4 carboxyphenylboronic acid

Manufactured by Merck Group

Sourced in Japan, United Kingdom, United States

4-carboxyphenylboronic acid is a chemical compound used as a laboratory reagent. It is a colorless crystalline solid with the chemical formula C₆H₇BO₃. The compound contains a boronic acid functional group attached to a benzene ring with a carboxyl group. It is commonly used in organic synthesis and as a building block for various chemical reactions.

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4 protocols using 4 carboxyphenylboronic acid

Mesoporous Silica Nanoparticle Synthesis

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Tetraethyl orthosilicate (TEOS, Aldrich) was used as silica source.
Cetyltrimethylammonium chloride (CTAC, 25% aqueous solution, Aldrich) was used for
as a structure-directing agent, and triethanolamine (TEA, Aldrich) as an catalyst
and gelator. IR820, 4-carboxyphenylboronic acid, and
tetrakis(-triphenylphosphine)palladium were purchased from Sigma-Aldrich and used as
received. All the chemicals were used without further purification. Ultrapure
de-ionized (DI) water from Milli-Q ultrapure system was used for all synthesis,
dialysis, and storage steps.

Palantavida S., Tang R., Sudlow G.P., Akers W.J., Achilefu S, & Sokolov I. (2014). Ultrabright NIR fluorescent mesoporous silica nanoparticles. Journal of materials chemistry. B, 2(20), 3107-3114.

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Synthesis and Characterization of Insulin Derivatives

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Insulin (human, recombinant), sodium dodecyl sulfate, dimethylformamide, D-glucose, and D-fructose were purchased from Wako Pure Chemical Industries, Ltd. (Osaka, Japan). Tributylamine and isobutyl chloroformate were obtained from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). 4-Carboxyphenylboronic acid, 2,4,6-trinitrobenzenesulfonic acid (TNBS, 5% in water), 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES), and streptozotocin were purchased from Sigma-Aldrich Japan (Tokyo, Japan). A bottle of preserved sheep blood diluted with an equal volume of Alsever’s solution was obtained from Kohjin Bio Co., Ltd. (Saitama, Japan). Alsever’s solution contains 2.05% glucose, 0.8% sodium citrate, 0.055% citric acid, and 0.42% sodium chloride. The preserved blood is described here as “blood (1/2)” in accordance with the dilution ratio.

Ohno Y., Kawakami M., Seki T., Miki R., Seki T, & Egawa Y. (2019). Cell Adhesive Character of Phenylboronic Acid-Modified Insulin and Its Potential as Long-Acting Insulin. Pharmaceuticals, 12(3), 121.

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Synthesis and Characterization of Glycerol Monomethacrylate Copolymers

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Glycerol monomethacrylate (GMA; 99.8%) was donated by GEO Specialty Chemicals (Hythe, UK) and was used without further purification. 2-Hydroxypropyl methacrylate (HPMA) was purchased from Alfa Aesar (UK) and was used as received. 4,4′-Azobis(4-cyanopentanoic acid) (ACVA; V-501; 99%), 2,2′-azobisisobutyronitrile (AIBN), 2-cyano-2-propyl dithiobenzoate (CPDB), 4-carboxyphenylboronic acid (CPBA; ≥90%), ethanol (99%, anhydrous grade), methanol, and dichloromethane were purchased from Sigma-Aldrich (UK) and were used as received. Deuterated methanol (CD₃OD) was purchased from Goss Scientific (Nantwich, UK). Buffer solutions were purchased from Thermo Fisher Scientific (Chelmsford, USA). All solvents were HPLC-grade and were purchased from Fisher Scientific (Loughborough, UK).

Deng R., Ning Y., Jones E.R., Cunningham V.J., Penfold N.J, & Armes S.P. (2017). Stimulus-responsive block copolymer nano-objects and hydrogels via dynamic covalent chemistry †Electronic supplementary information (ESI) available: GPC date, additional TEM images and DLS data. See DOI: 10.1039/c7py01242j. Polymer Chemistry, 8(35), 5374-5380.

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Phenylboronate-modified Amino Column Preparation

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Analysis was performed on an HPLC Agilent 1100 LC system (Agilent, Palo Alto, CA, USA) consisting of a degasser, binary pump, autosampler, thermostatted column compartment, and multi-wavelength detector. The amido column used here was a core-shell particle column with amide polyol and TMS end-capping (2.6 µm particles, 150 × 2.1 mm, bioZen Glycan, Phenomenex, Torrance, CA, USA). The amino column was a 3-aminopropyl silica SilaSpher Amine (5 µm, 12 nm pore, 100 × 3 mm, Silicycle, QC, Canada). The detection wavelength was 230 nm, and the separation temperature was 25 • C. The mobile phase was 50 (amino column) or 25 mmol/L (amido column) phosphate buffer, pH 4.25 (NaH 2 PO 4 •2H 2 O titrated by H 3 PO 4 ), at a flow rate of 0.25 mL/min.
A phenylboronate-modified amino column (using the SilaSpher Amine) was prepared using a Ugi four-component reaction [19] (link) based on a "one-pot" reaction of an equimolar mixture of primary amine (3-aminopropyl silica), aldehyde (benzaldehyde, Sigma-Aldrich, St. Louis, MO, USA), isocyanide (tert-butyl isocyanide, Sigma-Aldrich, St. Louis, MO, USA), and carboxylic acid (4-carboxyphenylboronic acid, Sigma-Aldrich, St. Louis, MO, USA) in methanol (Penta, Praha, Czech Republic).

Mikšı́k I., Kubinová Š., Morvan M., Výborný K., Tatar A., Král V., Záruba К., & Sýkora D. (2020). Analysis of Chondroitin/Dermatan Sulphate Disaccharides Using High-Performance Liquid Chromatography. Separations, 7(3), 49-49.

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