33755-53-2

Basic information

• Product Name: D-BIOTIN P-NITROPHENYL ESTER
• Synonyms: PBNP;4-NITROPHENYL (+)-BIOTINATE;(+)-BIOTIN 4-NITROPHENYL ESTER;BIOTIN P-NITROPHENYL ESTER;BIOTIN-ONP;BNP;D-BIOTIN P-NITROPHENYL ESTER;biotinyl-4-nitrophenyl ester
• CAS NO: 33755-53-2
• Molecular Formula: C₁₆H₁₉N₃O₅S
• Molecular Weight: 365.4
• EINECS: 1533716-785-6
• Product Categories: cytokine
• Mol File: 33755-53-2.mol

Chemical Properties

• Melting Point: 163-165 °C(lit.)
• Boiling Point: 642.9 °C at 760 mmHg
• Flash Point: 342.6 °C
• Appearance: /
• Density: 1.326 g/cm³
• Vapor Pressure: 2.03E-16mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: −20°C
• Solubility: methanol: soluble25mg/mL, clear, colorless to greenish-yellow
• PKA: 13.89±0.40(Predicted)
• BRN: 5795805
• CAS DataBase Reference: D-BIOTIN P-NITROPHENYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: D-BIOTIN P-NITROPHENYL ESTER(33755-53-2)
• EPA Substance Registry System: D-BIOTIN P-NITROPHENYL ESTER(33755-53-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 33755-53-2(Hazardous Substances Data)

Usage

Uses

1. Used in Cellular Protein Uptake Studies:
D-BIOTIN P-NITROPHENYL ESTER is used as a reagent for the preparation of biotin tagged ARC (adenosine-oligoarginine conjugate) derivatives. This application is crucial in cellular protein uptake studies, aiding researchers in understanding the mechanisms of protein transport within cells.
2. Used in the Synthesis of Biotinylated Quinazoline Derivatives:
In the field of medicinal chemistry, D-BIOTIN P-NITROPHENYL ESTER is utilized to prepare biotinylated quinazoline derivatives. These derivatives have demonstrated inhibitory activities against VEGFR-2 (vascular endothelial growth factor receptor-2) tyrosine kinase, making them potential candidates for cancer research and therapeutic development.
3. Used in Solid-State 17O NMR Spectroscopy:
D-BIOTIN P-NITROPHENYL ESTER undergoes hydrolysis in the presence of Na[17O]H to form [17O2]biotin. This reaction is essential for its use in solid-state 17O NMR spectroscopic experiments, which are employed to analyze large protein-ligand complexes. This application is vital for structural biology and the study of protein-ligand interactions at the molecular level.
4. Used in Research and Diagnostics:
Although D-BIOTIN P-NITROPHENYL ESTER is intended for research use only and not for diagnostic procedures, it has been employed in the development of the Brain natriuretic peptide EIA Kit. This kit is used to measure brain natriuretic peptide (BNP) secreted in human neonatal ventricular cardiomyocyte culture, providing valuable insights into cardiac function and related conditions.

Biochem/physiol Actions

Brain natriuretic peptide (BNP) expressed in mammalian brain and atrial natriuretic peptide (ANP) facilitates various physiological functions including regulation of blood pressure and cardiac remodeling. BNP acts as a potential biomarker of high left ventricular end-diastolic pressure in patients with symptomatic left ventricular (LV) dysfunction. Elevated expression of BNP is observed in acute myocardial infarction (AMI) patients. BNP is also implicated in several biological functions such as diuresis, natriureis, hypotensive action and inhibition of aldosterone secretion.

Purification Methods

The ester has been recrystallised by dissolving 2g in 95% EtOH (30mL), heated to dissolve, then cooled in an ice-water bath. The crystals are collected, washed with ice-cold 95% EtOH (5mL) and dried over P2O5. The RF on silica plates (CHCl3/MeOH 19:1) is 0.19 [Bodanszky & Fagan J Am Chem Soc 99 235 1977].

InChI:InChI=1/C16H19N3O5S/c20-14(24-11-7-5-10(6-8-11)19(22)23)4-2-1-3-13-15-12(9-25-13)17-16(21)18-15/h5-8,12-13,15H,1-4,9H2,(H2,17,18,21)/t12-,13-,15-/m0/s1

Upstream product

• 62062-42-4 5-((3aS)-2-oxo-1-trifluoroacetyl-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid 4-nitro-phenyl ester 
• 58-85-5 biotin 
• 100-02-7 4-nitro-phenol 
• 658-78-6 1-nitro-4-trifluoroacetoxy-benzene 

Downstream Products

• 62062-43-5 Boc-Lys(biotinyl)-OH 
• 120447-60-1 biotinylglycylglycine 
• 106451-92-7 6-N-Biotinylaminohexanol 
• 239115-57-2 (S)-3-(4-Hydroxy-phenyl)-2-{10-[2-(2-{2-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-ethoxy}-ethoxy)-ethoxy]-decanoylamino}-propionic acid methyl ester 
• 239115-66-3 N-10-<2-(2-<2-(biotinylamino)ethoxy>ethoxy)ethoxy>decanoyl-(L)-(3,5-diiodo)tyrosine methyl ester 
• 289714-02-9 5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]-N-[2-[2-(2-hydroxyethoxy)ethoxy]ethyl]pentanamide 
• 224583-35-1 6-N-Biotinylaminohexyl hydrogenphosphonate 
• 224583-37-3 6-N-Biotinylaminohexyl isopropyl hydrogenphosphonate 
• 576-19-2 biocytin 
• 875770-34-6 N-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl]biotinamide 
• 65953-56-2 N-(6-aminohexyl)-5-((3aS,4S,6aR)-3a,6a-dimethyl-2-oxohexahydro-1H-thieno[3,4-d] imidazol-4-yl)pentanamide 
• 126837-84-1 N-(2,2-dimethoxyethyl)biotinamide 

Relevant articles and documents

Targeted Diazotransfer Reagents Enable Selective Modification of Proteins with Azides

In chemical biology, azides are used to chemically manipulate target structures in a bioorthogonal manner for a plethora of applications ranging from target identification to the synthesis of homogeneously modified protein conjugates. While a variety of methods have been established to introduce the azido group into recombinant proteins, a method that directly converts specific amino groups in endogenous proteins is lacking. Here, we report the first biotin-tethered diazotransfer reagent DtBio and demonstrate that it selectively modifies the model proteins streptavidin and avidin and the membrane protein BioY on cell surface. The reagent converts amines in the proximity of the binding pocket to azides and leaves the remaining amino groups in streptavidin untouched. Reagents of this novel class will find use in target identification as well as the selective functionalization and bioorthogonal protection of proteins.