Skip to Content
Merck
All Photos(1)

Key Documents

SML0420

Sigma-Aldrich

TAPI-2 acetate salt

≥98% (HPLC)

Synonym(s):

N-(R)-(2-(Hydroxyaminocarbonyl)methyl)-4-methylpentanoyl-L-t-butyl-glycine-L-alanine 2-aminoethyl amide, Tumor necrosis factor-α protease inhibitor-2, TNF-α protease inhibitor-2

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C19H37N5O5 · xC2H4O2
CAS Number:
Molecular Weight:
415.53 (free base basis)
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Assay

≥98% (HPLC)

form

lyophilized powder

color

white to off-white

shipped in

wet ice

storage temp.

−20°C

SMILES string

CC(O)=O.CC(C)C[C@H](CC(=O)NO)C(=O)N[C@H](C(=O)N[C@@H](C)C(=O)NCCN)C(C)(C)C

InChI

1S/C19H37N5O5.C2H4O2/c1-11(2)9-13(10-14(25)24-29)17(27)23-15(19(4,5)6)18(28)22-12(3)16(26)21-8-7-20;1-2(3)4/h11-13,15,29H,7-10,20H2,1-6H3,(H,21,26)(H,22,28)(H,23,27)(H,24,25);1H3,(H,3,4)/t12-,13+,15+;/m0./s1

InChI key

LMUSZKBIFGOFBD-RAFLFFCLSA-N

Application

TAPI-2 acetate salt has been used to inhibit protease activity in HepG2 cells.

Biochem/physiol Actions

TAPI-2 is a potent inhibitor matrix metalloproteinases and TACE (TNF-α convertase/ADAM17/α-secretase). It blocks the shedding of several cell surface proteins such as β-amyloid precursor protein, inhibits TNF-α release as well as a diverse variety of membrane-anchored cytokines, cell adhesion molecules, receptors, ligands. TAPI-2 is considered a fairly broad metalloproteinase inhibitor, but it much more selective for TACE than GM6001.

Features and Benefits

This compound is featured on the Cytokine Receptors (Tumor Necrosis Receptor Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

High-throughput protease activity cytometry reveals dose-dependent heterogeneity in PMA-mediated ADAM17 activation
Wu L, et al.
Integrative Biology : Quantitative Biosciences from Nano to Macro, 7(5), 513-524 (2015)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service