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Merck

861650

(+)-Biotin 4-nitrophenyl ester

98%

Synonym(s):

4-Nitrophenyl (+)-biotinate, d-Biotin p-nitrophenyl ester, BNP

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About This Item

Empirical Formula (Hill Notation):
C16H19N3O5S
CAS Number:
33755-53-2
Molecular Weight:
365.40
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
24888552
MDL number:
MFCD15141972
Beilstein/REAXYS Number:
5795805
Assay:
98%
Form:
powder

Key Documents

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InChI key

YUDNXDTXQPYKCA-YDHLFZDLSA-N

SMILES string

[O-][N+](=O)c1ccc(OC(=O)CCCC[C@@H]2SCC3NC(=O)NC23)cc1

InChI

1S/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

assay

98%

form

powder

optical activity

[α]25/D +51°, c = 2 in DMF: AcOH (99:1)

Quality Level

200

solubility

methanol: 25 mg/mL, clear, colorless to greenish-yellow

functional group

ester, nitro, thioether

Related Categories

Application

(+)-Biotin 4-nitrophenyl ester may be used in the preparation of biotin tagged ARC (adenosine-oligoarginine conjugate) derivative during cellular protein uptake studies. It may also be used to prepare biotinylated quinazoline derivatives, which shows inhibitory activities against VEGFR-2 (vascular endothelial growth factor receptor-2) tyrosine kinase. (+)-Biotin 4-nitrophenyl ester undergoes hydrolysis in the presence of Na[17O]H to form [17O2]biotin, which can be used in solid-state 17O NMR spectroscopic experiments to analyze large protein-ligand complexes.

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Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN6446
BCCM3801
BCCG6850
BCCG3893
BCCC5038

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Solomon K Musani et al.
Circulation. Cardiovascular genetics, 8(1), 122-130 (2015-01-07)
Numerous experimental studies suggest that B-type natriuretic peptide (BNP) is cardioprotective; however, in clinical studies, higher plasma BNP concentrations have been associated with incident cardiovascular disease and higher left ventricular mass. Genetic association studies may allow us to determine the
Jing Zong et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 48(1), 75-86 (2018-07-13)
Nuclear localization leucine-rich-repeat protein 1 (NLRP1) is a cytoplasmic protein, involved in autoimmune diseases, mammalian reproduction, neuronal cell death, and stroke. However, the role of NLRP1 in cardiac hypertrophy remains unclear. We used in vivo and in vitro models to
Synthesis of a novel biotin-tagged photoaffinity probe for VEGF receptor tyrosine kinases.
Han SY, et al.
Bioorganic & Medicinal Chemistry Letters, 16(1), 129-133 (2006)
Abhinav Sharma et al.
European journal of heart failure, 19(10), 1310-1320 (2017-06-24)
It is unclear whether distinct pathophysiological processes are present among patients with acute heart failure (AHF), with and without diabetes. Network analysis of biomarkers may identify correlative associations that reflect different pathophysiological pathways. We analysed a panel of 48 circulating
Solid-State 17O NMR Spectroscopy of Large Protein-Ligand Complexes.
Zhu J, et al.
Angewandte Chemie (International Edition in English), 49(45), 8399-8402 (2010)
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