10.1016/S0040-4039(00)84943-6

Reference yield: 57.85%

C17H13NO10S2(2-)*2Na(1+) + C21H21NO10S2(2-)*2Na(1+) + C24H19NO10S2(2-)*2Na(1+) + C24H19NO11S2(2-)*2Na(1+) + C18H15NO10S2(2-)*2Na(1+) → [D-Ala2,D-Leu5] enkephalin (60284-47-1)

Guidance literature:

C₂₁H₂₁NO₁₀S₂^(2-)*2Na⁽¹⁺⁾; With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethyl cyanoglyoxylate-2-oxime; In water; acetonitrile; at 20 ℃; for 0.75h;

With sodium hydroxide; In water; for 0.0833333h;

C₁₇H₁₃NO₁₀S₂^(2-)*2Na⁽¹⁺⁾; C₂₄H₁₉NO₁₀S₂^(2-)*2Na⁽¹⁺⁾; C₂₄H₁₉NO₁₁S₂^(2-)*2Na⁽¹⁺⁾; C₁₈H₁₅NO₁₀S₂^(2-)*2Na⁽¹⁺⁾; Further stages;

DOI:10.1002/anie.202003676

upstream raw materials:

H-L-Tyr(Dmp)-D-Ala-Gly-L-Phe-D-Leu-OH

N-tert-butoxycarbonyl-L-tyrosine benzyl ester

L-phenylalanyl-L-leucine tert-butyl ester

Boc-L-Tyr(Dmp)-OBzl

Refernces

• 1、 Kitagawa, Kouki,Mizobuchi, Noriko,Hama, Teruo,Hibi, Tohru,Konishi, Ryoji,Futaki, Shiroh. "Synthesis and antinociceptive activity of [D-Ala2]Leu-enkephalin derivatives conjugated with the adamantane moiety". . p. 1782 - 1787. Retrieved 2007/10/03.
• 2、 Ueki, Masaaki,Sano, Yoshiyuki,Sori, Ichiro,Shinozaki, Kozo,Oyamada,Hidekazu,Ikeda, Shigeru. "METHYLPHOSPHINYL (Dmp): A NEW PROTECTING GROUP OF TYROSINE SUITABLE FOR PEPTIDE SYNTHESIS BY USE OF BOC-AMINO ACIDS". . p. 4181 - 4184. Retrieved 2007/10/02.