B8385
Bestatin hydrochloride
powder, ≥98% (HPLC)
Synonym(s):
N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine hydrochloride
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About This Item
Empirical Formula (Hill Notation):
C16H24N2O4 · HCl
CAS Number:
Molecular Weight:
344.83
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352202
MDL number:
Beilstein/REAXYS Number:
4628066
Product Name
Bestatin hydrochloride, ≥98% (HPLC)
biological source
synthetic (organic)
Quality Level
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)
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Product Information Sheet
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
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
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