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Merck
CN

10874515001

Roche

Bestatin

95% (HPLC), crystalline powder, suitable for protein purification

Synonym(s):

Bestatin hydrochloride, N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine hydrochloride, 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
PubChem Substance ID:
UNSPSC Code:
12352204
Beilstein/REAXYS Number:
4628066
MDL number:
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description

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

assay

95% (HPLC)

form

crystalline powder

packaging

pkg of 10 mg

manufacturer/tradename

Roche

storage condition

protect from light

technique(s)

protein purification: suitable

mp

195-205 °C

solubility

water: soluble 25 g/L, alcohol: soluble 5 g/L

λmax

255-260 nm at 1 N in hydrochloric acid

shipped in

wet ice

storage temp.

2-8°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

Application

Bestatin has been used as a protease inhibitor for the purification of his-tagged Tau protein.

Biochem/physiol Actions

Bestatin exhibits anti-angiogenic property and inhibits new blood vessel formation at the early stage of tumor growth and in the metastatic sites.
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

Working concentration: 40 μg/ml (130 μM)
Working solution: Recommended solvents are 1 M HCl, methanol or 0.15 M NaCl.
Soluble to 20 mg/ml in 1 M HCl, 5 mg/ml in methanol, and 1 mg/ml in 0.15 M NaCl. Do not store in HCl.
For best results, use a stock solution of 2–5 mg/ml in methanol.
Storage conditions (working solution): -15 to -25 °C
Avoid repeated freezing!
Soluble to 20 mg/ml in 1 M HCl, 5 mg/ml in methanol, and 1 mg/ml in 0.15 M NaCl. Do not store in HCl. Roche recommends preparing a stock solution of 2 to 5 mg/ml in methanol.
Solutions are stable for 6 months when stored in aliquots at -15 to -25 °C.
Store at 2 to 8 °C. (Store dry!)

Other Notes

For life science research only. Not for use in diagnostic procedures.

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

涉药品监管产品

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Anti-tumor angiogenesis effect of aminopeptidase inhibitor bestatin against B16-BL6 melanoma cells orthotopically implanted into syngeneic mice.
Aozuka Y, et al.
Cancer letters, 216(1), 35-42 (2004)
Production of recombinant tau oligomers in vitro.
Methods in Cell Biology, 141, 45-64 (2017)
G Mathé
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 45(2-3), 49-54 (1991-01-01)
Bestatin, the dipeptide N-((2S, 3R)-3-amino-2-hydroxy-4-phenyl butanyl) L-leucine is a leucine aminopeptidase and aminopeptidase-B inhibitor. It exerts a direct stimulating effect on lymphocytes (and monocytes) via its fixation on cell surface leucine-aminopeptidase, and an indirect effect on monocytes (and lymphocytes) via
Zheng-Zhao Liu et al.
Autophagy, 17(10), 2766-2782 (2020-11-05)
Senile osteoporosis (OP) is often concomitant with decreased autophagic activity. OPTN (optineurin), a macroautophagy/autophagy (hereinafter referred to as autophagy) receptor, is found to play a pivotal role in selective autophagy, coupling autophagy with bone metabolism. However, its role in osteogenesis

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