65391-42-6

Basic information

• Product Name: BESTATIN HYDROCHLORIDE
• Synonyms: N-[(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTYRYL]-L-LEUCINE HYDROCHLORIDE;N-(3R-AMINO-2S-HYDROXY-1-OXO-4-PHENYLBUTYL)-L-LEUCINE, MONOHYDROCHLORIDE;[(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-L-LEUCINE HCL;[(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-L-LEUCINE HYDROCHLORIDE;(AMINO-2-HYDROXY-4-PHENYLBUTYRYL)-L-LEUCINE HYDROCHLORIDE;BESTATIN HCL;BESTATIN HYDROCHLORIDE;N-(2S,3R-3-AMINO-2-HYDROXY-4-PHENYLBUTY- RYL)-L-LEUCINE HCL
• CAS NO: 65391-42-6
• Molecular Formula: C₁₆H₂₄N₂O₄*ClH
• Molecular Weight: 344.83
• Product Categories: Pepetides;peptides;Bestatin;inhibitor
• Mol File: 65391-42-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 216-218 °C
• Boiling Point: 604.7 °C at 760 mmHg
• Flash Point: 319.5 °C
• Appearance: /
• Vapor Pressure: 1.06E-12mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: H2O: 25 mg/mL, clear, colorless
• Water Solubility: Soluble in water (4 mg/ml, warm), DMSO (>25 mg/ml), methanol, acetic acid, dimethyl formamide, and 100% ethanol.
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO, distilled water, or ethanol may be stored at -20° for up to 1 month.
• BRN: 4628066
• CAS DataBase Reference: BESTATIN HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BESTATIN HYDROCHLORIDE(65391-42-6)
• EPA Substance Registry System: BESTATIN HYDROCHLORIDE(65391-42-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 65391-42-6(Hazardous Substances Data)

Usage

Description

Bestatin HCl (65391-42-6) inhibits leucine aminopeptidase and aminopeptidases B and N. Inhibits leukotriene A4 hydrolase. Displays immunostimulant activity via activation of macrophages and T lymphocytes. Displays antitumor activity.

Uses

Different sources of media describe the Uses of 65391-42-6 differently. You can refer to the following data:
1. Bestatin Hydrochloride is an inhibitor of aminopeptidases, LAP3, and leukotriene A4 hydrolase. It is the salt form of Bestatin (B319500).
2. competitive aminopeptidase B inhibitor
3. Bestatin is an inhibitor of amino peptidases and a potent, irreversible inhibitor of LTA4 hydrolase. It inhibits the amino peptidase activity of LTA4 hydrolase with a Ki value of 201 nM. It offers promise as a novel analgesic because it protects endogenous opioid peptides against degradation. It does not inhibit carboxypeptidases.
4. Bestatin has been used as a protease inhibitor for the purification of his-tagged Tau protein.

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.

in vivo

in a mouse dorsal air sac assay, oral administration of bestatin (100-200 mg/kg/day) showed a significant inhibitory activity against the melanoma cell-induced angiogenesis. bestatin also inhibited the tube-like formation of human umbilical vein endothelial cells (huvecs). furthermore, after the orthotopic implantation of b16-bl6 melanoma cells into mice, bestatin administration (50-100 mg/kg/day, i.p) reduced the number of vessels oriented towards the established primary tumor mass on the dorsal side of mice [1].

References

1) Orning et al. (1991), Leukotriene A4 hydrolase. Inhibition by bestatin and intrinsic aminopeptidase activity establish its functional resemblance to metallohydrolase enzymes; J. Biol. Chem., 266 1375 2) Wang et al. (2010), The effect of different species aminopeptidase N structure on the activity screening of aminopeptidase N inhibitor; Biol. Pharm. Bull., 33 1658

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

Upstream product

• 246506-78-5 2-(3-tert-butoxycarbonylamino-2-oxo-4-phenylbutyrylamino)-4-methylpentanoic acid benzyl ester 
• 223763-80-2 bestatin trifluroacetate salt 
• 145902-56-3 tert-Butyl (4R,5S)-4-benzyl-5-(((2S)-1-(tert-butoxy)-4-methyl-1-oxopentan-2-yl)-carbamoyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 145872-15-7 (4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carboxylic acid ethyl ester 
• 7517-19-3 methyl (L)-leucinate hydrochloride 
• 100564-98-5 (4R,5S)-4-benzyl-2-oxo-5-oxazolidinecarboxylic acid 
• 247178-59-2 methyl (2S,3R)-3-(benzyloxycarbonyl)amino-2-formyloxy-4-phenylbutanoate 
• 247178-58-1 (R)-((4S,5R)-2-Benzyloxy-5-phenyl-4,5-dihydro-oxazol-4-yl)-hydroxy-acetic acid methyl ester 
• 247178-57-0 methyl (4S,5R)-2-benzyloxy-5-phenyloxazoline-4-acetate 
• 178897-35-3 (4S,5R)-4-methoxycarbonylmethyl-5-phenyloxazolidin-2-one 
• 124782-06-5 (2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 59969-65-2 (2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenyl-butanoic acid 
• 318499-01-3 benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-tert-butyldimethylsiloxy-4-phenyl-butanoyl]-L-leucinate 
• 246506-75-2 [1-benzyl-3-cyano-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-carbamic acid tert-butyl ester 

Relevant articles and documents

A practical diastereoselective synthesis of (?)-bestatin

Diastereoselective addition of nitromethane to Boc-D-Phe-H in the presence of sodium hydride in diethyl ether/hexane containing 15-crown-5 and subsequent N,O-protection with 2,2-dimethoxypropane gave trans-oxazolidine in a diastereomeric ratio of >16:1. T

Synthesis of (-)-bestatin and the Taxotere side-chain via nitroaldol reaction of (1R)-8-phenylmenthyl glyoxylate

The nitroaldol reaction of (1R)-8-phenylmenthyl glyoxylate 6 with 1-nitro-2-phenylethane or with phenylnitromethane led stereoselectively to adducts 4 and 12, which where then transformed into (-)-bestatin hydrochloride and the Taxotere side-chain in over

A new one-pot method for the synthesis of α-siloxyamides from aldehydes or ketones and its application to the synthesis of (-)-bestatin

(equation presented) A new one-pot method for the synthesis of α-siloxyamides is described. The three substrates, H-C(CN)2O-SiMe2t-Bu, aldehydes or ketones, and primary or secondary amines, are simply mixed in one portion in acetonitrile or ether; the α-siloxyamides are obtained within short peroids in excellent yields in many cases. As a demonstration of our method, the synthesis of (-)-bestatin was carried out.