Dadle

Base Information

• Chemical Name: Dadle
• CAS No.: 63631-40-3
• Molecular Formula: C29H39 N5 O7
• Molecular Weight: 569.658
• UNII: HB4QD9GL6F
• Nikkaji Number: J246.144G
• Wikipedia: DADLE
• Wikidata: Q424905
• Metabolomics Workbench ID: 151958
• ChEMBL ID: CHEMBL340032
• Mol file: 63631-40-3.mol

Synonyms:2 Alanyl Leucine Enkephalin;2-Alanyl-Leucine Enkephalin;5 Leucine 2 Alanine Enkephalin;5-Leucine-2-Alanine Enkephalin;BW 180C;BW-180C;BW180C;D-Ala(2)-D-Leu(5)-Enkephalin;DADLE;Enkephalin, 2-Alanyl-Leucine;Enkephalin, 5-Leucine-2-Alanine;Enkephalin, Leucine 2 Alanine;Enkephalin, Leucine-2-Alanine;Enkephalin-2-Alanine, Leucine;Enkephalin-Leu,Ala(2);Leu Enkephalin 2 Ala;Leu-Enkephalin-2-Ala;Leucine Enkephalin 2 Alanine;Leucine Enkephalin-2-Alanine;Leucine-2-Alanine Enkephalin

Chemical Property of Dadle

Chemical Property:

• Melting Point: >167°C (dec.)
• Boiling Point: 991.9±65.0 °C(Predicted)
• PKA: 3.40±0.10(Predicted)
• PSA: 199.95000
• Density: 1.257±0.06 g/cm3(Predicted)
• LogP: 2.48980
• Storage Temp.: -15°C
• Solubility.: DMSO (Slightly), Methanol (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:

99% ^*data from raw suppliers

DADLE ^*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 Dadle

There total 19 articles about Dadle 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:

AOA-DADLE → formaldehyd (50-00-0,30525-89-4,61233-19-0) + carbon dioxide (124-38-9,18923-20-1) + (R)-2-[(S)-2-(2-{(R)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-propionylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid (63631-40-3)

Guidance literature:

rat liver homogenate; In water; dimethyl sulfoxide; at 37 ℃; for 15h; pH=7.4; Further Variations:; Catalysts; with esterase inhibitor; Enzyme kinetics;

DOI:10.1023/A:1018854308829

upstream raw materials:

2,4,5-didehydro-D-Leu⁵>Leu-enkephalin

(Z)-(7R,10S,16R,19S)-10-Benzyl-19-(4-hydroxy-benzyl)-7-isobutyl-16-methyl-7,8,10,11,13,14,16,17,19,20-decahydro-5-oxa-8,11,14,17,20-pentaaza-benzocyclohenicosene-6,9,12,15,18,21-hexaone

Fmoc-4,5-didehydro-DL-leucine

Fmoc-4,5-didehydro-D,L-leucine Benzotriazole Ester

Refernces

• 1、 Gudmundsson, Olafur S.,Pauletti, Giovanni M.,Wang, Wei,Shan, Daxian,Zhang, Huijuan,Wang, Binghe,Borchardt, Ronald T.. "Coumarinic acid-based cyclic prodrugs of opioid peptides that exhibit metabolic stability to peptidases and excellent cellular permeability". . p. 7 - 15. Retrieved 2007/10/03.
• 2、 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.