Skip to Content
Merck

B8385

Bestatin hydrochloride

powder, ≥98% (HPLC)

Synonym(s):

N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine hydrochloride

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C16H24N2O4 · HCl
CAS Number:
65391-42-6
Molecular Weight:
344.83
NACRES:
NA.77
PubChem Substance ID:
24278278
UNSPSC Code:
12352202
MDL number:
MFCD00058004
Beilstein/REAXYS Number:
4628066

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

Bestatin hydrochloride, ≥98% (HPLC)

biological source

synthetic (organic)

Quality Level

300

assay

≥98% (HPLC)

form

powder

mp

216 °C

solubility

water: 25 mg/mL, clear to very slightly hazy, colorless

antibiotic activity spectrum

neoplastics

mode of action

enzyme | inhibits

storage temp.

−20°C

SMILES string

O=C(N[C@@H](CC(C)C)C(O)=O)[C@@H](O)[C@H](N)CC1=CC=CC=C1.Cl[H]

InChI

1S/C16H24N2O4.ClH/c1-10(2)8-13(16(21)22)18-15(20)14(19)12(17)9-11-6-4-3-5-7-11;/h3-7,10,12-14,19H,8-9,17H2,1-2H3,(H,18,20)(H,21,22);1H/t12-,13+,14+;/m1./s1

InChI key

XGDFITZJGKUSDK-UDYGKFQRSA-N

General description

Chemical structure: amino acid derivatives

Biochem/physiol Actions

A metalloprotease inhibitor selective for aminopeptidase. Bestatin is a competitive and specific inhibitor of leucine aminopeptidase, aminopeptidase B, and triamino peptidase. It inhibits aminopeptidase B at 60 nM (using arginine-β-naphthylamide as substrate) and leucine aminopeptidase at 20 nM (leucine-β-naphthylamide as substrate). It showed no inhibition of aminopeptidase A, trypsin, chymotrypsin, elastase, papain, pepsin, or themolysin. It offers promise as a novel analgesic because it protects endogenous opioid peptides against degradation.

Preparation Note

Solubility testing in water at 25 mg/ml yields a clear solution. Stock solutions at 1 mM are expected to be stable at least one month stored at -20 °C.

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

B8385-BULK: + B8385-.5MG: + B8385-5MG-KC: + B8385-25MG: + B8385-5MG: + B8385-10MG: + B8385-1MG: + B8385-100MG: + B8385-VAR:

jan

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000522619
0000538414
0000522619
0000538414
0000522618

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Hye Cheong Koo et al.
International journal of molecular sciences, 22(8) (2021-05-01)
It has been shown previously that a novel tetrapeptide, Arg-Leu-Tyr-Glu (RLYE), derived from human plasminogen inhibits vascular endothelial growth factor (VEGF)-induced angiogenesis, suppresses choroidal neovascularization in mice by an inhibition of VEGF receptor-2 (VEGFR-2) specific signaling pathway. In this study
A Taylor
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 7(2), 290-298 (1993-02-01)
Aminopeptidases catalyze the cleavage of amino acids from the amino terminus of protein or peptide substrates. They are widely distributed throughout the animal and plant kingdoms and are found in many subcellular organelles, in cytoplasm, and as membrane components. Several
Tina S Skinner-Adams et al.
Journal of medicinal chemistry, 50(24), 6024-6031 (2007-10-27)
Previous studies have pinpointed the M17 leucyl aminopeptidase of Plasmodium falciparum (PfLAP) as a target for the development of new antimalarials. This metallo-exopeptidase functions in the terminal stages of hemoglobin digestion and is inhibited by bestatin, a natural analog of
Michael B Harbut et al.
Proceedings of the National Academy of Sciences of the United States of America, 108(34), E526-E534 (2011-08-17)
Malaria causes worldwide morbidity and mortality, and while chemotherapy remains an excellent means of malaria control, drug-resistant parasites necessitate the discovery of new antimalarials. Peptidases are a promising class of drug targets and perform several important roles during the Plasmodium
Anna L Epp et al.
Scientific reports, 9(1), 9721-9721 (2019-07-07)
The Pannexin 1 (Panx1) ion and metabolite channel is expressed in a wide variety of cells where it regulates a number of cell behaviours including proliferation and differentiation. Panx1 is expressed on the cell surface as well as intracellular membranes.
View All Related Papers

Articles

ReadyShield Phosphatase and Protease Inhibitor Cocktail FAQ

ReadyShield® phosphatase and protease inhibitor cocktail FAQ for sample protection in a variety of cell types and tissue extracts, including mammalian, plant, and microbial samples. Our ReadyShield® Protease Inhibitor Cocktail is a non-freezing solution that contains inhibitors with a broad specificity for serine, cysteine, acid proteases and aminopeptidases.

Related Content

Product Information Sheet - B8385

Product Information Sheet

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service