1H Nuclear Magnetic Resonance Research Articles

Synthesis and Conformational Dynamics of Selenanthrene (Oxides): Establishing an Energetic Flexibility Index for Scaffolds.

The use of new dynamic scaffolds for constructing inorganic and organometallic complexes with enhanced reactivities is an important new research direction. Toward this fundamental aim, an improved synthesis of the dynamic scaffold selenanthrene, along with its monoxide, trans-dioxide and the previously unknown trioxide, is reported. A discussion of the potential reaction mechanism for selenanthrene is provided, and all products were characterized using 1H, 13C, and 77Se nuclear magnetic resonance (NMR) spectroscopy and single-crystal X-ray crystallography. The dynamic ring inversion processes (i.e., "butterfly motion") for selenanthrene and its oxides were investigated using variable-temperature 1H NMR and density functional theory calculations. The findings suggest that selenanthrene possesses a roughly equal barrier to inversion as its sulfur analogue, thianthrene. However, selenanthrene oxides evidently possess larger inversion barriers as compared to their sulfur analogues due to the enhanced electrostatic intramolecular interactions inherent between the highly polar selenium-oxygen bond and adjacent C-H moieties. Finally, we propose a quantitative "flexibility index" in deg/(kcal/mol) for various tricyclic scaffolds to provide researchers with a comparative scale of dynamic motion across many different systems.

Formation and Fluorescent Mechanism of Multiple Color Emissive Carbon Dots from o-Phenylenediamine.

Carbon dots (CDs) have received considerable attention in many application areas owing to their unique optical properties and potential applications; however, the fluorescent mechanism is an obstacle to their applications. Herein, three-color emissive CDs are prepared from single o-phenylenediamine (oPD) by regulating the ratio of ethanol and dimethylformamide (DMF). Fluorescent mechanism of these CDs is proposed as molecular state fluorescence. Reaction intermediates are identified using liquid chromatrography-mass spectroscopy (LC-MS) and 1H nuclear magnetic resonance (NMR) spectra. 1H-Benzo[d]imidazole (BI), 2,3-diaminophenazine (DAP), and 5,14-dihydroquinoxalino[2,3-b] phenazine (DHQP) are proposed to be the fluorophores of blue, green, and red emissive CDs by comparing their optical properties. As per the LC-MS and 1H-NMR analysis, DHQP with red emission tends to form from DAP and oPD in pure ethanol. By adding DMF, BI formation is enhanced and DHQP formation is suppressed. The prepared CDs exhibit green emission with DAP. When the DMF amount is >50%, BI formation is considerably promoted, resulting in DAP formation being suppressed. BI with blue emission then turns into the fluorophore of CDs. This result provides us an improved understanding of the fluorescent mechanism of oPD-based CDs, which guides us in designing the structure and optical properties of CDs.

Development and Validation of 1H Nuclear Magnetic Resonance Quantitative Method for Efavirenz API Quality Control

Development and Validation of 1H Nuclear Magnetic Resonance Quantitative Method for Efavirenz API Quality Control

Identification and Molecular Docking Analysis of Angiotensin-Converting Enzyme Inhibitors from Finger Millet (Eleusine coracana).

Hypertension remains a significant global health concern, contributing significantly to cardiovascular diseases and mortality rates. The inhibition of angiotensin-converting enzyme (ACE) plays a crucial role in alleviating high blood pressure. We investigated the potential of finger millets (Eleusine coracana) as a natural remedy for hypertension by isolating and characterizing its ACE-inhibitory compound. First, we evaluated the ACE-inhibitory activity of the finger millet ethanol extract and subsequently proceeded with solvent fractionation. Among the solvent fractions, the ethyl acetate fraction exhibited the highest ACE inhibitory activity and was further fractionated. Using preparative high-performance liquid chromatography, the ethyl acetate fraction was separated into four subfractions, with fraction 2 (F2) exhibiting the highest ACE inhibitory activity. Subsequent 1H-nuclear magnetic resonance (NMR) and 13C-NMR analyses confirmed that the isolated compound from F2 was catechin. Furthermore, molecular docking studies indicated that catechin has the potential to act as an ACE inhibitor. These findings suggest that finger millets, particularly as a source of catechin, have the potential to be used as a natural antihypertensive.

Emulsions Stabilized with an Electrostatic Complex of Quaternized Cellulose Nanofiber and Octanoyl Gelatin and the Effect of pH Value on Their Stability

Emulsions Stabilized with an Electrostatic Complex of Quaternized Cellulose Nanofiber and Octanoyl Gelatin and the Effect of pH Value on Their Stability

Dipolar Order Induced Electron Spin Hyperpolarization.

The structure of coupled electron spin systems is of fundamental interest to many applications, including dynamic nuclear polarization (DNP), enhanced nuclear magnetic resonance (NMR), the generation of electron spin qubits for quantum information science (QIS), and quantitative studies of paramagnetic systems by electron paramagnetic resonance (EPR). However, the characterization of electron spin coupling networks is nontrivial, especially at high magnetic fields. This study focuses on a system containing high concentrations of trityl radicals that give rise to a DNP enhancement profile of 1H NMR characteristic of the presence of electron spin clusters. When this system is subject to selective microwave saturation through pump-probe ELectron DOuble Resonance (ELDOR) experiments, electron spin hyperpolarization is observed. We show that the generation of an out-of-equilibrium longitudinal dipolar order is responsible for the transient hyperpolarization of electron spins. Notably, the coupled electron spin system needs to form an AX-like system (where the difference in the Zeeman interactions of two spins is larger than their coupling interaction) such that selective microwave irradiation can generate signatures of electron spin hyperpolarization. We show that the extent of dipolar order, as manifested in the extent of electron spin hyperpolarization generated, can be altered by tuning the pump or probe pulse length, or the interpulse delay in ELDOR experiments that change the efficiency to generate or readout longitudinal dipolar order. Pump-probe ELDOR with selective saturation is an effective means for characterizing coupled electron spins forming AX-type spin systems that are foundational for DNP and quantum sensing.

Design, Synthesis, and Biological Activity of Novel Triketone-Containing Phenoxy Nicotinyl Inhibitors of HPPD.

4-Hydroxyphenylpyruvate dioxygenase (HPPD) is a crucial target enzyme in albino herbicides. The inhibition of HPPD activity interferes with the synthesis of carotenoids, blocking photosynthesis and resulting in bleaching and necrosis. To develop herbicides with excellent activity, a series of 3-hydroxy-2-(6-substituted phenoxynicotinoyl)-2-cyclohexen-1-one derivatives were designed via active substructure combination. The title compounds were characterized via infrared spectroscopy, 1H and 13C nuclear magnetic resonance spectroscopies, and high-resolution mass spectrometry. The structure of compound III-17 was confirmed via single-crystal X-ray diffraction. Preliminary tests demonstrated that some compounds had good herbicidal activity. Crop safety tests revealed that compound III-29 was safer than the commercial herbicide mesotrione in wheat and peanuts. Moreover, the compound exhibited the highest inhibitory activity against Arabidopsis thaliana HPPD (AtHPPD), with a half-maximal inhibitory concentration of 0.19 μM, demonstrating superior activity compared with mesotrione (0.28 μM) in vitro. A three-dimensional quantitative structure-activity relationship study revealed that the introduction of smaller groups to the 5-position of cyclohexanedione and negative charges to the 3-position of the benzene ring enhanced the herbicidal activity. A molecular structure comparison demonstrated that compound III-29 was beneficial to plant absorption and conduction. Molecular docking and molecular dynamics simulations further verified the stability of the complex formed by compound III-29 and AtHPPD. Thus, this study may provide insights into the development of green and efficient herbicides.

Preparation of β-cyclodextrin derivatives/metamizole inclusion complex nanofibers: Characterization, drug release, and wound scratch assay

Nanofibrous wound dressings fabricated by electrospinning have attracted significant research interest as they enable the controlled release of active substances at the wound site. The development of electrospun nanofibers with anti-inflammatory drugs, which demonstrate great potential for wound healing applications, is one of the main focuses of present research efforts. In this study, nanofibrous webs of 2-hydroxypropyl-β-cyclodextrin (HPβCD) and methyl-β-cyclodextrin (MβCD) loaded with metamizole (MMS) were fabricated by electrospinning. The prepared nanofibers were characterized by field-emission scanning electron microscopy, X-ray diffraction, Fourier-transform infrared spectroscopy, thermogravimetric/differential thermal analysis, 1H nuclear magnetic resonance spectroscopy, ultraviolet diffuse reflectance spectroscopy, and photoluminescence analysis. The interactions of HPβCD and MβCD with MMS in aqueous solutions were studied using absorption and fluorescence spectroscopy, and the 1:1 MMS/CD inclusion complexes were theoretically analyzed at the PM3 level of theory. Furthermore, the drug release, biocompatibility, and wound scratch assay of the nanofibers were evaluated. In vitro drug release analysis revealed controllable release of MMS from the nanofibers. The CD nanofibers loaded with MMS showed good biocompatibility with skin fibroblasts. An in vitro wound scratch assay indicated that the nanofibers promoted fast wound closure with a rate of 98.66 ± 3.9%. In summary, the prepared nanofibrous webs are promising candidates for wound-dressing applications.

Metabolome in Tibialis and Soleus Muscles in Wild-Type and Pin1 Knockout Mice through High-Resolution Magic Angle Spinning 1H Nuclear Magnetic Resonance Spectroscopy

Skeletal muscles are heterogenous tissues composed of different myofiber types that can be classified as slow oxidative, fast oxidative, and fast glycolytic which are distinguished on the basis of their contractile and metabolic properties. Improving oxidative metabolism in skeletal muscles can prevent metabolic diseases and plays a protective role against muscle wasting in a number of neuromuscular diseases. Therefore, achieving a detailed understanding of the factors that regulate myofiber metabolic properties might provide new therapeutic opportunities for these diseases. Here, we investigated whether peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (PIN1) is involved in the control of myofiber metabolic behaviors. Indeed, PIN1 controls glucose and lipid metabolism in a number of tissues, and it is also abundant in adult skeletal muscles; however, its role in the control of energy homeostasis in this tissue is still to be defined. To start clarifying this topic, we compared the metabolome of the tibialis anterior muscle (mainly glycolytic) and soleus muscle (oxidative) in wild-type and Pin1 knockout mice with High-Resolution Magic Angle Spinning (HR-MAS) NMR on intact tissues. Our analysis reveals a clear demarcation between the metabolomes in the two types of muscles and allows us to decode a signature able to discriminate the glycolytic versus oxidative muscle phenotype. We also detected some changes in Pin1-depleted muscles that suggest a role for PIN1 in regulating the metabolic phenotype of skeletal muscles.

Chemoreactome screening of aquacobalamin and heptamethyl ester of cyanoaquacobyrinic acid cytotoxic effects on tumor cells with experimental confirmation on BT-474 and A549 cell

Background. The search for an effective and safe pharmacotherapy for tumor diseases includes the evaluation of the action of candidate molecules on various types of tumor cells. Vitamin B12 and its derivatives are promising molecules whose properties can be controlled through chemical modifications.Objective: conducting in silico chemoreactom screening and in vitro experimental study of aquacobalamin and heptamethyl ester of cyanoaquacobyrinic acid (HECСA).Material and methods. Chemoreactome screening was carried out on the basis of a problem-oriented theory of chemograph isomorphism analysis, which is an extension of the algebraic approach to machine learning and recognition problems. Trainable algorithms for calculating chemical distances between molecules were used, on the basis of which the values of half-maximal inhibitory concentration (IC50) were calculated. Screening was carried out for 470 cultures of human tumor cells, including SNB19 (astrocytoma), HCT116 (colon cancer), HeLa (cervical carcinoma), BT-474 (breast duct carcinoma), and A549 (lung carcinoma) cell lines. Dicyanocobyric acid heptamethyl ester ((CN)2Cby(OCH3)7) was obtained by boiling a solution of vitamin B12 in methanol with sulfuric acid (1.0 M) for 4 days. HECСA ((CN)(H2O)Cby(OCH3)7) was obtained by vacuum drying an aqueous solution of (CN)2Cby(OCH3)7 (pH 4.0 and 25 °С). The ester structure and purity were confirmed by 1H nuclear magnetic resonance data, elemental analysis, and MALDI-ToF (matrix-assisted laser desorption/ionization time of flight) mass spectroscopy. Experimental studies of tumor cell cultures were carried out using the MTT testwith aquacobalamin and HECСA on cell lines of immortalized (telomerized) fibroblasts (Fb-hTERT), lung carcinoma (A549), and breast duct cancer (BT-474).Results. Chemoreactome screening of the effects of molecules on tumor cells made it possible to obtain estimates of cell growth IC50 for 470 tumor cell lines. Depending on cell line and vitamin B12 derivative molecule, IC50 values varied in a fairly wide range: from 15 to 2000 nM. In vitro studies on cultures of two human tumor cell lines (BT-474 and A549) and telomerized Fb-hTERT fibroblasts confirmed the cytotoxic effect of aquacobalamin and its hydrophobic derivative HECСA. It was shown that aquacobalamin had weak cytotoxic properties in the concentration range of 3.125–200 µg/l (IC50 > 200 nM), and HECСA significantly reduces the survival of BT-474 and A549 tumor cell lines at high concentrations (100–200 µg/l, IC50 about 100 nM).Conclusion. Correspondence was shown between the results of in silico chemoreactome screening and in vitro cell culture studies: IC50 values for HECСA were significantly lower than for aquacobalamin, and the conversion factor from chemoreactome estimates to experimental ones was almost the same (2.64 for BT-474, and 2.63 for A549). The results of chemoreactome screening for other tumor cell lines can be used to plan further cell experiments with vitamin B12 derivatives.

Pillarurilarenes: Glycoluril-Expanded Pillararenes.

Glycoluril-expanded pillararenes composed of glycoluril and dialkoxybenzene units, namely, pillarurilarenes (PURA), were synthesized through a fragment coupling macrocyclization strategy. Partial replacement of dialkoxybenzene with glycoluril endows PURA with polarized equatorial methine protons for derivatization or CH-anion binding. Crystal structures of pillar[2]uril[4]arene and pillar[1]uril[4]arene containing two glycoluril units and one glycoluril unit, respectively, indicated the inward orientation of the glycoluril unit, as also suggested by 1H nuclear magnetic resonance and density functional theory calculation. This work lays a good foundation for expanding pillararenes using non-aromatic rings.

One pot green synthesis of Biginelli reaction catalysed by bio-waste metal-free super acid lignin sulphonate

A Bio-waste metal-free super acid catalyst (BWC) has been synthesized at higher temperature and used as a catalyst for synthesis of 3,4-dihydropyrimidine-2-(1H)-ones (DHPMs) via one pot three component Biginelli reaction. The multicomponent reactions are very complex and involves more than two reagents. In the present study, sulfonated carbonaceous material called a green catalyst was utilized for three component reaction. Catalyst was synthesized from sodium lignosulfonate which is obtained from the wastage of paper-making industries from the sulfite pulping process. The synthesized green catalyst was characterized by FT-IR, Thermal Gravimetric Analysis (TGA) scanning electron microscopy (SEM), Thermal Electronic microscopy (TEM), and elemental analysis. The three component Biginelli synthesis the catalyst was optimized to 8 mol % quantity which was sufficient to complete the reaction within 1–4 hrs. The yield of reaction ranges from 70-90 %. Separation was easy and recycling ability of catalyst was also tested with good retention of catalytical activity. Catalytic activity was performed as an acid-catalyzed reaction in ethanol. The synthesis of all the compounds were confirmed by 1H NMR (Nuclear magnetic resonance), MS (Mass Spectra), FT-IR (Fourier Transform Infrared), CHNS (Carbo, Hydrogen, Nitrogen, Sulphur) analysis. The satisfactory results were obtained with good yields, shorter reaction time and simplicity in the experimental procedure. The catalysts could be recycled and reused three times without decrease in the catalytic activity significantly.

Solubilization mechanism of α-glycosylated naringin based on self-assembled nanostructures and its application to skin formulation

We previously reported that α-glycosylated naringin (naringin-G), synthesized by enzyme-catalyzed transglycosylation, can enhance the solubility of poorly water-soluble compounds without surface-active property. However, the solubilization mechanism has not been fully elucidated. In this study, the solubilization mechanism of naringin-G was investigated using nuclear magnetic resonance (NMR) spectroscopy, and its application in skin formulations was further investigated. 1H NMR and dynamic light scattering measurements at various concentrations confirmed the self-assembled nanostructures of naringin-G above a critical aggregation concentration of approximately 2.2 mg/mL. Two-dimensional 1H–1H nuclear Overhauser effect spectroscopy and solubility tests revealed that flavone with poor water solubility, could be solubilized in its self-assembled structure with a stoichiometric relationship with naringin-G. When naringin-G was included in the skin formulation, the permeated amount and permeability coefficient (Papp) of flavones improved up to four times with increasing amounts of naringin-G. However, flavone solubilization by adding an excessive amount of naringin-G resulted in a decreased permeated amount and Papp of flavones, indicating the interplay between the apparent solubility and skin permeability of flavones. Naringin-G, which forms a nanoaggregate structure without exhibiting surface-active properties, has the potential to enhance the solubility and skin permeation of poorly water-soluble compounds.

Cumulative Data of 1H and 13C NMR Signals and Specific Rotations of Eremophilane Sesquiterpenoids. 4. 10H-3-O-Furanoeremophilanes

1H and 13C nuclear magnetic resonance (NMR) data and specific rotations of eremophilane sesquiterpenoids are cumulated as a series of review articles. This fourth chapter focuses on furanoeremophilanes bearing 10H with C-3 oxygen functionality, and 175 10H-furanoeremophilanes with 3-O functionality are listed in 38 tables. Those with 15,6-lactones and 6,15-ethers are included in this chapter. Dihydrofurans, lactols, dimers, nor- and seco-compounds, and other related compounds, are not included in this chapter. These data may help chemists working in the area of natural products chemistry and synthetic scientists as well as computational chemists.

Quantum-chemistry-computing and experimental development of a new n-alkenyl amino propionic and imino di-propionic acids-based gum inhibitor for gasoline

We present the quantum mechanics-based understanding about the formation of gums deposits in order to design, and then carry out the experimental synthesis of a detergent-dispersant (DD) gasoline additive base n-alkenyl imino di-propionic acid, obtained in mixture with its precursor base n-alkenyl amino propionic acid, aimed both to inhibit gums deposits within internal-combustion engines and maintain in suspension gums within gasoline. Density Functional Theory reveals the cohesion among gums agglomerates is mediated mainly through dispersion forces, that is, gums form supramolecular complexes; likewise, their affinity for oxidized metallic surfaces is predominantly due also to the dispersion forces, but intensified through the linking of the gums’ oxygens by the exposed metallic-surface irons, which is quantum driven to maximize irons spin through completing the truncated oxygen octahedral coordination, so providing to the gums’ adsorption a mixed chemisorption/physisorption character. Additionally, carbons from double bonds C C or from aromatic rings, as well as aminic hydrogens, contribute by means of weak semicovalent bonds to the gums’ chemisorption too. We take advantage of this acquired knowledge to outline a superior coordination chemistry than gums for the above deposits inhibitor, lying on the capability to form either trinuclear-tridentate or binuclear-bidentate surface complexes, reinforced moreover by a chelate composed of an iron-containing 6-membered ring. The additive was lab synthesized by means of an industrial-scale residues-less process, and characterized through 1H and 13C nuclear magnetic resonance along with infrared spectroscopy. The detergent performance, experimentally tested within the intake valve of a single-cylinder engine, shows that the DD additive inhibits up to 93.3% of the gums deposition.

Surgery for Crohn’s Disease Is Associated with a Dysbiotic Microbiome and Metabolome: Results from Two Prospective Cohorts

Background and AimsCrohn’s disease is associated with alterations in the gut microbiome and metabolome described as dysbiosis. We characterized the microbial and metabolic consequences of ileal resection, the most common Crohn’s disease surgery. MethodsPatients with and without intestinal resection were identified from the Diet to Induce Remission in Crohn’s Disease and Study of a Prospective Adult Research Cohort with Inflammatory Bowel Disease studies. Stool samples were analyzed with shotgun metagenomics sequencing. Fecal butyrate was measured with 1H nuclear magnetic resonance spectroscopy. Fecal bile acids and plasma 7α-hydroxy-4-cholesten-3-one (C4) was measured with mass spectrometry. ResultsIntestinal resection was associated with reduced alpha diversity and altered beta diversity with increased Proteobacteria and reduced Bacteroidetes and Firmicutes. Surgery was associated with higher representation of genes in the KEGG pathway for ABC transporters and reduction in genes related to bacterial metabolism. Surgery was associated with reduced concentration of the But gene but this did not translate to reduced fecal butyrate concentration. Surgery was associated with decreased abundance of bai operon genes, with increased plasma C4 concentration, increased primary bile acids and reduced secondary bile acids, including isoLCA. Additionally, E lenta, A equalofaciens and G pamelaeae were lower in abundance among patients with prior surgery in both cohorts. ConclusionsIn two different populations, prior surgery in Crohn’s disease is associated with altered fecal microbiome. Patients who had undergone ileal resection had reduction in the potentially beneficial bacteria E lenta and related actinobacteria as well as secondary bile acids, including isoLCA, suggesting that these could be biomarkers of patients at higher risk for disease progression.

Dynamics of Linkers in Metal-Organic Framework Glasses.

Metal-organic framework (MOF) glasses have emerged as a new class of organic-inorganic hybrid glass materials. Considerable efforts have been devoted to unraveling the macroscopic dynamics of MOF glasses by studying their rheological behavior; however, their microscopic dynamics remain unclear. In this work, we studied the effect of vitrification on linker dynamics in ZIF-62 by solid-state 2H nuclear magnetic resonance (NMR) spectroscopy. 2H NMR relaxation analysis provided a detailed picture of the mobility of the ZIF-62 linkers, including local restricted librations and a large-amplitude twist; these details were verified by molecular dynamics. A comparison of ZIF-62 crystals and glasses revealed that vitrification does not drastically affect the fast individual flipping motions with large-amplitude twists, whereas it facilitates slow cooperative large-amplitude twist motions with a decrease in the activation barrier. These observations support the findings of previous studies, indicating that glassy ZIF-62 retains permanent porosity and that short-range disorder exists in the alignment of ligands because of distortion of the coordination angle.

Synthesis of Dendrimer-Like Molecules with Partial Carbon Chain via Iterative Single Unit Monomer Insertions.

Carbon-chain dendritic polymers hold unique properties and promising applications. However, synthesizing carbon-chain dendrimers, beyond conjugated ones, remains a challenge. Here, the use of the iterative single unit monomer insertion technique for synthesizing 2.5 generation partial-carbon-chain dendrimers (G2.5) is described, utilizing bismaleimide as the core, a maleimide-trithiocarbonate conjugate as the branching unit, and indene as the spacer unit, following a divergent growth strategy. The optimized conditions for synthesizing the maleimide-trithiocarbonate branching unit are a bismaleimide to trithiocarbonate ratio of 5:1 and a reaction time of 30 min. The structures are verified using 1H nuclear magnetic resonance, gel permeation chromatography, and matrix-assisted laser desorption/ionization-time of flight mass spectra. A four-arm star polymer is then synthesized using the G2.5 as the core. This synthesis of a partial-carbon-chain dendrimer establishes a foundational step toward creating all-carbon-chain ones and may open new application avenues in material science.

Efficient and Selective Construction of 412 Metalla‐links Using Weak C−H⋅⋅⋅Halogen Interactions

AbstractThrough a coordination‐driven self‐assembly method, four metalla‐links and one tetranuclear monocycle were constructed with high selectivity and yield by adjusting the substituent species of the building blocks, as evidenced using X‐ray crystallographic analysis, electrospray ionization‐time‐of‐flight/mass spectrometry (ESI‐TOF/MS), elemental analysis and detailed solution‐state nuclear magnetic resonance (NMR) spectroscopy. Based on X‐ray crystallographic analysis and independent gradient model analysis, a significant factor leading to the formation of metalla‐links was the introduction of F, Cl, Br and I atoms, which generated additional weak C−H⋅⋅⋅X (X=F, Cl, Br and I) interactions. Furthermore, the dynamic conversion of metalla‐links to monocyclic rings in methanol solution was systematically investigated using quantitative 1H NMR techniques.

A novel integrated membrane bioreactor-stirred tank bioreactor system for simultaneous biodegradation of bisphenol A contaminated wastewater and biopolyol production: An approach towards circular bioeconomy

The present work examined the biodegradation of bisphenol A (BPA) under batch and continuous modes using hydrocarbonoclastic bacterium, Pseudomonas aeruginosa PR3. The strain showed great biodegradation potential under batch shake flask and stirred tank reactor. Bacterial growth was considerably inhibited at initial BPA concentrations > 50 mg/L. Further, membrane bioreactor (MBR) for BPA biodegradation was also evaluated under different inlet BPA concentration and hydraulic retention time (HRT) and the maximum BPA removal efficiency of 94.4 % was attained with an influent BPA concentration of 25 mg/L at 5 d of HRT. MBR also showed better performance under shock loading conditions. Identification of BPA biodegraded pathways was also performed using liquid chromatography-mass spectrometry, elucidating the different metabolites and end products formed. A subsequent enhancement in BPA removal efficieny was also observed owing to the microfiltration system of MBR that was applied to separate bacterial biomass from effluent. The maximum removal efficiency was further enhanced to 98.5 % under the same operational schedule. As the strain has the ability to produce extracellular diol synthase enzyme which transforms oleic acid into the biopolyol 7,10-dihydroxy-8(E)-octadecenoic acid, the effluent containing the enzymes was supplemented with 1 % (v/v) oleic acid under whole cell and cell-free approaches. Cell-free technique showed an enhanced bioconversion efficiency in comparison to the traditional whole cell approach. Further, the produced biopolyol was characterized using Fourier transform infrared spectroscopy, thermogravimetry, differential scanning calorimetry, and 1H nuclear magnetic resonance analyses and also depicted the antibacterial activity.