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861650

Sigma-Aldrich

(+)-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
Beilstein:
5795805
MDL number:
MFCD15141972
UNSPSC Code:
12352108
PubChem Substance ID:
24888552
NACRES:
NA.22

Assay

98%

form

powder

optical activity

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

mp

163-165 °C (lit.)

solubility

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

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

InChI key

YUDNXDTXQPYKCA-YDHLFZDLSA-N

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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.

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Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Jingui Xue et al.
Journal of alternative and complementary medicine (New York, N.Y.), 25(8), 856-860 (2019-07-12)
Objectives: Chronic heart failure (CHF) is a chronic and progressive disease with high incidence. The aim of this study
Björn Redfors et al.
Circulation (2018-04-19)
Background -Elevated B-type natriuretic peptide (BNP) is reflective of impaired cardiac function and is associated with worse prognosis among
Identification of the ability of highly charged nanomolar inhibitors of protein kinases to cross plasma membranes and carry a protein into cells.
Uri A, et al.
Bioorganic & Medicinal Chemistry Letters, 12(16), 2117-2120 (2002)
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Changes in echocardiographic parameters and biomarkers of cardiac and venous pressures or estimated plasma volume during hospitalization associated with decongestive treatments in acute heart failure (AHF) patients with either preserved left ventricular ejection fraction (LVEF) (HFPEF) or reduced LVEF (HFREF)
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