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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:
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

Quality Level

200

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 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

Certificates of Analysis (COA)

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R L Stein et al.
Biochemistry, 25(19), 5414-5419 (1986-09-23)
The mechanism of inactivation of human leukocyte elastase (HLE) by the chloromethyl ketone MeOSuc-Ala-Ala-Pro-Val-CH2Cl was investigated. The dependence of the first-order rate constant for inactivation on concentration of chloromethyl ketone is hyperbolic and suggests formation of a reversible "Michaelis complex"
E J Bates et al.
Journal of leukocyte biology, 54(6), 590-598 (1993-12-01)
Previously published work has indicated that polyunsaturated fatty acids (PUFA) may enhance neutrophil-mediated damage to host tissues. We have found that endothelial detachment was significantly increased by neutrophils pretreated with docosahexaenoic (22:6, n-3) and arachidonic (20:4, n-6) acids at 10-40
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
R M Senior et al.
The Journal of clinical investigation, 69(2), 384-393 (1982-02-01)
As an approach to facilitating the understanding of proteinases associated with monocytes we have studied U-937 monocytelike cells. Elastase activity was identified in U-937 cell extracts and compared to monocyte elastase activity, neutrophil elastase, and the elastase activity from a
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)
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