Page last updated: 2024-12-07

4-nitrophenyl-2-acetamido-2-deoxy-beta-d-glucopyranoside

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

4-nitrophenyl-2-acetamido-2-deoxy-beta-d-glucopyranoside is a synthetic glycoside that serves as a substrate for various glycosidases, including lysozyme. It is commonly used in studies investigating the mechanism of action of glycosidases and as a model substrate for studying the catalytic properties of these enzymes. The compound is typically synthesized through a series of reactions starting with D-glucosamine and involving protection, acetylation, and coupling with 4-nitrophenol. 4-nitrophenyl-2-acetamido-2-deoxy-beta-d-glucopyranoside's importance lies in its ability to mimic the natural substrates of glycosidases, allowing for detailed analysis of enzyme activity and substrate specificity. Studies involving this compound contribute to our understanding of glycosidase function, which is crucial for various biological processes, including carbohydrate metabolism, immune response, and bacterial cell wall degradation.'
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4-nitrophenyl-N-acetyl-2-deoxyglucopyranoside: RN given refers to (beta)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

4-nitrophenyl N-acetyl-beta-D-glucosaminide : An N-acetyl-beta-D-glucosaminide in which the anomeric hydroxy hydrogen is replaced by a 4-nitrophenyl group. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID102416
CHEMBL ID595014
CHEBI ID90343
SCHEMBL ID262925
MeSH IDM0062406

Synonyms (60)

Synonym
4-nitrophenyl 2-acetamido-2-deoxy-|a-d-glucopyranoside
AKOS002688252
SMP1_000214
4-nitrophenyl n-acetyl-beta-d-glucosaminide, >=99% (tlc)
4-nitrophenyl-n-acetyl-beta-d-glucosaminide
LEC ,
3459-18-5
CHEMBL595014
chebi:90343 ,
4-nitrophenyl 2-acetamido-2-deoxy-beta-d-glucopyranoside
n-[(2s,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]acetamide
4-nitrophenyl n-acetyl-beta-d-glucosaminide
4-nitrophenyl-2-acetamido-2-deoxy-beta-d-glucopyranoside
4-nitrophenyl-n-acetyl-2-deoxyglucopyranoside
4'-nitrophenyl-2-acetamido-2-deoxy-beta-glucopyranoside
unii-gvy9aa7y5c
gvy9aa7y5c ,
einecs 222-398-7
AKOS016015692
glcnac1-b-pnp
p-nitrophenyl 2-acetamido-2-deoxy-beta-d-glucopyranoside
SCHEMBL262925
mfcd00063696
p-nitrophenyl-beta-d-n-acetyl-glucosaminide
.beta.-d-glucopyranoside, 4-nitrophenyl 2-(acetylamino)-2-deoxy-
p-nitrophenyl-n-acetyl-.beta.-d-glucosaminide
p-nitrophenyl-2-acetamido-2-deoxy-.beta.-d-glucopyranoside
OMRLTNCLYHKQCK-DHGKCCLASA-N
4-nitrophenyl 2-(acetylamino)-2-deoxyhexopyranoside #
4-nitrophenyl-n-acetyl-.beta.-.delta.-glucosaminide
p-nitrophenyl-2-acetamido-2-deoxy-.alpha.-d-glucopyranoside
4-nitrophenyl 2-acetamido-2-deoxy-beta-d-glucoside
p-nitrophenyl 2-acetamido-2-deoxy-beta-d-glucoside
p-nitrophenyl n-acetyl-beta-d-glucosaminide
AC-33214
4-nitrophenyl n-acetyl-i(2)-d-glucosaminide
Z1801318714
AS-70776
4-nitrophenyl 2-acetamido-2-deoxy-betad-glucopyranoside
4-nitrophenyl 2-(acetylamino)-2-deoxy-beta-d-glucopyranoside
Q27162478
n-[(2s,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)tetrahydropyran-3-yl]acetamide
|a-d-glucopyranoside, 4-nitrophenyl2-(acetylamino)-2-deoxy-
n-((2s,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)tetrahydro-2h-pyran-3-yl)acetamide
AMY41705
p-nitrophenyl-2-acetamido-2-deoxy-beta-d-glucopyranoside pnp-beta-d-glcnac
4-nitrophenyl-n-acetyl- beta - d-glucosaminide
b-d-glucopyranoside, 4-nitrophenyl 2-(acetylamino)-2-deoxy-
avr-48
n-((2s,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)tetrahydro-2h-pyran-3-yl) acetamide
A874930
p-nitrophenyl 2-acetamido-2-deoxy-?-d-glucopyranoside
4-nitrophenyl2-acetamido-2-deoxy-beta-d-glucopyranoside
HY-W011183
4-nitrophenyl-n-acetyl-|a-d-glucosaminide
CS-W011899
DTXSID301275049
AKOS040755912
EX-A7998K
PD124689
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
chromogenic compoundColourless, endogenous or exogenous pigment precursors that may be transformed by biological mechanisms into coloured compounds. They are used in biochemical assays and in diagnosis as indicators, particularly in the form of enzyme substrates.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
C-nitro compoundA nitro compound having the nitro group (-NO2) attached to a carbon atom.
N-acetyl-beta-D-glucosaminideAny N-acetyl-D-glucosaminide having beta-configuration at the anomeric centre.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID1872820Inhibition of TLR4 expression in human monocytes2022European journal of medicinal chemistry, May-05, Volume: 235Toll-like receptor 4 (TLR4) inhibitors: Current research and prospective.
AID450447Activity of Escherichia coli O55:H7 glycosyltransferase WbgO relative to GlcNAc2009Bioorganic & medicinal chemistry, Jul-15, Volume: 17, Issue:14
Characterization and synthetic application of a novel beta1,3-galactosyltransferase from Escherichia coli O55:H7.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (26)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (3.85)18.7374
1990's9 (34.62)18.2507
2000's11 (42.31)29.6817
2010's4 (15.38)24.3611
2020's1 (3.85)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.02

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.02 (24.57)
Research Supply Index3.33 (2.92)
Research Growth Index5.35 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.02)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (3.70%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other26 (96.30%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]