Skip to Content
Merck
All Photos(1)

Key Documents

More Documents

SML1686

Sigma-Aldrich

Neoseptin-3

≥98% (HPLC)

Synonym(s):

(αS)-α-[[4-Amino-3-[2-(4-hydroxyphenyl)ethyl]benzoyl]amino]-benzenebutanoic acid 1,1-dimethylethyl ester

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C29H34N2O4
CAS Number:
1622863-21-1
Molecular Weight:
474.59
UNSPSC Code:
12352200
PubChem Substance ID:
329826015
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D 37 to 45°, c = 0.1 in chloroform

color

white to beige

solubility

DMSO: 15 mg/mL, clear

storage temp.

−20°C

SMILES string

NC1=CC=C(C(N[C@@H](CCC2=CC=CC=C2)C(OC(C)(C)C)=O)=O)C=C1CCC3=CC=C(O)C=C3

Biochem/physiol Actions

Neoseptin-3 is a highly efficacious and specific agonist of the mouse TLR4 (mTLR4)/myeloid differentiation factor 2 (MD-2) complex. Neoseptin-3 binds to MD2, changes the conformation of MD-2 and facilitates active TLR4/MD-2 dimer formation. Neoseptin-3 exhibits no structural similarity to lipid A.
Neoseptin-3 stimulates the activity of mouse TLR4 (mTLR4)/myeloid differentiation factor 2 (mTLR) independently of CD14 (cluster of differentiation 14). This activated mTLR4/ mTLR promotes canonical myeloid differentiation primary response gene 88 (MyD88) and toll-interleukin(IL) 1 receptor (TIR) domain-containing adaptor inducing interferon (IFN)-β (TRIF)-dependent signaling. In addition, neoseptin-3 also stimulates tumor necrosis factor α (TNF-α), IL-6 and IFNβ production in a dose-dependent manner.

Hazard Statements

H413

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 4

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

Ying Wang et al.
Proceedings of the National Academy of Sciences of the United States of America, 113(7), E884-E893 (2016-02-03)
Structurally disparate molecules reportedly engage and activate Toll-like receptor (TLR) 4 and other TLRs, yet the interactions that mediate binding and activation by dissimilar ligands remain unknown. We describe Neoseptins, chemically synthesized peptidomimetics that bear no structural similarity to the

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