35599-02-1 Usage
Description
4-NITROPHENYL-BETA-D-MANNOPYRANOSIDE, also known as p-Nitrophenyl β-D-Mannopyranoside, is a synthetic compound with the chemical formula C12H15NO8. It is a chromogenic substrate commonly used in biochemical research and organic synthesis. Its structure consists of a β-D-mannopyranose sugar moiety linked to a 4-nitrophenyl aglycone, which upon enzymatic cleavage, releases a yellow-colored 4-nitrophenol product. This property makes it a useful tool for monitoring enzymatic activity and studying enzyme kinetics.
Uses
Used in Biochemical Research:
4-NITROPHENYL-BETA-D-MANNOPYRANOSIDE is used as a substrate to analyze the action mechanism of various glycosidase enzymes and determine their kinetic parameters through techniques such as isothermal titration calorimetry (ITC). This allows researchers to gain insights into the enzyme's catalytic properties and its interactions with substrates.
Used in Enzyme Assays:
4-NITROPHENYL-BETA-D-MANNOPYRANOSIDE is used as a substrate for enzyme assays, specifically for glycosidase enzymes such as GH1-glucosidase (EaBgl1A). The enzymatic hydrolysis of this substrate results in the release of 4-nitrophenol, which can be easily quantified by measuring the absorbance at 400 nm. This provides a convenient and sensitive method for assessing enzyme activity and inhibition.
Used in Enzyme Screening:
4-NITROPHENYL-BETA-D-MANNOPYRANOSIDE is used as a substrate for screening enzymes from various sources, such as cucumber enzymes. This allows researchers to identify and characterize novel enzymes with potential applications in research, industry, or therapeutics.
Used in Organic Synthesis:
4-NITROPHENYL-BETA-D-MANNOPYRANOSIDE is also used in organic synthesis as a building block or intermediate for the preparation of various complex carbohydrates, glycoconjugates, and other bioactive molecules. Its unique structure and reactivity make it a valuable compound in the synthesis of pharmaceuticals, diagnostics, and other specialty chemicals.
Biochem/physiol Actions
4-Nitrophenyl β-D-mannopyranoside or p-Nitrophenyl-β-D-mannopyranoside is a substrate for determining the activity of β-D-mannopyranosidase, an enzyme required to study about glycoproteins structural details.
Check Digit Verification of cas no
The CAS Registry Mumber 35599-02-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,5,5,9 and 9 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 35599-02:
(7*3)+(6*5)+(5*5)+(4*9)+(3*9)+(2*0)+(1*2)=141
141 % 10 = 1
So 35599-02-1 is a valid CAS Registry Number.
InChI:InChI=1/C12H15NO8/c14-5-8-9(15)10(16)11(17)12(21-8)20-7-3-1-6(2-4-7)13(18)19/h1-4,8-12,14-17H,5H2/t8-,9-,10+,11+,12-/m1/s1
35599-02-1Relevant articles and documents
Garegg et al.
, p. 313 (1979)
Glycosynthase with broad substrate specificity-an efficient biocatalyst for the construction of oligosaccharide library
Wei, Jinhua,Lv, Xun,Lue, Yang,Yang, Gangzhu,Fu, Lifeng,Yang, Liu,Wang, Jianjun,Gao, Jianhui,Cheng, Shuihong,Duan, Qian,Jin, Cheng,Li, Xuebing
supporting information, p. 2414 - 2419 (2013/05/23)
A versatile glycosynthase (TnG-E338A) with strikingly broad substrate scope has been developed from Thermus nonproteolyticus β-glycosidase (TnG) by using site-directed mutagenesis. The practical utility of this biocatalyst has been demonstrated by the facile generation of a small library containing various oligosaccharides and a steroidal glycoside (total 25 compounds) in up to 100 % isolated yield. Moreover, an array of eight gluco-oligosaccharides has been readily synthesized by the enzyme in a one-pot, parallel reaction, which highlights its potential in the combinatorial construction of a carbohydrate library that will assist glycomic and glycotherapeutic research. Significantly, the enzyme provides a means by which glycosynthase technology may be extended to combinatorial chemistry.
Carbohydrate-carbohydrate interactions in water with glycophanes as model systems
Morales, Juan Carlos,Zurita, Dacil,Penades, Soledad
, p. 9212 - 9222 (2007/10/03)
The synthesis and conformational properties of glycophanes 2 and 3 (cyclodextrin-cyclophane hybrid receptors containing two maltose units linked by (4-hydroxymethyl) benzoic acid spacer) are described. The binding properties in water of these receptors with a series of 4-nitrophenyl glycosides with α- and β-configurations at the anomeric center have been studied using 1H NMR spectroscopy and molecular mechanics calculations. A comparison of these properties with those of glycophane 1 (an α,α-trehalose containing glycophane) and α-cyclodextrin (αCD) using the same glycosides shows the existence of a stabilizing contribution to the free energy of binding in the case of of glycophanes but not in the case of the αCD system. This contribution is due to carbohydrate-carbohydrate interactions between both host and guest lipophilic sugar surfaces. Glycophanes 1, 2, and 3 show similar α/β selectivity on binding the ligands, despite the great flexibility of 3 related to 1 and 2. Parallels are drawn between the thermodynamic behavior of these model systems and that proposed for sugar- protein interactions.
SYNTHESIS OF 4-NITROPHENYL 2,3,6-TRI-O-ACETYL-4-DEOXY-β-D-LYXO-HEXOPYRANOSIDE AND A NEW SYNTHESIS OF 4-NITROPHENYL β-D-MANNOPYRANOSIDE
Baggett, Neil,Marsden, Brian J.
, p. 285 - 291 (2007/10/02)
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