4-Nitrophenyl α-D-galactopyranoside

Names

[ Name ]:
4-Nitrophenyl α-D-galactopyranoside

[Synonym ]:
4-nitrophenyl-alpha-D-galactoside
4-Nitrophenyl β-D-galactopyranoside
1-O-[P-NITROPHENYL]-β-D-GALACTOPYRANOSE
β-D-Galactopyranoside, 4-nitrophenyl (9CI)
β-D-Galactopyranoside, 4-nitrophenyl
MFCD00065050
p-Nitrophenyl .α.-D-galactopyranoside
α-D-Galactopyranoside, 4-nitrophenyl
p-Nitrophenyl α-D-galactopyranoside
4-Nitrophenyl α-D-galactopyranoside
EINECS 231-343-6
p-Nitrophenyl β-D-galactopyranoside
4-Nitrophenyl a-D-galactopyranoside

Biological Activity

[Description]:

4-Nitrophenyl α-D-galactopyranoside (PNP-alpha-D-Gal) is an artificial substrate of 4-nitrophenyl (pNP) glycopyranoside for detecting α-galactosidase activity. The amount of released pNP is significantly increased when 4-Nitrophenyl α-D-galactopyranoside is used as substrates[1].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[In Vitro]

Using 4-nitorophenol (pNP)-glycopyranosides as pseudosubstrates, the amount of liberated pNP from the 4-Nitrophenyl α-D-galactopyranoside is significantly higher than that from the other pNP-glycopyranosides at pH 4.0 whereas no activity was detected at pH 7.0[1]. The digestion assays using 4-nitrophenyl (pNP) glycopyranosides as artificial substrates shows that yieldin liberated galactose residues from 4-Nitrophenyl α-D-galactopyranoside mainly at pH 4.0, i.e. the pH level where yield threshold is decreased at most[1].

[References]

[1]. Okamoto-Nakazato A. Implications of the galactosidase activity of yieldin in the regulatory mechanism of yield threshold that is fundamental to cell wall extension. Physiol Plant. 2018 Jun;163(2):259-266.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
582.2±50.0 °C at 760 mmHg

[ Melting Point ]:
166-169ºC

[ Molecular Formula ]:
C₁₂H₁₅NO₈

[ Molecular Weight ]:
301.249

[ Flash Point ]:
305.9±30.1 °C

[ Exact Mass ]:
301.079773

[ PSA ]:
145.20000

[ LogP ]:
-0.55

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.648

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

The galactophilic lectin, LecA, contributes to biofilm development in Pseudomonas aeruginosa.

Environ. Microbiol. 8(6) , 1095-104, (2006)

LecA (PA-IL) is a cytotoxic lectin and adhesin produced by Pseudomonas aeruginosa which binds hydrophobic galactosides with high specificity and affinity. By using a lecA-egfp translation fusion and i...

Cryptosporidium p30, a galactose/N-acetylgalactosamine-specific lectin, mediates infection in vitro.

J. Biol. Chem. 282 , 34877-87, (2007)

Cryptosporidium sp. cause human and animal diarrheal disease worldwide. The molecular mechanisms underlying Cryptosporidium attachment to, and invasion of, host cells are poorly understood. Previously...

Binding of hydrophobic D-galactopyranosides to the lactose permease of Escherichia coli.

Biochemistry 41(43) , 13039-45, (2002)

Binding of alpha- and beta-D-galactopyranosides with different hydrophobic aglycons was compared using substrate protection against N-ethylmaleimide alkylation of single-Cys148 lactose permease. As de...