Methyl leucylleucinate hydrochloride

Base Information

• Chemical Name: Methyl leucylleucinate hydrochloride
• CAS No.: 6491-83-4
• Molecular Formula: C₁₃H₂₆N₂O₃*ClH
• Molecular Weight: 294.822
• UNII: 76R0TP2LNW

Synonyms:6491-83-4;H-LEU-LEU-OME HCL;Leu-Leu-ome HCl;H-Leu-leu-OMe hydrochloride;Leu-Leu-ome hydrochloride;Methyl leucylleucinate HCl;76R0TP2LNW;L-Leucyl-L-Leucine methyl ester (hydrochloride);Leucylleucine methyl ester hydrochloride;methyl L-leucyl-L-leucinate hydrochloride;6491-83-4 (HCl);L-Leucine, L-leucyl-, methyl ester, hydrochloride (1:1);Methyl leucylleucinate hydrochloride;methyl (2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-4-methylpentanoate;hydrochloride;Methyl leucylleucinate (hydrochloride);RVXQFTNCULOWRV-ACMTZBLWSA-N;UNII-76R0TP2LNW;SCHEMBL17801790;H-Leu-leu-OMe (hydrochloride);MFCD00155477;L-Leucyl-L-leucine Methyl Ester HCl;AKOS030525138;BS-32671;PD018205;HY-129905;CS-0108388;hydrochloride l-leucyl-l-leucine methyl ester;L-Leucyl-L-Leucine methyl ester hydrochloride;E87015;METHYL (2S)-2-[(2S)-2-AMINO-4-METHYLPENTANAMIDO]-4-METHYLPENTANOATE HYDROCHLORIDE

Chemical Property of Methyl leucylleucinate hydrochloride

Chemical Property:

• Melting Point: 177-181°C
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 294.1710204
• Heavy Atom Count: 19
• Complexity: 277

Purity/Quality:

99% ^*data from raw suppliers

H-Leu-leu-OMehydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)CC(C(=O)NC(CC(C)C)C(=O)OC)N.Cl
• Isomeric SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)OC)N.Cl
• Description: L-Leucyl-L-Leucine methyl ester (LLME) is a lysosomal condensation product that has been reported to be cytotoxic towards natural killer cells and CD4+ and CD8+ T lymphocytes without affecting helper T cells and B cells. It has also been shown to induce death of monocytes, polymorphonuclear leukocytes, and myeloid tumor cells. Upon entry into cells via receptor-mediated endocytosis, LLME undergoes a condensation process catalyzed by dipeptidyl peptidase I (DPPI) in lysosomes. This condensation leads to lysosomal rupture and DNA fragmentation in DPPI-expressing immune cells such as cytotoxic T cells and natural killer cells.
• Uses: H-Leu-leu-OMe HCl

Technology Process of Methyl leucylleucinate hydrochloride

There total 4 articles about Methyl leucylleucinate hydrochloride 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: 98.1%

N-tert-butoxycarbonyl-L-leucyl-L-leucine methyl ester (15136-13-7,88621-07-2,127636-68-4,132769-33-6,15136-12-6) → ((S)-2-amino-4-methylpentanoyl)-L-leucine methyl ester hydrochloride (6491-83-4,63889-48-5,66190-38-3)

Guidance literature:

With hydrogenchloride; In methanol;

DOI:10.1002/anie.201208561

Reference yield:

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) → ((S)-2-amino-4-methylpentanoyl)-L-leucine methyl ester hydrochloride (6491-83-4,63889-48-5,66190-38-3)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; dicyclohexyl-carbodiimide / dichloromethane / 4 h / 0 - 20 °C

2: hydrogenchloride / 1,4-dioxane; water / 0.5 h / 20 °C

With hydrogenchloride; triethylamine; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane; water;

DOI:10.1016/j.bmc.2012.01.050

Reference yield:

methyl (L)-leucinate hydrochloride (7517-19-3) → ((S)-2-amino-4-methylpentanoyl)-L-leucine methyl ester hydrochloride (6491-83-4,63889-48-5,66190-38-3)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; dicyclohexyl-carbodiimide / dichloromethane / 4 h / 0 - 20 °C

2: hydrogenchloride / 1,4-dioxane; water / 0.5 h / 20 °C

With hydrogenchloride; triethylamine; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane; water;

DOI:10.1016/j.bmc.2012.01.050

upstream raw materials:

methanol

L-leucyl-L-leucine

N-tert-butoxycarbonyl-L-leucine

N-tert-butoxycarbonyl-L-leucyl-L-leucine methyl ester

Downstream raw materials:

N-carbobenzoxy-L-leucyl-L-leucyl-L-leucyl-L-leucyl-L-leucine methyl ester

N-(benzyloxycarbonyl)-L-leucyl-L-leucyl-L-leucine methyl ester

C₂₃H₃₈N₃O₇P

(3S,6S)-3,6-diisobutylpiperazine-2,5-dione

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