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3150-24-1,MFCD00150725
Catalog No.:AA00I5VX

3150-24-1 | 4-Nitrophenyl-beta-d-galactopyranoside

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1g
98% HPLC
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00I5VX
Chemical Name:
4-Nitrophenyl-beta-d-galactopyranoside
CAS Number:
3150-24-1
Molecular Formula:
C12H15NO8
Molecular Weight:
301.2494
MDL Number:
MFCD00150725
SMILES:
OC[C@H]1O[C@@H](Oc2ccc(cc2)[N+](=O)[O-])[C@@H]([C@H]([C@H]1O)O)O
Properties
Computed Properties
 
Complexity:
354  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
3  
XLogP3:
-0.4  

Downstream Synthesis Route
4-nitrophenyl2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
  3150-24-1 

[1]CurrentPatentAssignee:UNIVERSITYOFDUBLIN-US2014/256924,2014,A1Locationinpatent:Paragraph0200;0202-0203

[2]Aizawa[Enzymology,1939,vol.6,p.321,323]

[3]Locationinpatent:experimentalpartGubica,Tomasz;Temeriusz,Andrzej;Paradowska,Katarzyna;Ostrowski,Andrzej;Klimentowska,Paulina;Cyranski,MichalK.[CarbohydrateResearch,2009,vol.344,#13,p.1734-1744]

[4]Wei,Jinhua;Lv,Xun;Lue,Yang;Yang,Gangzhu;Fu,Lifeng;Yang,Liu;Wang,Jianjun;Gao,Jianhui;Cheng,Shuihong;Duan,Qian;Jin,Cheng;Li,Xuebing[EuropeanJournalofOrganicChemistry,2013,#12,p.2414-2419]

[5]Joachim,Ines;Rikker,Sebastian;Hauck,Dirk;Ponader,Daniela;Boden,Sophia;Sommer,Roman;Hartmann,Laura;Titz,Alexander[OrganicandBiomolecularChemistry,2016,vol.14,#33,p.7933-7948]

[1]BulletinoftheChemicalSocietyofJapan,2000,vol.73,p.2553-2558

[2]JournalofOrganicChemistry,2020,vol.85,p.16236-16242

[3]EuropeanJournalofOrganicChemistry,2021,vol.2021,p.3812-3818

[4]JournalofExperimentalMedicine,1929,vol.50,p.521,528

[5]Carbohydrateresearch,1981,vol.89,p.211-220

[6]Tetrahedron,1998,vol.54,p.4051-4065

[7]Chemistry-AEuropeanJournal,2005,vol.11,p.5538-5544

[8]Chemistry-AEuropeanJournal,2002,vol.8,p.2684-2690

[9]Patent:US6656917,2003,B1.Locationinpatent:Pagecolumn32

[10]BioorganicandMedicinalChemistryLetters,2010,vol.20,p.315-317

[11]BioconjugateChemistry,2010,vol.21,p.2119-2127

[12]Patent:US2014/256924,2014,A1.Locationinpatent:Paragraph0200;0203-0204

[1]Wong,Chi-Huey;Ichikawa,Yoshitaka;Krach,Thomas;Narvor,ChristineGautheron-Le;Dumas,DavidP.;Look,GaryC.[JournaloftheAmericanChemicalSociety,1991,vol.113,#21,p.8137-8145]

[2]Wong,Chi-Huey;Krach,Thomas;Narvor,ChristineGautheron-Le;Ichikawa,Yoshitaka;Look,GaryC.;etal.[TetrahedronLetters,1991,vol.32,#37,p.4867-4870]

N-Acetyl-D-glucosamine 
  3150-24-1   
N-acetyl-D-lactosamine 

[1]Tran,ChuongHao;Critchley,Peter;Crout,DavidH.G.;Britten,ChristopherJ.;Witham,SaraJ.;Bird,MichaelI.[JournaloftheChemicalSociety.PerkintransactionsI,1998,#15,p.2295-2299]

[2]Finch,Paul;Yoon,JungHae[CarbohydrateResearch,1997,vol.303,#3,p.339-345]

[3]Giordano,Assunta;Tramice,Annabella;Andreotti,Giuseppina;Mollo,Ernesto;Trincone,Antonio[BioorganicandMedicinalChemistryLetters,2005,vol.15,#1,p.139-143]

[4]Ajisaka,Katsumi;Fujimoto,Hiroshi;Isomura,Megumi[CarbohydrateResearch,1994,vol.259,#1,p.103-116]

[5]Vetere,Amedeo;Novelli,Lara;Paoletti,Sergio[JournalofCarbohydrateChemistry,1999,vol.18,#5,p.515-521]

[6]Sandoval,Manuel;Civera,Concepción;Berenguer,José;García-Blanco,Francisco;Hernaiz,MaríaJ.[Tetrahedron,2013,vol.69,#3,p.1148-1152]

[1]Cipolla,Laura;Lotti,Marina;DeGioia,Luca;Nicotra,Francesco[JournalofCarbohydrateChemistry,2003,vol.22,#7-8,p.631-644]

[2]CurrentPatentAssignee:BAYERAG-US6271342,2001,B1

[3]Ekborg,Goeran;Vranesic,Branka;Bhattacharjee,ApurbaK.;Kovacs,Pavol;Glaudemans,CornelisP.J.[CarbohydrateResearch,1985,vol.142,p.203-212]

Literature

Title: Efficient and regioselective synthesis of globotriose by a novel α-galactosidase from Bacteroides fragilis.

Journal: Applied microbiology and biotechnology 20160801

Title: Novel fluorescent biosensor for α-glucosidase inhibitor screening based on cationic conjugated polymers.

Journal: ACS applied materials & interfaces 20120801

Title: New development in in-capillary electrophoresis techniques for kinetic and inhibition study of enzymes.

Journal: Analytica chimica acta 20120413

Title: Ser-796 of β-galactosidase (Escherichia coli) plays a key role in maintaining a balance between the opened and closed conformations of the catalytically important active site loop.

Journal: Archives of biochemistry and biophysics 20120115

Title: A glycopeptide dendrimer inhibitor of the galactose-specific lectin LecA and of Pseudomonas aeruginosa biofilms.

Journal: Angewandte Chemie (International ed. in English) 20111104

Title: Evaluation of polyhydroxybenzophenones as α-glucosidase inhibitors.

Journal: Archiv der Pharmazie 20110201

Title: Extraction, partial characterization, and storage stability of β-glucosidase from propolis.

Journal: Journal of food science 20110101

Title: Tunicamycin inhibition of N-glycosylation of α-glucosidase from Aspergillus niveus: partial influence on biochemical properties.

Journal: Biotechnology letters 20101001

Title: Heterologous expression of glycoside hydrolase family 2 and 42 β-galactosidases of lactic acid bacteria in Lactococcus lactis.

Journal: Systematic and applied microbiology 20101001

Title: Aspergillus nidulans alpha-galactosidase of glycoside hydrolase family 36 catalyses the formation of alpha-galacto-oligosaccharides by transglycosylation.

Journal: The FEBS journal 20100901

Title: Characterization of the interdependency between residues that bind the substrate in a beta-glycosidase.

Journal: Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas 20100101

Title: Characterization of glycosyl hydrolase family 3 beta-N-acetylglucosaminidases from Thermotoga maritima and Thermotoga neapolitana.

Journal: Journal of bioscience and bioengineering 20091201

Title: A new beta-galactosidase with a low temperature optimum isolated from the Antarctic Arthrobacter sp. 20B: gene cloning, purification and characterization.

Journal: Archives of microbiology 20091101

Title: Use of quorum sensing antagonists to deter the formation of crystalline Proteus mirabilis biofilms.

Journal: International journal of antimicrobial agents 20091001

Title: Crystal structure of alpha-1,3-galactosyltransferase (alpha3GT) in a complex with p-nitrophenyl-beta-galactoside (pNPbetaGal).

Journal: Biochemical and biophysical research communications 20090807

Title: Practical considerations when using temperature to obtain rate constants and activation thermodynamics of enzymes with two catalytic steps: native and N460T-beta-galactosidase (E. coli) as examples.

Journal: The protein journal 20090201

Title: Cloning and characterization of a novel alpha-galactosidase from Bifidobacterium breve 203 capable of synthesizing Gal-alpha-1,4 linkage.

Journal: FEMS microbiology letters 20080801

Title: The cost of expression of Escherichia coli lac operon proteins is in the process, not in the products.

Journal: Genetics 20080301

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

Journal: The Journal of biological chemistry 20071130

Title: Purification and properties of alpha-galactosidase from white-rot fungus Pleurotus florida.

Journal: Indian journal of biochemistry & biophysics 20070401

Title: Reduction of flatus-inducing factors in soymilk by immobilized alpha-galactosidase.

Journal: Biotechnology and applied biochemistry 20060901

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

Journal: Environmental microbiology 20060601

Title: Characterisation of an alpha-galactosidase with potential relevance to ripening related texture changes.

Journal: Phytochemistry 20060201

Title: Comparison of polymerase chain reaction-restriction fragment length polymorphism assay and enzyme assay for diagnosis of G(M1)-gangliosidosis in Shiba dogs.

Journal: Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc 20040701

Title: Properties of a recombinant beta-glucosidase from polycentric anaerobic fungus Orpinomyces PC-2 and its application for cellulose hydrolysis.

Journal: Applied biochemistry and biotechnology 20040101

Title: Expression, isolation, purification, and biochemical properties of trehalose-6-phosphate hydrolase from thermoresistant strain Bacillus sp. GP16.

Journal: Biochemistry. Biokhimiia 20030901

Title: Preparation and properties of alpha-galactosidase chemically attached to activated chitin.

Journal: Artificial cells, blood substitutes, and immobilization biotechnology 20030801

Title: Aromatic stacking in the sugar binding site of the lactose permease.

Journal: Biochemistry 20030218

Title: Trp-999 of beta-galactosidase (Escherichia coli) is a key residue for binding, catalysis, and synthesis of allolactose, the natural lac operon inducer.

Journal: Biochemistry 20030218

Title: Characterization of a beta-glycosidase highly active on disaccharides and of a beta-galactosidase from Tenebrio molitor midgut lumen.

Journal: Insect biochemistry and molecular biology 20030201

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

Journal: Biochemistry 20021029

Title: Rapid detection of lytic antimicrobial activity against yeast and filamentous fungi.

Journal: Journal of microbiological methods 20020301

Title: Insights into the functional architecture of the catalytic center of a maize beta-glucosidase Zm-p60.1.

Journal: Plant physiology 20011101

Title: Purification and characterization of isoforms of beta-galactosidases in mung bean seedlings.

Journal: Phytochemistry 20010601

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Tags:3150-24-1 Molecular Formula|3150-24-1 MDL|3150-24-1 SMILES|3150-24-1 4-Nitrophenyl-beta-d-galactopyranoside