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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

Quality Level

200

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

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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Synthesis of a novel biotin-tagged photoaffinity probe for VEGF receptor tyrosine kinases.
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Bioorganic & Medicinal Chemistry Letters, 16(1), 129-133 (2006)
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American journal of physiology. Renal physiology, 317(2), F275-F285 (2019-05-23)
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