(3-Acrylamidophenyl)Boronic Acid

• CAS: 99349-68-5
• Catalog Number: ACM99349685
• Category: Main Products
• Molecular Weight: 190.99
• Molecular Formula: C9H10BNO3
• Synonyms: [3-(prop-2-enoylamino)phenyl]boronic acid
• Melting Point: 245-255 °C
• Appearance: White to off-white powder

Case Study

(3-Acrylamidophenyl)Boronic Acid as a Hydrophilic Functional Monomer for Boronate Affinity Monolithic Capillaries

Wang, Xin, et al. Analytical Methods 5.20 (2013): 5444-5449.

Boronate affinity chromatography is a powerful technique for selectively capturing cis-diol-containing biomolecules such as glycoproteins and nucleosides. In this study, (3-acrylamidophenyl)boronic acid (APBA) was employed as a hydrophilic functional monomer, copolymerized with the hydrophilic cross-linker N,N'-methylenebisacrylamide (MBAA) to prepare a novel boronate affinity monolithic capillary via in situ polymerization.
APBA offers three key advantages: its amide group enhances hydrophilicity, its pKa (8.2) is lower than that of the widely used 4-vinylphenylboronic acid (VPBA, pKa 8.9), and its slightly longer spacer arm improves ligand accessibility.
Key Results:
· The poly(APBA-co-MBAA) monolith completely suppressed reversed-phase retention: no retention of alkylbenzenes (benzene to propylbenzene) was observed under conditions where other monoliths showed significant hydrophobic interactions (e.g., VPBA-EDMA gave retention factors of 0.1-1.2).
· The monolith exhibited the highest binding capacity for adenosine among all compared materials: 19.4 μmol/mL at pH 9.0 (vs. 10.8 for VPBA-EDMA and 9.6 for VPBA-MBAA), despite having the lowest specific surface area (3.7 m²/g).
· Due to APBA's lower pKa, the monolith captured nucleosides at near-physiological pH (7.5), whereas VPBA-based monoliths required pH 8.5. Adenosine was retained at pH 7.5 and eluted at pH 2.7, while deoxyadenosine (lacking cis-diol) showed no retention.
· The monolith demonstrated excellent selectivity for glycoproteins: horseradish peroxidase, RNase B, and lactoferrin were captured at pH 8.5, while non-glycoproteins (BSA, myoglobin) passed through unretained.

(3-Acrylamidophenyl)Boronic Acid as a Functional Comonomer for Water-Soluble Carbohydrate Sensors

Liang, Xiaoli, et al. ACS Applied Polymer Materials 1.6 (2019): 1341-1349.

In this work, (3-acrylamidophenyl)boronic acid (AAPBA) was copolymerized with tert-butyl methacrylate via free radical polymerization, followed by hydrolysis to yield a water-soluble poly(methacrylic acid)-co-AAPBA (PMAA-co-AAPBA) copolymer containing 6% boronic acid moieties (Mw = 40,500 g/mol, Đ = 1.2).
The copolymer forms a supramolecular complex with oxidized hematoxylin (HT) dye in neutral aqueous buffer (50 mM HEPES, pH 7.4). Addition of carbohydrates displaces HT, producing optical signal changes exploited in an indicator displacement assay (IDA). Multivariate analysis (linear discriminant analysis, LDA) of absorbance data enables carbohydrate discrimination.
Key Results:
· PMAA-co-AAPBA exhibits excellent water solubility across a wide pH range due to hydrophilic PMAA segments, overcoming the poor aqueous solubility of isolated boronic acids. The [PMAA-co-AAPBA·HT] complex responds differentially to eight mono- and disaccharides (fructose, ribose, glucose, galactose, maltose, lactose, sucrose, trehalose) at physiological pH, with LDA achieving complete discrimination (100% correct classification).
· Binding affinity correlates with sugar ring structure: fructose and ribose (predominantly furanose, five-membered rings) cluster near free HT (high displacement), while glucose, galactose, and disaccharides (pyranose, six-membered rings) remain near the bound complex (low displacement).
· (3-Acrylamidophenyl)boronic acid thus serves as an effective functional comonomer for constructing water-soluble polymeric sensors, enabling carbohydrate discrimination at physiological pH through differential boronate affinity.

(3-Acrylamidophenyl)Boronic Acid as a Functional Monomer for Glucose-Responsive Block Glycopolymer Hydrogels in Insulin Delivery

Cai, Baoqi, et al. Carbohydrate research 445 (2017): 32-39.

Self-regulated insulin delivery systems that respond to blood glucose levels offer a promising approach for diabetes treatment. Phenylboronic acid and its derivatives can reversibly bind with cis-diols including glucose. In this study, (3-acrylamidophenyl)boronic acid (APBA) was copolymerized with 2-lactobionamidoethyl methacrylate (LAMA) via RAFT polymerization to form block glycopolymer hydrogels crosslinked through dynamic boronic ester bonds between APBA and the diol groups of LAMA. Swelling behavior, insulin loading capacity, glucose-responsive release, and cytotoxicity were evaluated.
Key Results:
· Hydrogel formation occurred only at specific p(APBA):LAMA molar ratios (1:2 to 3:2), with yields up to 94%. SEM revealed highly porous sponge-like structures facilitating drug loading and release.
· Swelling ratios in PBS (pH 7.4) reached 1856% for p(APBA1-b-LAMA2) within 10 min, increasing with LAMA content due to enhanced charged phenylborate hydrophilicity.
· Insulin loading capacity reached 15.6%, correlating with LAMA content. Cumulative release over 48 h ranged from 69-84%, decreasing with higher LAMA content due to increased crosslinking density.
· The hydrogel exhibited glucose-dependent release: in 3 mg/mL glucose, insulin release increased from 69% to 81%; switching from 0 to 3 mg/mL glucose triggered immediate accelerated release via competitive displacement of LAMA by glucose. MTT assays showed >90% NIH3T3 cell viability at all tested concentrations, with carbohydrate moieties enhancing cytocompatibility.

Custom Q&A

What is the molecular formula of (3-Acrylamidophenyl)Boronic Acid?

The molecular formula is C9H10BNO3.

What is the molecular weight of (3-Acrylamidophenyl)Boronic Acid?

The molecular weight is 190.99 g/mol.

When was (3-Acrylamidophenyl)Boronic Acid created?

It was created on October 25, 2006.

What is the IUPAC name of (3-Acrylamidophenyl)Boronic Acid?

The IUPAC name is [3-(prop-2-enoylamino)phenyl]boronic acid.

What is the InChI of (3-Acrylamidophenyl)Boronic Acid?

The InChI is InChI=1S/C9H10BNO3/c1-2-9(12)11-8-5-3-4-7(6-8)10(13)14/h2-6,13-14H,1H2,(H,11,12).

What is the InChIKey of (3-Acrylamidophenyl)Boronic Acid?

The InChIKey is ULVXDHIJOKEBMW-UHFFFAOYSA-N.

What is the canonical SMILES of (3-Acrylamidophenyl)Boronic Acid?

The canonical SMILES is B(C1=CC(=CC=C1)NC(=O)C=C)(O)O.

What is the CAS number of (3-Acrylamidophenyl)Boronic Acid?

The CAS number is 99349-68-5.

How many hydrogen bond donor counts does (3-Acrylamidophenyl)Boronic Acid have?

It has 3 hydrogen bond donor counts.

What is the topological polar surface area of (3-Acrylamidophenyl)Boronic Acid?

The topological polar surface area is 69.6 Ų.