B8385

Bestatin hydrochloride

powder, ≥98% (HPLC)

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

Properties

• Product Name: Bestatin hydrochloride, ≥98% (HPLC)
• biological source: synthetic (organic)
• Quality Segment: 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

Description

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)