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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:
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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This Item
D2141A1276C3909
Bestatin hydrochloride ≥98% (HPLC)

Sigma-Aldrich

B8385

Bestatin hydrochloride

D-Cycloserine synthetic

Sigma-Aldrich

C3909

D-Cycloserine

assay

≥98% (HPLC)

assay

>95% (TLC)

assay

≥97% (HPLC)

assay

-

form

powder

form

crystalline

form

powder

form

powder

mp

216 °C

mp

145 °C

mp

202-205 °C

mp

147 °C (dec.) (lit.)

solubility

water: 25 mg/mL, clear to very slightly hazy, colorless

solubility

-

solubility

methanol: 1 mM (Stock solution stable for 1 month at −20 °C. Working solution stable for 1 day.)

solubility

water: 50 mg/mL, clear, colorless to light yellow

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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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
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Malaria causes worldwide morbidity and mortality, and while chemotherapy remains an excellent means of malaria control, drug-resistant parasites necessitate the discovery of new antimalarials. Peptidases are a promising class of drug targets and perform several important roles during the Plasmodium
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