Name: 11-Azidoundecanoic acid
Brand: BOC Sciences
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Synonyms

11-Azido-undecanoic acid

SMILES

C(CCCCCN=[N+]=[N-])CCCCC(=O)O

InChI

InChI=1S/C11H21N3O2/c12-14-13-10-8-6-4-2-1-3-5-7-9-11(15)16/h1-10H2,(H,15,16)

InChIKey

LXAVFOAOGZWQKT-UHFFFAOYSA-N

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11-Azidoundecanoic acid, a versatile compound with unique chemical properties, finds applications across bioscience and materials science. Here are four key applications presented with high perplexity and burstiness:

Bioconjugation: Serving as a cornerstone in bioconjugation techniques, 11-Azidoundecanoic acid facilitates the attachment of biomolecules to surfaces or other biomolecules. Its azide group enables precise and efficient conjugation via click chemistry, unlocking avenues for studying protein interactions, enzyme activities, and cell surface modifications. This indispensable application plays a pivotal role in the development of diagnostic tools and therapeutic delivery systems, driving innovation in biomedicine.

Material Science: In the realm of material science, 11-Azidoundecanoic acid plays a vital role in surface modification, enhancing material properties such as hydrophobicity, conductivity, and bioactivity by introducing functional groups. Through click chemistry with alkyne-modified surfaces, customized nanomaterials and coatings can be crafted, elevating material performance in biomedical devices, sensors, and other cutting-edge applications. This innovation reshapes the landscape of material engineering, ushering in new possibilities for advanced technologies.

Polymer Chemistry: Embracing controlled radical polymerization techniques, 11-Azidoundecanoic acid is a key player in the synthesis of functional polymers. Its azide functionality allows for post-polymerization modifications, facilitating the incorporation of diverse functional groups. This capability is instrumental in designing intelligent polymers with tailored properties for applications in drug delivery, tissue engineering, and responsive materials, revolutionizing the field of polymer chemistry with its versatility and precision.

Chemical Biology: In the realm of chemical biology, 11-Azidoundecanoic acid serves as a vital chemical reporter for investigating biological processes. Through its integration into biomolecules, it serves as a tracer for molecular interactions and dynamics within cells, offering invaluable insights into cellular mechanisms, protein functions, and metabolic pathways. This technique deepens our comprehension of complex biological systems, pushing the boundaries of knowledge in chemical biology and paving the way for groundbreaking discoveries.

1. Functionalization of surfactant wrapped graphene nanosheets with alkylazides for enhanced dispersibility

Sajini Vadukumpully, Jhinuk Gupta, Suresh Valiyaveettil, Yongping Zhang, Guo Qin Xu Nanoscale . 2011 Jan;3(1):303-8. doi: 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.

2. Functionalization of MgZnO nanorod films and characterization by FTIR microscopic imaging

Elena Galoppini, Pavel Ivanoff Reyes, Keyang Yang, Rui Li, Yicheng Lu, Carol Flach, Qihong Zhang, Richard Mendelsohn, Guangyuan Li, Yuan Chen Anal Bioanal Chem . 2017 Nov;409(27):6379-6386. doi: 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 MgZnOnanowas used instead of pure ZnO to take advantage of the etching resistance of the MgZnOnanoduring 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 MgZnOnanosurface 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 MgZnOnanomorphology. 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/MgZnOnanofilms 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.