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11-Azidoundecanoic acid

目录号 : GC68204

11-Azidoundecanoic acid 是一种含有叠氮基团的化学试剂,是一种疏水生物偶联剂。11-Azidoundecanoic acid 作为疏水生物偶联剂,可在叠氮位置使用 Staudinger 结扎法或 Click-chemistry 进一步修饰。11-Azidoundecanoic acid 是硫辛酸连接酶 (LpIA) 的标记底物。

11-Azidoundecanoic acid Chemical Structure

Cas No.:118162-45-1

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产品描述

11-Azidoundecanoic acid is a click chemistry reagent containing an azide group. 11-Azidoundecanoic acid acts as a hydrophobic bioconjugation linker that can be further modified at the azido-position using Staudinger ligation or Click-chemistry. 11-Azidoundecanoic acid is substrate of lipoic acid ligase (LpIA) for labeling[1][2].

The microbial lipoic acid ligase (LplA) can specifically attach an alkyl azide onto an engineered LplA acceptor peptide (LAP). Then the alkyl azide selectively derivatizes with cyclooctyne conjugates to various probes[1].
LplA method should provide general access to biochemical and imaging studies of cell surface proteins, using small fluorophores introduced via a short peptide tag[1].

[1]. FernÁndez-SuÁrez M, et al. Redirecting lipoic acid ligase for cell surface protein labeling with small-molecule probes. Nat Biotechnol. 2007 Dec;25(12):1483-7.
[2]. Heal WP, et al. N-Myristoyl transferase-mediated protein labelling in vivo. Org Biomol Chem. 2008 Jul 7;6(13):2308-15.

Chemical Properties

Cas No. 118162-45-1 SDF Download SDF
分子式 C11H21N3O2 分子量 227.3
溶解度 DMSO : 100 mg/mL (439.95 mM; Need ultrasonic) 储存条件 4°C, protect from light
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1 mM 4.3995 mL 21.9974 mL 43.9947 mL
5 mM 0.8799 mL 4.3995 mL 8.7989 mL
10 mM 0.4399 mL 2.1997 mL 4.3995 mL
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Research Update

Functionalization of surfactant wrapped graphene nanosheets with alkylazides for enhanced dispersibility

Nanoscale 2011 Jan;3(1):303-8.PMID:21052576DOI:10.1039/c0nr00547a.

A facile and simple approach for the covalent functionalization of surfactant wrapped graphene sheets is described. The approach involves functionalization of dispersible graphene sheets with various alkylazides and 11-Azidoundecanoic acid proved the best azide for enhanced dispersibility. The functionalization was confirmed by infrared spectroscopy and scanning tunneling microscopy. The free carboxylic acid groups can bind to gold nanoparticles, which were introduced as markers for the reactive sites. The interaction between gold nanoparticles and the graphene sheets was followed by UV-vis spectroscopy. The gold nanoparticle-graphene composite was characterized by transmission electron microscopy and atomic force microscopy, demonstrating the uniform distribution of gold nanoparticles all over the surface. Our results open the possibility to control the functionalization on graphene in the construction of composite nanomaterials.

Functionalization of MgZnO nanorod films and characterization by FTIR microscopic imaging

Anal Bioanal Chem 2017 Nov;409(27):6379-6386.PMID:28840290DOI:10.1007/s00216-017-0577-2.

Metal organic chemical vapor deposition grown films consisting of MgxZn1-xO (4% < x < 5%) nanorod arrays (MgZnOnano) were functionalized with 11-Azidoundecanoic acid (1). The MgZnOnano was used instead of pure ZnO to take advantage of the etching resistance of the MgZnOnano during the binding and subsequent sensing device fabrication processes of sensor devices, while the low Mg composition level ensures that selected ZnO properties useful for sensors development, such as piezoelectricity, are retained. Compound 1 was bound to the MgZnOnano surface through the carboxylic acid group, leaving the azido group available for click chemistry and as a convenient infrared spectroscopy (IR) probe. The progress of the functionalization with 1 was characterized by FTIR microscopic imaging as a function of binding time, solvents employed, and MgZnOnano morphology. Binding of 1 was most stable in solutions of 3-methoxypropionitrile (MPN), a non-protic polar solvent. This occurred first in μm-scale islands, then expanded to form a rather uniform layer after 22 h. Binding in alcohols resulted in less homogenous coverage, but the 1/MgZnOnano films prepared from MPN were stable upon treatment with alcohols at room temperature. The binding behavior was significantly dependent on the surface morphology of MgZnOnano. Graphical abstract The functionalization of MgZnO nanorod films with a click-ready linker and its dependence on bidning conditions and morphology has been studied by FTIR microscopic imaging using the azido group as the IR tag.