4-Nitrophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside
Chromogenic substrate for N-acetylglucosaminidase.
4-Nitrophenyl-N-acetyl-?-D-glucosaminide is a chromogenic substrate for N-acetyl-?-glucosaminidase. Hydrolysis of 4-nitrophenyl-N-acetyl-?-D-glucosaminide by N-acetyl-?-glucosaminidase releases 4-nitrophenol, which can be quantified by colorimetric detection at 405 nm as a measure of N-acetyl-?-glucosaminidase activity. It has been used to quantify the activity of N-acetyl-?-D-glucosaminidase in human serum and urine in parenterally fed patients.
4-nitrophenyl N-acetyl-beta-D-glucosaminide is an N-acetyl-beta-D-glucosaminide in which the anomeric hydroxy hydrogen is replaced by a 4-nitrophenyl group. It has a role as a chromogenic compound. It is a C-nitro compound and a N-acetyl-beta-D-glucosaminide. It derives from a 4-nitrophenol.
CAS Number |
3459-18-5 |
Product Name |
4′-Nitrophenyl-2-acetamido-2-deoxy-beta-glucopyranoside |
IUPAC Name |
N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]acetamide |
Molecular Formula |
C14H18N2O8 |
Molecular Weight |
342.3 g/mol |
InChI |
InChI=1S/C14H18N2O8/c1-7(18)15-11-13(20)12(19)10(6-17)24-14(11)23-9-4-2-8(3-5-9)16(21)22/h2-5,10-14,17,19-20H,6H2,1H3,(H,15,18)/t10-,11-,12-,13-,14-/m1/s1 |
InChI Key |
OMRLTNCLYHKQCK-DHGKCCLASA-N |
SMILES |
CC(=O)NC1C(C(C(OC1OC2=CC=C(C=C2)[N+](=O)[O-])CO)O)O |
Synonyms |
4-nitrophenyl N-acetyl-beta-D-glucosaminide, 4-nitrophenyl N-acetylglucosamine, 4-nitrophenyl-2-acetamido-2-deoxy-beta-D-glucopyranoside, 4-nitrophenyl-N-acetyl-2-deoxyglucopyranoside, 4-nitrophenyl-N-acetyl-2-deoxyglucopyranoside, (alpha)-isomer, 4-nitrophenyl-N-acetyl-beta-D-glucopyranoside, 4-nitrophenyl-N-acetylglucosamine, NP-GlcNAc, p-nitrophenyl-N-acetyl-beta-D-glucopyranoside, para-nitrophenyl-N-acetyl-beta-D-glucopyranoside, PNP-GlcNAc, pNPGlcNAc |
Canonical SMILES |
CC(=O)NC1C(C(C(OC1OC2=CC=C(C=C2)[N+](=O)[O-])CO)O)O |
Isomeric SMILES |
CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=CC=C(C=C2)[N+](=O)[O-])CO)O)O |
Items |
Standards |
Results |
Appearance |
White crystal powder |
Complies |
Solubility |
Soluble in DMF, insoluble in ether |
Complies |
Identification |
IR and HPLC |
Complies |
Melting point |
206? ~ 210 ?C |
207? ~209 ? |
Specific rotation
( [?]23/D, c =0.3 inH2O)
|
-18 ~ -20 |
-19.5 |
Any other impurity |
Max. 0.5% |
Complies |
p-Nitrophenol |
Max. 50ppm |
Complies |
Heavy metal |
Max. 20ppm |
Complies |
Residue on ignition |
Max. 0.5% |
0.10% |
TLC |
Should be one spot |
One spot |
Assayby HPLC |
Min. 98% |
99.20% |
CAS No: 3459-18-5
Synonyms: GlcNAc-b-PNP4-Nitrophenyl N-acetyl-b-D-glucosaminePNP-GlcNAc4-Nitrophenyl N-acetyl-b-D-glucosaminide
MDL No: MFCD00063696
Chemical Formula: C14H18N2O8
Molecular Weight: 342.30 |
In Stock.
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References:
1. Muruhn D, Chim. Acta 1976, 73, 453
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