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

Base Information Edit

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

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

Supply Marketing:Edit

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Usbiological
Bestatin
5mg
$ 362.00

TRC
Bestatin
1g
$ 325.00

Tocris
Bestatin ≥98%(HPLC)
10
$ 158.00

TCI Chemical
Ubenimex
1G
$ 414.00

TCI Chemical
Ubenimex
250MG
$ 140.00

Sigma-Aldrich
Bestatin
10mg-m
$ 158.00

Sigma-Aldrich
Bestatin - CAS 58970-76-6 - Calbiochem Binds to cell surfaces and inhibits surface aminopeptidases, notably aminopeptidase B and leucine aminopeptidase.
10 mg
$ 146.15

Sigma-Aldrich
Bestatin [(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]-L-leucine hydrochloride
10 mg
$ 230.00

Sigma-Aldrich
N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine 97%
500mg
$ 298.00

Matrix Scientific
N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine 97%
1g
$ 365.00

Total 149 raw suppliers

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

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:

Pictogram(s):
Hazard Codes:
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

: 58970-76-6
bestatin

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