(+)-Biotin 4-nitrophenyl ester

Name: (+)-Biotin 4-nitrophenyl ester
Brand: ALDRICH
Price: 112 USD

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

Key Documents

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Product Name

(+)-Biotin 4-nitrophenyl ester, 98%

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)

mp

163-165 °C (lit.)

solubility

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

functional group

ester
nitro
thioether

Quality Level

200

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Show Differences

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This Item	H1759	1048	N1268
Sigma-Aldrich 861650 (+)-Biotin 4-nitrophenyl ester	Sigma-Aldrich H1759 (+)-Biotin N-hydroxysuccinimide ester	Sigma-Aldrich 1048 4-Nitrophenol	Sigma-Aldrich N1268 4-Nitrophenyl β-D-mannopyranoside
assay 98%	assay ≥98% (HPLC)	assay -	assay ≥98%
solubility methanol: 25 mg/mL, clear, colorless to greenish-yellow	solubility DMF: ≤50 mg/mL (Stable for at least one month in dry DMF), DMSO: soluble	solubility ethanol: 95%, clear, dark yellow (100 mg/mL)	solubility water: 10 mg/mL, clear, colorless to very faintly green
Quality Level 200	Quality Level 200	Quality Level 200	Quality Level 200
mp 163-165 °C (lit.)	mp 212 °C	mp 110-115 °C (lit.)	mp -
form powder	form powder	form powder	form powder
optical activity [α]25/D +51°, c = 2 in DMF: AcOH (99:1)	optical activity -	optical activity -	optical activity -

Application

(+)-Biotin 4-nitrophenyl ester may be used in the preparation of biotin tagged ARC (adenosine-oligoarginine conjugate) derivative during cellular protein uptake studies.[1] 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.[2] (+)-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.[3]

Automate your Biotin tagging with Synple Automated Synthesis Platform (SYNPLE-SC002)

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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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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B-Type Natriuretic Peptide Assessment in Patients Undergoing Revascularization for Left Main Coronary Artery Disease: Analysis from the EXCEL Trial.

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

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)

The Efficacy and Safety of Xinmailong Injection in Patients with Chronic Heart Failure: A Multicenter Randomized Double-Blind Placebo-Controlled Trial.

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

Reduced endothelial nitric oxide synthase activation contributes to cardiovascular injury during chronic kidney disease progression.

Isabel Amador-Martínez et al.

American journal of physiology. Renal physiology, 317(2), F275-F285 (2019-05-23)

Major cardiovascular events are a common complication in patients with chronic kidney disease (CKD). Endothelial dysfunction can contribute to the cardiovascular injury observed in CKD. Here, we used a rat model of acute kidney injury to CKD transition to investigate

Point-of-Care Ultrasound Abnormalities in Late-Onset Severe Preeclampsia: Prevalence and Association With Serum Albumin and Brain Natriuretic Peptide.

Clemens M Ortner et al.

Anesthesia and analgesia, 128(6), 1208-1216 (2019-05-17)

Pilot studies applying point-of-care ultrasound (POCUS) in preeclampsia indicate the presence of pulmonary interstitial edema, cerebral edema, and cardiac dysfunction. Laboratory markers of oncotic pressure (albumin) and cardiac dysfunction (brain natriuretic peptide [BNP]) may be abnormal, but the clinical application

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