Cyclo(L-leucyl-L-tryptophyl)

Base Information

• Chemical Name: Cyclo(L-leucyl-L-tryptophyl)
• CAS No.: 15136-34-2
• Molecular Formula: C₁₇H₂₁N₃O₂
• Molecular Weight: 299.373
• DSSTox Substance ID: DTXSID10164768
• Nikkaji Number: J2.847.345A
• Wikidata: Q83033837
• ChEMBL ID: CHEMBL365348
• Mol file: 15136-34-2.mol

Synonyms:cyclo(L-leucyl-L-tryptophyl);cyclo(Leu-Trp)

Chemical Property of Cyclo(L-leucyl-L-tryptophyl)

Chemical Property:

• Vapor Pressure: 4.89E-16mmHg at 25°C
• Melting Point: 217.28 °C
• Boiling Point: 635.2°Cat760mmHg
• Flash Point: 337.9°C
• PSA: 80.97000
• Density: 1.182g/cm³
• LogP: 2.29150
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 299.16337692
• Heavy Atom Count: 22
• Complexity: 438

Purity/Quality:

99%+, ^*data from raw suppliers

Cyclo(L-Leu-L-Trp) ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC1C(=O)NC(C(=O)N1)CC2=CNC3=CC=CC=C32
• Isomeric SMILES: CC(C)C[C@H]1C(=O)N[C@H](C(=O)N1)CC2=CNC3=CC=CC=C32

Technology Process of Cyclo(L-leucyl-L-tryptophyl)

There total 10 articles about Cyclo(L-leucyl-L-tryptophyl) 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: 78.0%

Fmoc-Leu-OH (35661-60-0) + (S)-tryptophan methyl ester hydrochloride (7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8) → Cyclo(L-leucyl-L-tryptophyl) (56941-94-7,75557-46-9,99095-60-0,15136-34-2)

Guidance literature:

Fmoc-Leu-OH; (S)-tryptophan methyl ester hydrochloride; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

With piperidine; In acetonitrile; for 22h;

DOI:10.1039/C7CC00555E

Reference yield: 60.0%

Cbz-Trp-Leu-OMe (2419-36-5) → Cyclo(L-leucyl-L-tryptophyl) (56941-94-7,75557-46-9,99095-60-0,15136-34-2)

Guidance literature:

Cbz-Trp-Leu-OMe; With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 0.666667h;

In methanol; for 48h; Reflux;

DOI:10.3987/COM-18-S(F)42

Reference yield: 55.0%

N-t-butyloxycarbonyl-L-leucyl-L-tryptophan methyl ester (141595-69-9,128254-47-7) → Cyclo(L-leucyl-L-tryptophyl) (56941-94-7,75557-46-9,99095-60-0,15136-34-2)

Guidance literature:

With hydrogenchloride; In water; ethyl acetate; at 50 ℃; for 24h;

DOI:10.1002/ejoc.201600444

upstream raw materials:

N-tert-butoxycarbonyl-L-tryptophan-L-leucine methylester

(S)-Leu-OMe

Cbz-Trp-Leu-OMe

N-carbobenzyloxy-L-tryptophane

Downstream raw materials:

C₂₂H₂₉N₃O₂

(2S,10aS,5aS,4aS)-5a-(1,1-dimethylprop-2-enyl)-2-(2-methylpropyl)-1,2,3,4,4a,5,5a,10a-octahydro-10H-pyrazino[1',2':1,2]pyrrolo[4,5-b]indole-1,4-dione

(3S,6S)-(-)-6-(1-benzoyloxyindol-3-ylmethyl)-3-isobutyl-2,5-piperazinedione

Refernces

• 1、 Fukui, Yoshikazu,Kobayashi, Tetsuya,Kawasaki, Toshiya,Yamada, Fumio,Somei, Masanori. "A [3,3] sigmatropic and novel ipso [3,3] sigmatropic rearrangement of 1-hydroxyindole chemistry". . p. 465 - 483. Retrieved 2019/08/02.
• 2、 Furukawa, Tadashi,Akutagawa, Takashi,Funatani, Hitomi,Uchida, Toshikazu,Hotta, Yoshihiro,Niwa, Masatake,Takaya, Yoshiaki. "Cyclic dipeptides exhibit potency for scavenging radicals". . p. 2002 - 2009. Retrieved 2012/05/04.