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B8385

Sigma-Aldrich

Bestatin hydrochloride

≥98% (HPLC)

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Synonym(s):
N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine hydrochloride
Empirical Formula (Hill Notation):
C16H24N2O4 · HCl
CAS Number:
Molecular Weight:
344.83
Beilstein/REAXYS Number:
4628066
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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

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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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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