3459-18-5, 4-Nitrophenyl-2-acetamido-2-deoxy-β-D-glucopyranoside, CAS: 3459-18-5

PNP-GlcNAc, 4-Nitrophenyl-2-acetamido-2-deoxy-β-D-glucopyranoside, CAS: 3459-18-5
C14H18N2O8 / 342.30
MFCD00063696

4-Nitrophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside

Chromogenic substrate for N-acetylglucosaminidase.

4-Nitrophenyl-N-acetyl-β-D-glucosaminide is a chromogenic substrate for N-acetyl-β-glucosaminidase. Hydrolysis of 4-nitrophenyl-N-acetyl-β-D-glucosaminide by N-acetyl-β-glucosaminidase releases 4-nitrophenol, which can be quantified by colorimetric detection at 405 nm as a measure of N-acetyl-β-glucosaminidase activity. It has been used to quantify the activity of N-acetyl-β-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 ( [α]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

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References:

1. Muruhn D, Chim. Acta 1976, 73, 453

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