2-Acetylphenylboronic acid (308103-40-4)
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Description
Antibiotic resistance of bacterial pathogens poses an increasing threat to the wellbeing of our society and urgently calls for new strategies for infection diagnosis and antibiotic discovery. The antibiotic resistance problem at least partially arises from extensive use of broad-spectrum antibiotics. Ideally, for the treatment of infection, one would like to use a narrow-spectrum antibiotic that specifically targets and kills the disease-causing strain. This is particularly important considering the commensal bacterial species that are beneficial and sometimes even critical to the health of a human being. Screening of the library against live bacterial cells yields submicromolar and highly specific binders for clinical strains of Staphylococcus aureus and Acinetobacter baumannii that display antibiotic resistance.
Bioorthogonal conjugation chemistry has enabled the development of tools for the interrogation of complex biological systems. Although a number of bioorthogonal reactions have been documented in literature, they are less ideal for one or several reasons including slow kinetics, low stability of the conjugated product, requirement of toxic catalysts, and side reactions with unintended biomolecules. The boronic acid moiety greatly accelerates the initial formation of a semicarbazone conjugate, which rearranges into a stable diazaborine. The diazaborine formation can be performed in blood serum or cell lysates with minimal interference from biomolecules. A synthetic amino acid D-AB3, which presents a 2-acetylphenylboronic acid moiety as its side chain, was found to incorporate into several bacterial species through cell wall remodeling, with particularly high efficiency for Escherichia coli. Subsequent D-AB3 conjugation to a fluorophore-labeled semicarbazide allows robust detection of this bacterial pathogen in blood serum.
2-Acetylphenylboronic acid (308103-40-4) Specifications
| CAS | 308103-40-4 |
| CAS Min % | 95.0 |
| CAS Max % | 100.0 |
| MDL Number | MFCD01321263 |
| InChI Key | ZKAOVABYLXQUTI-UHFFFAOYSA-N |
| Chemical Name or Material | 2-Acetylphenylboronic acid |
| Infrared Spectrum | Authentic |
| Assay Percent Range | 96% |
| Physical Form | Powder or Chunks |
| Packaging | Glass bottle |
| Molecular Formula | C8H9BO3 |
| Molecular Weight (g/mol) | 163.967 |
| SMILES | B(C1=CC=CC=C1C(=O)C)(O)O |
| Color | Yellow |
| Chemical Name or Material | 2-Acetylphenylboronic acid |
| Melting Point | 170.0°C |
| Assay | 96% |
2-Acetylphenylboronic acid (308103-40-4) Safety and Handling
(308103-40-4) Hazard description:
Causes serious eye irritation.
Causes skin irritation.
May cause respiratory irritation.
Avoid breathing dust/fume/gas/mist/vapors/spray.
2-Acetylphenylboronic acid Precautionary statement:
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.
WARNING: The information provided on this web site was developed in compliance with European Union (EU) regulations and is correct to the best of our knowledge, information and belief at the date of its publication. The information given is designed only as a guide for safe handling and use. It is not to be considered as either a warranty or quality specification.
2-Acetylphenylboronic acid (308103-40-4) Articles
Arylboronic Acids
Aldrich is pleased to present its complete selection of arylboronic acids, the building blocks of the Suzuki coupling experiment…
Aldrich ChemFiles 2001,
Boronic Acids
Most boronic acids readily undergo dehydration reactions to give a cyclic (trimer) anhydride…
Aldrich ChemFiles 2007,
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