(2R)-2-[[(2S,3R)-3-amino-2-hydroxy-4-phenyl-butanoyl]amino]-4-methyl-pentanoic acid

Base Information

• Chemical Name: (2R)-2-[[(2S,3R)-3-amino-2-hydroxy-4-phenyl-butanoyl]amino]-4-methyl-pentanoic acid
• CAS No.: 58970-76-6
• Molecular Formula: C16H24N2O4
• Molecular Weight: 308.378
• Hs Code.: 29242998
• DSSTox Substance ID: DTXSID4048430
• Wikidata: Q27075116
• Pharos Ligand ID: PC6C6QG16XWN
• Metabolomics Workbench ID: 68509
• ChEMBL ID: CHEMBL476869
• Mol file: 58970-76-6.mol

Synonyms:Bestatin (TN);CHEBI:3070;UPCMLD-DP116;CHEMBL476869;SureCN25971;Ubenimex (JP16/INN);Ubenimex (JP17/INN);SCHEMBL25971;GTPL5151;DTXSID4048430;UPCMLD-DP116:001;(2R)-2-[[(2S,3R)-3-amino-2-hydroxy-4-phenyl-butanoyl]amino]-4-methyl-pentanoic acid;CHEBI:140702;BDBM50010142;ZINC01532730;AKOS026750073;NCGC00161660-01;C00732;D00087;Q27075116;(2R)-2-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido]-4-methylpentanoic acid

Chemical Property of (2R)-2-[[(2S,3R)-3-amino-2-hydroxy-4-phenyl-butanoyl]amino]-4-methyl-pentanoic acid

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.8E-15mmHg at 25°C
• Melting Point: 245 °C (dec.)(lit.)
• Refractive Index: 1.557
• Boiling Point: 604.7 °C at 760 mmHg
• PKA: 8.1, 3.1(at 25℃)
• Flash Point: 319.5 °C
• PSA: 112.65000
• Density: 1.197 g/cm³
• LogP: 1.62400
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Acid (Slightly, Sonicated), DMSO (Slightly, Heated), Methanol (Slightly,
• Water Solubility.: Soluble in water (<1 25), DMSO (2 mg/ml), methanol (5 mg/ml), 1eq. NaOH (50 mM), ethanol (<1 mg/ml at 25°C), acetic acid,
• XLogP3: -1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 308.17360725
• Heavy Atom Count: 22
• Complexity: 367

Purity/Quality:

98.5%min ^*data from raw suppliers

Bestatin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)O)NC(=O)C(C(CC1=CC=CC=C1)N)O
• Isomeric SMILES: CC(C)C[C@H](C(=O)O)NC(=O)[C@H]([C@@H](CC1=CC=CC=C1)N)O
• Description: Bestatin is an aminopeptidase inhibitor originally isolated from S. olivoreticuli. It inhibits aminopeptidase B (IC50 = 0.05 μg/ml), aminopeptidase N (IC50 = 16.9 μM), leucine aminopeptidase (IC50 = 0.01 μg/ml), and the aminopeptidase activity of leukotriene A4 (LTA4) hydrolase (Kapp = 172 nM). It is selective for these aminopeptidases over aminopeptidase A, trypsin, chymotrypsin, elastase, papain, pepsin, and thermolysin. Bestatin inhibits the production of LTB4 in erythrocytes when used at a concentration of 70 μM. It increases the expression of Akt, inhibits proliferation, migration, and invasion, and induces autophagy and apoptosis in 5637 bladder cancer cells. Bestatin (5 and 15 mg/kg) decreases serum levels of LTB4 and reduces tumor growth in a patient-derived xenograft (PDX) mouse model of colorectal cancer.
• Uses: Ubenimex (also known as bestatin) is a competitive aminopeptidase B inhibitor with an IC50 of 100 mg/ml for K562 cells. Proliferation of all the cell lines except KG1 was inhibited by bestatin. P39/TSU, HL60 and U937 were highly sensitive, with 50% growth inhibitory concentration. It is useful in the treatment of non-lymphocytic leukemia. In other types of cancers ubenimex added to radiotherapy or chemotherapy following surgery significantly inmases survival time through immunopotentiation. It is being studied for use in the treatment of acute myelocytic leukemia. Bestatin is "pseudo"-dipeptide isolated from Strepotmyces olivreticuli in 1976. Bestatin is a potent aminopeptidase B inhibitor with no carboxypeptidase activity. Bestatin acts as an immunomodulator by activating macrophages and T lymphocytes. Bestatin also exhibits good antitumour activity and is has been investigated in clinical trials.

Technology Process of (2R)-2-[[(2S,3R)-3-amino-2-hydroxy-4-phenyl-butanoyl]amino]-4-methyl-pentanoic acid

There total 73 articles about (2R)-2-[[(2S,3R)-3-amino-2-hydroxy-4-phenyl-butanoyl]amino]-4-methyl-pentanoic acid 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: 98.9%

N-[(2S,3R)-4-phenyl-3-nitro-2-hydroxybutyryl]-L-leucine → bestatin (58970-76-6)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; at 20 - 50 ℃; under 9000.9 - 22502.3 Torr; Solvent; Reagent/catalyst; Temperature; Autoclave;

Reference yield: 90.0%

C28H38N2O6 → bestatin (58970-76-6)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 2h;

Reference yield: 86.0%

N-<(2S,3S)-3-azido-2-hydroxy-4-phenylbutanoyl>-L-leucine benzyl ester (121445-53-2) → bestatin (58970-76-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 48h; under 760 Torr;

DOI:10.1021/jo00278a050

upstream raw materials:

benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate

N-<(2S,3S)-3-azido-2-hydroxy-4-phenylbutanoyl>-L-leucine benzyl ester

(S-(R*,S*))-N-(3-amino-2-hydroxy-4-phenylbutyroyl)-L-leucine

(S)-2-((R)-3-Benzyloxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-4-methyl-pentanoic acid benzyl ester

Downstream raw materials:

nitrobestatin

(S)-2-{(2S,3R)-3-[(9H-fluoren-9-yl)methoxy]carbonylamino-2-hydroxy-4-phenylbutanamido}-4-methylpentanoic acid

methyl (2S)-2-(((2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl)amino)-4-methylpentanoate

(S)-methyl 2-((2S,3R)-3-acetamido-2-acetoxy-4-(4-bromophenyl)butanamido)-4-methylpentanoate

Refernces

Design and synthesis of estrogen receptor degradation inducer based on a protein knockdown strategy

10.1016/j.bmcl.2011.11.086

The study explores the development of compounds that can selectively degrade estrogen receptor alpha (ERα) in breast cancer cells. The researchers designed and synthesized three hybrid molecules, designated as compounds 5, 6, and 7, which are composed of a tamoxifen derivative and bestatin (BS), an inhibitor of the cellular inhibitor of apoptosis protein 1 (cIAP1). These molecules are engineered to cross-link ERα and cIAP1, thereby inducing ubiquitylation and subsequent proteasomal degradation of ERα. The tamoxifen derivative serves as a ligand to bind specifically to ERα, while the BS moiety binds to cIAP1 to facilitate the degradation process. The study demonstrates that compounds 5, 6, and 7 effectively reduce ERα levels in MCF-7 breast cancer cells in a dose-dependent manner, with their activity being inhibited by the proteasome inhibitor MG132, confirming the proteasomal degradation pathway. These findings suggest that these molecules could serve as potential therapeutic agents for breast cancer by selectively degrading ERα, a protein often overexpressed in breast cancer tissues.