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M0398

Sigma-Aldrich

N-(Methoxysuccinyl)-Ala-Ala-Pro-Val-chloromethyl ketone

elastase inhibitor, powder, ≥98% (TLC)

Synonym(s):

N-(Methoxysuccinyl)-L-alanyl-L-alanyl-L-prolyl-L-valine chloromethylketone

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About This Item

Empirical Formula (Hill Notation):
C22H35ClN4O7
CAS Number:
65144-34-5
Molecular Weight:
502.99
Beilstein/REAXYS Number:
6167019
MDL number:
MFCD00077136
UNSPSC Code:
12352202
PubChem Substance ID:
24896552
NACRES:
NA.77

product name

N-(Methoxysuccinyl)-Ala-Ala-Pro-Val-chloromethyl ketone, elastase inhibitor

assay

≥98% (TLC)

form

powder

mp

159 °C

solubility

methanol: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

COC(=O)CCC(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)CCl

InChI

1S/C22H35ClN4O7/c1-12(2)19(16(28)11-23)26-21(32)15-7-6-10-27(15)22(33)14(4)25-20(31)13(3)24-17(29)8-9-18(30)34-5/h12-15,19H,6-11H2,1-5H3,(H,24,29)(H,25,31)(H,26,32)/t13-,14-,15-,19-/m0/s1

InChI key

PJGDFLJMBAYGGC-XLPNERPQSA-N

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General description

N-(Methoxysuccinyl)-Ala-Ala-Pro-Val-chloromethyl ketone is a tetrapeptide, cell-permeable and non-cytotoxic inhibitor.

Application

N-(Methoxysuccinyl)-Ala-Ala-Pro-Val-chloromethyl ketone has been used as an elastase specific inhibitor.

Biochem/physiol Actions

N-(Methoxysuccinyl)-Ala-Ala-Pro-Val-chloromethyl ketone acts as a competitive inhibitor of human leukocyte elastase (HLE).
Irreversible inhibitor of human leukocyte and neutrophil elastase.

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)

Certificates of Analysis (COA)

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V S Carl et al.
Immunopharmacology, 33(1-3), 325-329 (1996-06-01)
Bradykinin (BK) is a potent inflammatory mediator, which can release other inflammatory mediators by interacting with bradykinin B1 and B2 receptors. The role of kinins in regulating human PMN elastase release was studied. BK induced elastase release 5-fold over basal
Prevention of elastase-induced experimental emphysema by oral administration of a synthetic elastase inhibitor.
A Janoff et al.
The American review of respiratory disease, 121(6), 1025-1029 (1980-06-01)
Proteolytic cleavage of annexin 1 by human leukocyte elastase
Rescher U, et al.
Biochimica et Biophysica Acta - Molecular Cell Research, 1763(11), 1320-1324 (2006)
L A Smedly et al.
The Journal of clinical investigation, 77(4), 1233-1243 (1986-04-01)
The neutrophil has been implicated as an important mediator of vascular injury, especially after endotoxemia. This study examines neutrophil-mediated injury to human microvascular endothelial cells in vitro. We found that neutrophils stimulated by formyl-methionyl-leucyl-phenylalanine (FMLP), the complement fragment C5a, or
Takeshi Kawamura et al.
Microbiology and immunology, 46(3), 225-230 (2002-05-15)
Carboxypeptidase R (EC 3.4.17.20; CPR) is an unstable basic carboxypeptidase found in fresh serum in addition to carboxypeptidase N (CPN) which is a stable enzyme. CPR in fresh serum is generated from its zymogen (proCPR) during coagulation by trypsin-like enzymes
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Articles

Elastase

Enzyme Explorer Product Application Index for Elastase. Leukocyte elastase is a 29KDa serine endoprotease of the Proteinase S1 Family. It exists as a single 238 amino acid-peptide chain with four disulfide bonds.

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