Methyl 2-amino-4-methylpentanoate hydrochloride

Base Information

• Chemical Name: Methyl 2-amino-4-methylpentanoate hydrochloride
• CAS No.: 7517-19-3
• Molecular Formula: C7H16ClNO2
• Molecular Weight: 181.663
• Hs Code.: 29224995
• European Community (EC) Number: 228-681-1
• NSC Number: 522846,522233,32110
• Mol file: 7517-19-3.mol

Synonyms:6322-53-8;H-DL-Leu-OMe HCl;methyl 2-amino-4-methylpentanoate hydrochloride;H-DL-Leu-OMe.HCl;H-DL-Leu-Ome-HCl;H-D-LEU-OME HCL;methyl 2-amino-4-methylpentanoate;hydrochloride;Methyl DL-leucinate hydrochloride;Methyl L-leucinate HCl;H-DL-Leu-OMe hydrochloride;EINECS 231-375-0;MFCD00066115;dl-leucine methyl ester hydrochloride;H-L-LEU-OME HCL;H-D-Leu-OMe . HCl;H-D-Leu-OMe hydrochloride;SCHEMBL355415;DODCBMODXGJOKD-UHFFFAOYSA-N;NSC32110;MFCD00067541;NSC-32110;NSC522233;NSC522846;AKOS008030231;FD21914;NSC 522233;NSC-522233;NSC-522846;H-DL-Leu-OMe hydrochloride, AldrichCPR;Leucine,methyl ester,hydrochloride(1:1);AS-49240;SY037977;Leucine methyl ester, hydrochloride (1:1);AM20100563;CS-0213107;FT-0625461;FT-0627935;EN300-07724;A838338;methyl 2-azanyl-4-methyl-pentanoate hydrochloride;Z56960272;2-amino-4-methylpentanoic acid methyl ester hydrochloride;Dimethylaminonaphthalene-5-sulfonamidoethyltrimethylammoniumperchlorate

Chemical Property of Methyl 2-amino-4-methylpentanoate hydrochloride

Chemical Property:

• Appearance/Colour: Crystalline
• Vapor Pressure: 1.56mmHg at 25°C
• Melting Point: 151-153 °C(lit.)
• Refractive Index: 13 ° (C=2, H2O)
• Boiling Point: 169.2 °C at 760 mmHg
• Flash Point: 42.7 °C
• PSA: 52.32000
• Density: 0.955 g/cm³
• LogP: 2.03510
• Storage Temp.: 0-6°C
• Sensitive.: Hygroscopic
• Solubility.: H2O: 50 mg/mL, clear, colorless
• Water Solubility.: soluble
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 181.0869564
• Heavy Atom Count: 11
• Complexity: 112

Purity/Quality:

99% ^*data from raw suppliers

L-Leucine methyl ester hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CC(C(=O)OC)N.Cl
• Uses: L-Leucine methyl ester is a protected form of L-Leucine (L330110). L-Leucine is an essential amino acid that induces a sharp decrease in blood glucose levels in individuals with idiopathic familial hypoglycemia, but has no known effects on normal, healthy individuals. L-Leucine also acts as an Isoleucine (I820210) antagonist in the rat, causing delays in growth, and is a potential tumour promoter of bladder cancer.

Technology Process of Methyl 2-amino-4-methylpentanoate hydrochloride

There total 21 articles about Methyl 2-amino-4-methylpentanoate 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: 100.0%

methanol (67-56-1) + (R)-leucine (328-38-1,21675-61-6,25248-98-0,70-45-1) → (R)-leucine methyl ester hydrochloride (5845-53-4,6322-53-8,7517-19-3)

Guidance literature:

With sulfuryl dichloride; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/anie.201603288

Reference yield: 100.0%

methanol (67-56-1) + L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) → methyl (L)-leucinate hydrochloride (7517-19-3)

Guidance literature:

methanol; With thionyl chloride; for 1h; Cooling with ice;

L-leucine; at 20 - 66 ℃; for 6.5h;

Reference yield: 100.0%

Alloc-Leu-OMe (128369-74-4) → methyl (L)-leucinate hydrochloride (7517-19-3)

Guidance literature:

With triethylsilane; chloroform; palladium on activated charcoal; In methanol; for 0.0833333h;

DOI:10.1021/jo0706123

upstream raw materials:

methanol

L-leucine

(S)-2-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-4-methyl-pentanoic acid methyl ester

Alloc-Leu-OMe

Downstream raw materials:

N-benzyloxycarbonylglycyl-L-leucine methyl ester

Cbz-L-Leu-L-Leu-OMe

Cbz-L-Phe-L-Leu-OMe

(S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)-4-methylpentanoate

Refernces

Structural basis for the potent calpain inhibitory activity of peptidyl α-ketoacids

10.1021/jm800182c

This research aimed to explore the structural basis for the potent calpain inhibitory activity of a series of peptidyl R-ketoacids and R-ketoesters, focusing on their potential as therapeutic agents for diseases associated with calpain, a family of calcium-dependent cysteine proteases. The study synthesized and tested these compounds, revealing that R-ketoacids were more effective inhibitors of μ-calpain than the corresponding R-ketoesters, with the carboxylic acid group being crucial for potent inhibition. The most potent inhibitor, R-ketoacid 2e, was found to be 150-fold more potent than its methyl ester derivative 1e. Docking studies suggested that hydrogen bonding interactions, potential ionic interactions with active site residues, and the placement of a planar N-terminal capping group into the S3 pocket of the enzyme were key factors in the inhibitory activity. The chemicals used in the synthesis included L-leucine methyl ester hydrochloride, various carboxylic acids, EDC/HOBT as coupling agents, and Dess-Martin reagent for oxidation steps, among others. The study concluded that the structural basis for the potent calpain inhibitory activity of peptidyl R-ketoacids involves a network of hydrogen bonding interactions and the possibility for ionic interaction between the inhibitor and active site residues of the enzyme, with large planar aromatic groups as the N-terminal capping substituent being preferred for potent inhibition.

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