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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:
Molecular Weight:
502.99
Beilstein:
6167019
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
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 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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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 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
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)

Articles

Elastase application index for understanding leukocyte elastase, a 29KDa serine endoprotease.

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