An aminopeptidase inhibitor
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Amastatin (hydrochloride)

Item No. 16719

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(2S,3R)-3-amino-2-hydroxy-5-methyl-1-oxohexyl]-L-valyl-L-valyl-L-aspartic acid, monohydrochloride
CAS Number
100938-10-1
Molecular Formula
C21H38N4O8 • HCl
Formula Weight
511.0
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 2 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): 5 mg/ml
SMILES
CC(C)[C@H](NC([C@@H](NC([C@@H](O)[C@H](N)CC(C)C)=O)C(C)C)=O)C(N[C@@H](CC(O)=O)C(O)=O)=O.Cl
InChi Code
InChI=1S/C21H38N4O8.ClH/c1-9(2)7-12(22)17(28)20(31)25-16(11(5)6)19(30)24-15(10(3)4)18(29)23-13(21(32)33)8-14(26)27;/h9-13,15-17,28H,7-8,22H2,1-6H3,(H,23,29)(H,24,30)(H,25,31)(H,26,27)(H,32,33);1H/t12-,13+,15+,16+,17+;/m1./s1
InChi Key
GBDUPCKQTDKNLS-PORDUOSCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $37

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    1 mg

    $66

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    5 mg

    $209

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    10 mg

    $383

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    Product Description

    Amastatin is a slow, tight binding, competitive aminopeptidase (AP) inhibitor, first described as an inhibitor of human serum AP-A (glutamyl AP; IC50 = 0.54 µg/ml) but not of AP-B (arginine AP).1,2 It also inhibits AP-N (AP-M, alanyl AP; Ki = 20-200 nM), leucyl-cystinyl AP (Ki = 20-220 nM), and endoplasmic reticulum AP 1 (Ki = 41.8 µM).3,4,5,6 Amastatin is without effect on trypsin, papain, chymotrypsin, elastase, pepsin, or thermolysin.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Aoyagi, T., Tobe, H., Kojima, F., et al. Amastatin, an inhibitor of aminopeptidase A, produced by actinomycetes. J. Antibiot. (Tokyo) 31(6), 636-638 (1978).

    2. Wilkes, S.H., and Prescott, J.M. The slow, tight binding of bestatin and amastatin to aminopeptidases. The Journal of Biological Chemisty 260(24), 13154-13162 (1985).

    3. Rich, D.H., Moon, B.J., and Harbeson, S. Inhibition of aminopeptidases by amastatin and bestatin derivatives. Effect of inhibitor structure on slow-binding processes. J. Med. Chem. 27(4), 417-422 (1984).

    4. Harbeson, S.L., and Rich, D.H. Inhibition of aminopeptidases by peptides containing ketomethylene and hydroxyethylene amide bond replacements. J. Med. Chem. 32(6), 1378-1392 (1989).

    5. Grembecka, J., Mucha, A., Cierpicki, T., et al. The most potent organophosphorus inhibitors of leucine aminopeptidase. Structure-based design, chemistry, and activity. J. Med. Chem. 46(13), 2641-2655 (2003).

    6. Goto, Y., Tanji, H., Hattori, A., et al. Glutamine-181 is crucial in the enzymatic activity and substrate specificity of human endoplasmic-reticulum aminopeptidase-1. Biochem. J. 416(1), 109-116 (2008).