Highly selective synthesis of d-amino acids from readily available l-amino acids by a one-pot biocatalytic stereoinversion cascade

d-Amino acids are key intermediates required for the synthesis of important pharmaceuticals. However, establishing a universal enzymatic method for the general synthesis of d-amino acids from cheap and readily available precursors with few by-products is challenging. In this study, we constructed and optimized a cascade enzymatic route involving l-amino acid deaminase and d-amino acid dehydrogenase for the biocatalytic stereoinversions of l-amino acids into d-amino acids. Using l-phenylalanine (l-Phe) as a model substrate, this artificial biocatalytic cascade stereoinversion route first deaminates l-Phe to phenylpyruvic acid (PPA) through catalysis involving recombinant Escherichia coli cells that express l-amino acid deaminase from Proteus mirabilis (PmLAAD), followed by stereoselective reductive amination with recombinant meso-diaminopimelate dehydrogenase from Symbiobacterium thermophilum (StDAPDH) to produce d-phenylalanine (d-Phe). By incorporating a formate dehydrogenase-based NADPH-recycling system, d-Phe was obtained in quantitative yield with an enantiomeric excess greater than 99%. In addition, the cascade reaction system was also used to stereoinvert a variety of aromatic and aliphatic l-amino acids to the corresponding d-amino acids by combining the PmLAAD whole-cell biocatalyst with the StDAPDH variant. Hence, this method represents a concise and efficient route for the asymmetric synthesis of d-amino acids from the corresponding l-amino acids.

An efficient one-pot biocatalytic cascade was developed for synthesis of d-amino acids from readily available l-amino acids via stereoinversion.     

Formal synthesis of (+)-lactacystin from l-serine

A formal, stereocontrolled synthesis of lactacystin has been completed from t-Bu-O-l-serine, providing the key intermediate 13, also useful for the generation of a range of C-9 analogues.

A formal, stereocontrolled synthesis of lactacystin has been completed from t-Bu-O-l-serine.     

Computational study on the polymerization reaction of d-aminopeptidase for the synthesis of d-peptides

Almost all natural proteins are composed exclusively of l-amino acids, and this chirality influences their properties, functions, and selectivity. Proteases can recognize proteins composed of l-amino acids but display lower selectivity for their stereoisomers, d-amino acids. Taking this as an advantage, d-amino acids can be used to develop polypeptides or biobased materials with higher biostability. Chemoenzymatic peptide synthesis is a technique that uses proteases as biocatalysts to synthesize polypeptides, and d-stereospecific proteases can be used to synthesize polypeptides incorporating d-amino acids. However, engineered proteases with modified catalytic activities are required to allow the incorporation of d-amino acids with increased efficiency. To understand the stereospecificity presented by proteases and their involvement in polymerization reactions, we studied d-aminopeptidase. This enzyme displays the ability to efficiently synthesize poly d-alanine-based peptides under mild conditions. To elucidate the mechanisms involved in the unique specificity of d-aminopeptidase, we performed quantum mechanics/molecular mechanics simulations of its polymerization reaction and determined the energy barriers presented by the chiral substrates. The enzyme faces higher activation barriers for the acylation and aminolysis reactions with the l-stereoisomer than with the d-substrate (10.7 and 17.7 kcal mol⁻¹ higher, respectively). The simulation results suggest that changes in the interaction of the substrate with Asn155 influence the stereospecificity of the polymerization reaction.

We studied the molecular mechanism of d-aminopeptidase for the synthesis of polypeptides incorporating d-amino acids.     

Chemoenzymatic synthesis of polypeptides in neat 1,1,1,2-tetrafluoroethane solvent

Chemoenzymatic polypeptide synthesis offers several advantages over chemical or other biological routes, however, the use of aqueous-based media suffers from reverse hydrolysis reactions that challenge peptide chain propagation. Herein, the protease from subtilisin Carlsberg biocatalyzed the synthesis of poly-l-PheOEt, poly-l-LeuOEt, and the copolymers poly-l-PheOEt-co-l-LeuOEt from their amino acid ethyl ester substrates in a neat liquid 1,1,1,2-tetrafluoroethane solvent. The products, achieved in acceptable yields (ca. 50%), were fully characterized showing relatively high molar mass (ca. 20 000 Da for poly-l-PheOEt). This non-toxic low-boiling hydrofluorocarbon enhances enzymatic peptide propagation by limiting hydrolysis owing to its hydrophobic and relatively polar characteristics that sustain the protease activity and solubilize substrates and products. Computational molecular dynamic calculations were used to assess the l-PheOEt/l-LeuOEt-solvent and polypeptide-solvent interactions in this system. Additionally, the homopolypeptides displayed higher crystallinity than the copolypeptides with random incorporation of amino acid ethyl esters, notwithstanding the significantly highest specificity for Phe in this system. Interestingly, secondary structure characterization of the products by FTIR and circular dichroism suggests a non-common peptide folding.

Chemoenzymatic polypeptide synthesis offers several advantages over chemical or other biological routes, however, the use of aqueous-based media suffers from reverse hydrolysis reactions that challenge peptide chain propagation.     

Mechanistic study on substitution reaction of a citrato(p-cymene)Ru(ii) complex with sulfur-containing amino acids

The reactions of a dichloro(p-cymene)ruthenium(ii) dimer, [RuCl₂(p-cymene)]₂, with citric acid and sulfur-containing amino acids gave only [Ru(L)(p-cymene)]-type complexes (L = citrate (Cit), l-penicillaminate (l-Pen), S-methyl-l-cysteinate (S-Me-l-Cys) and l-methioninate (l-Met)) in aqueous solutions at various pHs and molar ratios of the reactants, where Cit and the amino acids act as a tridentate ligand. These sulfur-containing amino acid complexes with bound nitrogen, oxygen and sulfur atoms and η⁶-p-cymene take S absolute configuration around Ru(ii) selectively, having the α-proton oriented in the opposite direction from the Ru(ii) center. The concentration dependences of the observed pseudo-first-order rate constants were provided for the substitution reactions of the citrato complex, [Ru(Cit)(p-cymene)], with a large excess of the sulfur-containing amino acids at various temperatures at pH 7.3, where solvolysis path was observed for S-Me-l-Cys and l-Met as an intercept but not for l-Pen. The activation parameters for the substitution reactions by the direct attack of the amino acids were changed significantly, indicating that the reaction mechanism varies sensitively with the amino acids from an associative mechanism to an interchange one. The pH dependences of the rate constants of the substitution reactions suggest that the carboxylate group is an attacking group for S-Me-l-Cys and l-Met under neutral conditions and the thiol group of l-Pen acts as an entering group constantly at any pH showing a considerably smaller activation energy compared with S-Me-l-Cys and l-Met. Differences in stabilities of the amino acid complexes were obtained from the equilibrium constants for the substitution reactions between the amino acids. These results indicate that the activation energies for the substitution reactions of the citrato complex with the amino acids are moderately correlated with the stabilities of the formed amino acid complexes.

Thorough kinetic study revealed characteristics of the reaction mechanism for arene ruthenium(ii) complexes with bio-related ligands.     

A novel surface plasmon resonance sensor based on a functionalized graphene oxide/molecular-imprinted polymer composite for chiral recognition of l-tryptophan

Herein, a novel surface plasmon resonance (SPR) sensor based on a functionalized graphene oxide (GO)/molecular-imprinted polymer composite was developed for the chiral recognition of l-tryptophan (l-Trp). The composite''s recognition element was prepared via a facile and green synthesis approach using polydopamine as both a reducer of GO and a functional monomer as well as a cross-linker for molecular imprinting. The composite was characterized via Fourier transform infrared spectroscopy, scanning electron microscopy, X-ray diffraction, and Raman spectroscopy. After attaching the composite onto the gold surface of an SPR chip, the sensor was characterized using contact-angle measurements. The sensor exhibited excellent selectivity and chiral recognition for the template (i.e., l-Trp). Density functional theory computations showed that the difference in hydrogen bonding between the composite element and l-Trp and d-Trp played an important role in chiral recognition.

Novel SPR sensor for chiral recognition of l-tryptophan using a functionalized graphene oxide/molecularly-imprinted polymer composite as a recognition element.     

Synthesis and stereocomplex formation of enantiomeric alternating copolymers with two types of chiral centers,poly(lactic acid-alt-2-hydroxybutanoic acid)s

Stereocomplex (SC) formation was reported for the first time for enantiomeric alternating copolymers consisting of repeating units with two types of chiral centers, poly(lactic acid-alt-2-hydroxybutanoic acid)s [P(LA-alt-2HB)s]. l,l-Configured poly(l-lactic acid-alt-l-2-hydroxybutanoic acid) [P(LLA-alt-l-2HB)] and d,d-configured poly(d-lactic acid-alt-d-2-hydroxybutanoic acid) [P(DLA-alt-d-2HB)] were amorphous. Blends of P(LLA-alt-l-2HB) and P(DLA-alt-d-2HB) were crystallizable and showed typical SC-type wide-angle X-ray diffraction profiles similar to those reported for stereocomplexed blends of poly(l-lactic acid) and poly(d-lactic acid) homopolymers and of poly(l-2-hydroxybutanoic acid) and poly(d-2-hydroxybutanoic acid) homopolymers, and of l,l-configured poly(l-lactic acid-co-l-2-hydroxybutanoic acid) [P(LLA-co-l-2HB)] and d,d-configured poly(d-lactic acid-co-d-2-hydroxybutanoic acid) [P(DLA-co-d-2HB)] random copolymers. The melting temperature values and melting enthalpy values at 100% crystallinity for stereocomplexed solvent-evaporated and precipitated P(LLA-alt-l-2HB)/P(DLA-alt-d-2HB) blends were correspondingly 187.5 and 187.9 °C, and 98.1 and 91.8 J g⁻¹. Enantiomeric polymer blending of P(LLA-alt-l-2HB) and P(DLA-alt-d-2HB) can confer crystallizability by stereocomplexation and the biodegradable materials with a wide variety of physical properties and biodegradability are highly expected to be prepared by synthesis of alternating copolymers of various combinations of two types of chiral α-substituted 2-hydroxyalkanoic acid monomers and their SC crystallization.

Stereocomplex formation was reported for alternating copolymers of chiral α-substituted 2-hydroxyalkanoic acids which can be utilized for preparation of biodegradable materials with a variety of physical properties and biodegradability.     

Novel Schiff base cobalt(ii) phthalocyanine with appliance of MWCNTs on GCE: enhanced electrocatalytic activity behaviour of α-amino acids

A novel tetra-4-{(E)-[(8-aminonaphthalen-1-yl)imino]methyl}-2-methoxyphenol Co(ii) phthalocyanine (CoTANImMMPPc) was synthesized using a precursor protocol and characterized via electroanalytical and spectroscopic techniques. The FT-IR spectra of the synthesized compounds showed significant peaks corresponding to the functional groups of the precursors and phthalocyanine (Pc) compound. The mass and NMR spectra confirmed the formation of the target precursor compounds. A film of CoTANImMMPPc was deposited on the surface of an electrode and applied for the detection and monitoring of l-alanine and l-arginine. The cyclic voltammetric studies of l-alanine and l-arginine using the (CoTANImMMPPc/MWCNTs/GC) electrode showed a linear response in the range of 50–500 nM and the limit of detection was found to be 1.5 and 1.2 nM, respectively. Differential pulse voltammetry and chronoamperometry showed that the catalytic response for l-alanine and l-arginine is in the range of 50–500 nM with an LoD of 1.8 and 2.3 nM, respectively. The oxidation-active CoTANImMMPPc film significantly enhanced the current response in the chronoamperometric method and displayed a selective and sensitive response towards l-alanine and l-arginine in the presence of various other bio-molecules. The developed electrode showed good working stability and was applied for the analysis of real samples, which yielded satisfactory results. Therefore, CoTANImMMPPc-MWCNTs/GCE shows good analytical performance, is economical and produced via a simple synthetic method and can be applied as a sensor for the detection of l-alanine and l-arginine.

A novel CoTANImMMPPc complex was synthesized using a precursor protocol and characterized via electroanalytical and spectroscopic techniques with enhanced electrocatalytic behaviour of α-amino acids.     

Industrial kinetic resolution of d,l-pantolactone by an immobilized whole-cell biocatalyst

Immobilized whole-cells of Pichia pastoris harboring recombinant d-lactonase were entrapped in calcium alginate gels and used as an efficient biocatalyst for catalytic kinetic resolution of d,l-pantolactone. The immobilized whole-cell biocatalyst exhibited good catalytic stability, which was applied for stereospecific hydrolysis of d-pantolactone for up to 56 repeated batch reactions without obvious loss in the catalytic activity and enantioselectivity.

Immobilized whole-cells of Pichia pastoris harboring recombinant d-lactonase were entrapped in calcium alginate gels and used as an efficient biocatalyst for catalytic kinetic resolution of d,l-pantolactone.     

Anticyanobacterial effect of l-lysine on Microcystis aeruginosa

Cyanobacterial blooms can cause serious environmental problems and threaten aquatic organisms and human health. It is therefore essential to effectively control cyanobacterial blooms in aquatic ecosystems. In the present study, the anticyanobacterial effect of l-lysine on Microcystis aeruginosa was examined. The results showed that the growth of M. aeruginosa (>90%) was effectively inhibited by l-lysine at dosages of 5.0, 6.5, and 8.0 mg L⁻¹ after 3 d treatment. The content of superoxide anion radicals, MDA content and SOD activity in M. aeruginosa cells increased after 1 d of treatment with l-lysine (3.0, 5.0, 6.5, and 8.0 mg L⁻¹), revealing that l-lysine induced oxidative stress in the cyanobacterial cells. The chlorophyll-a and protein contents in M. aeruginosa treated with l-lysine (3.0, 5.0, 6.5, and 8.0 mg L⁻¹) decreased after 2 d, indicating damage of the photosynthetic system by l-lysine treatment. Additionally, the production of exopolysaccharide by M. aeruginosa also increased and the expression of polysaccharide synthesis genes was upregulated by 3.0 mg L⁻¹l-lysine after 3 d of treatment. In response to the algicidal effects of l-Lysine, M. aeruginosa upregulated exopolysaccharide synthesis. Electron microscopic observations demonstrated that the cell membrane of M. aeruginosa was broken down during treatment with l-lysine (≥3.0 mg L⁻¹). Our results revealed that the effects of l-lysine on M. aeruginosa cells were comprehensive, and l-lysine is therefore an efficient anticyanobacterial reagent.

l-lysine had an anticyanobacterial effect on Microcystis aeruginosa, which involved growth inhibition, physiological and metabolic disturbance, and cell membrane damage.     

Synthesis and solvent-controlled self-assembly of diketopiperazine-based polyamides from aspartame

An aspartame-based AB-type diketopiperazine monomer, cyclo(l-aspartyl-4-amino-l-phenylalanyl) (ADKP), was synthesized and subsequently utilized in the polycondensation of homo-polyamides with high molecular weights. By using various amino acids, dicarboxylic acids, and diamines, random DKP-based copolymers were also synthesized. The self-assembly properties of ADKP and poly(cyclo(l-aspartyl-4-amino-l-phenylalanyl)) (PA1) were studied via the solvent displacement method. Notably, PA1 self-assembled into particles with various morphologies in different solvent systems, such as irregular networks, ellipsoids, and hollow particles. The morphological transformation was also confirmed by dropping acetone and toluene onto the PA1 particles. Furthermore, infrared spectra and Hansen solubility parameters of PA1 and different solvents revealed the particle formation mechanism, which provided more insights into the relationship between the morphology and strength of the hydrogen bonding of each solvent.

Diketopiperazine-based polyamides have been synthesized from aspartame, and could self-assemble into particles with various morphologies in different solvents.     

Investigation on the chirality mechanism of chiral carbon quantum dots derived from tryptophan

Chiral carbon quantum dots (CQDs) with chirality, fluorescence and biocompatibility were synthesized by a one-step method with l-/d-tryptophan (l-/d-Trp), as both carbon source and chiral source. Levogyration-/dextrorotation-CQDs (l-/d-CQDs) were characterized by transmission electron microscopy, Fourier transform infrared spectrometry, ultraviolet-visible absorption, excitation and emission spectrometry and circular dichroism (CD) spectrometry. Results show that l-CQDs and d-CQDs present similar spherical morphology, functional groups and optical properties. The CD signal, around 220, 240 and 290 nm are opposite and symmetric, which conclusively demonstrates that l-CQDs and d-CQDs are enantiomers. Besides the CD signal around 220 nm from the inheritance of l-/d-Trp, two new chiral signals around 240 and 290 nm were induced by chiral environment.

To clarify the chirality mechanism of chiral CQDs prepared by l-/d-tryptophan, the chirality origin in CQD structure was revealed.     

Copper-catalyzed C–S direct cross-coupling of thiols with 5-arylpenta-2,4-dienoic acid ethyl ester

A selective copper (Cu)-catalyzed C–S bond direct cross-coupling of thiols with 5-arylpenta-2,4-dienoic acid ethyl ester was developed. Notably, various biologically active 5-phenyl-3-phenylsulfanylpenta-2,4-dienoic acid ethyl ester derivatives were efficiently synthesized under moderate conditions. Finally, a plausible Cu(i)/Cu(iii) reaction mechanism was proposed.

A selective copper (Cu)-catalyzed C–S bond direct cross-coupling of thiols with 5-arylpenta-2,4-dienoic acid ethyl ester was developed.     

Synthesis of indazoles from 2-formylphenylboronic acids

A method for the synthesis of indazoles was developed which involves a copper(ii) acetate catalysed reaction of 2-formylboronic acids with diazadicaboxylates followed by acid or base induced ring closure. Hydrazine dicarboxylates were also shown as competent reaction partners for the synthesis of indazoles, however, they required a stoichiometric amount of copper(ii) acetate for the C–N bond formation step. The transformation can be efficiently performed as a two step-one pot procedure to give a range of 1N-alkoxycarbonyl indazoles.

A method for the synthesis of indazoles was developed which involves a copper(ii) acetate catalysed reaction of 2-formylboronic acids with diazadicaboxylates followed by acid or base induced ring closure.     

Tuning residual chirality in carbon dots with anti-microbial properties

Chirality remains a critical consideration in drug development and design, as well as in applications of enantioselective recognition and sensing. However, the preparation of chiral nanomaterials requires extensive post synthetic modifications with a chiral agent, coupled with extensive purification. This limits the use and application of chiral nanomaterials. Herein, we report a facile, one-step microwave-assisted synthesis of chiral carbon dots through the reaction of l- and d-cysteine amino acid precursors and citric acid. We modulated the synthetic parameters to preserve and tune the residual chiral properties of the dots and demonstrate that the reaction conditions play a critical role in dictating the chiral behaviour of the dots. Finally, in a proof of concept application we demonstrated that the synthesized carbon dots, particularly d-carbon dots inhibit bacterial growth at a lower concentration than l-carbon dots. By varying bacterial strains and chirality of the carbon dots, concentrations ranging from 0.25–4 mg mL⁻¹ of the nanoparticles were required to inhibit microbial growth. The ability to preserve and tune chirality during synthesis can open up novel avenues and research directions for the development of enantioselective materials, as well as antibacterial films and surfaces.

Chiral carbon dots, prepared from the unnatural d-enantiomer of cysteine, inhibit the growth of Escherichia coli ATCC 25922 and MG1655 at a lower concentration than l-carbon dots, prepared from the l-enantiomer.     

Remarkable diastereomeric effect on thermoresponsive behavior of polyurethane based on lysine and tartrate ester derivatives

This study describes the long-distance diastereomeric effect on thermoresponsive properties in water-soluble diastereomeric polyurethanes (PUs) composed of an l-lysine ethyl ester diisocyanate and a trimethylene glycol l-/d-tartrate ester, which have differences in spatial arrangements of the ethyl esters in the mirror image. The PUs based on l-lysine and l-/d-tartrate ester, named l-PU and d-PU, were synthesized with various number average molecular weights from 4700 to 13 100. In turbidimetry, l-PU showed a steep phase transition from 100%T to 0%T within about 10 °C at 4 g L⁻¹, whereas d-PU did not change completely to 0%T transmittance even at 80 °C at 4 g L⁻¹. In addition, the thermoresponsive properties of l-PU were less affected by concentration than those of d-PU. This long-distance diastereomeric effect on thermoresponsive behavior between l-PU and d-PU appeared in common among 6 samples with 4700 to 13 100 number average molecular weight. In the dynamic light scattering experiments at each transmittance, the hydrodynamic diameter (D_h) of l-PU increased up to 1000 nm, while the D_h of d-PU remained almost at 200–300 nm. The C O stretching vibration of FT-IR spectra showed that d-PU has more hydrogen-bonded ester groups than L-PU. Thus, we speculated that the difference in the retention of polymer chains in the micelle to promote intermicellar bridging generates the long-distance diastereomeric effect.

The long-distance diastereomeric effect on thermoresponsive properties in a polyurethane system consisting of chiral monomers was reported.     

Study of hydrogen explosion control measures by using l-phenylalanine for aluminum wet dust removal systems

Wet dust removal systems are an effective design for preventing aluminum dust explosion in the process of metal polishing. However, wet dust removal systems pose hydrogen fire and explosion risks because aluminum dust can react with water to produce hydrogen gas. According to previous studies, l-phenylalanine can be used to solve the corrosion problem of metal slabs. In this work, a hydrogen inhibition method was proposed to inhibit hydrogen production in wet dust removal systems by using l-phenylalanine. The hydrogen evolution curves of aluminum particles reacting with different concentrations of l-phenylalanine solutions obtained via hydrogen inhibition experiments revealed that when the concentration of l-phenylalanine solutions reached 20 g L⁻¹, essentially no hydrogen gas was produced. Scanning electron microscopy (SEM) and energy dispersive spectroscopy (EDS) were used to characterize the aluminum particles before and after the reaction. This work shows that l-phenylalanine is a good inhibitor. The adsorption of l-phenylalanine on the aluminum particle surface obeys the Langmuir adsorption isotherm. Additionally, Fourier transform infrared (FTIR) analysis was conducted to explain the physicochemical mechanism of the l-phenylalanine inhibition of hydrogen production. l-Phenylalanine is an environmentally friendly inhibitor and hence can be used in wet dust removal systems for the treatment of aluminum dust, which can reduce the hydrogen fire and explosion risk.

The reaction between aluminium dust and water in wet dust removal system is inhibited by using l-phenylalanine.     

l-Menthol alleviates cigarette smoke extract induced lung injury in rats by inhibiting oxidative stress and inflammation via nuclear factor kappa B,p38 MAPK and Nrf2 signalling pathways

l-Menthol is the main ingredient of peppermint which affects various pharmacological effects such as anti-inflammation and anti-oxidative activity. In this study, we aimed to evaluate the potential effects of l-menthol on cigarette smoke extract (CSE) induced lung injury in rats. Morphology assessment results revealed that administration with l-menthol (5, 10 or 20 mg kg⁻¹ d⁻¹) significantly alleviated CSE-induced lung injury. Besides, l-menthol significantly reduced the inflammatory response by suppressing the production of tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β) and interleukin-6 (IL-6) via downregulating nuclear factor kappa B (NF-κB) and p38 MAPK pathways. Meanwhile, l-menthol decreased the levels of oxidative stress markers including malondialdehyde (MDA) and myeloperoxidase (MPO) whereas it increased the amount of glutathione (GSH), glutathione peroxidase (GSH-Px), superoxide dismutase (SOD) and total antioxidant capacity (T-AOC) through activation of the Nrf2 pathway. Furthermore, the expression of MMP-9 and TIMP-1 in lungs was reduced after treatment with l-menthol, and this indicated that l-menthol might have a potential effect on airway remodeling. Moreover, immunohistochemistry analyses indicated that l-menthol could suppress the infiltration of CD4⁺ and CD8⁺ T cells in lung tissues and this was probably due to the immune regulation activity of l-menthol. Taken together, our findings support that l-menthol might be a potential candidate for the treatment of CSE-induced lung injury in rats.

l-Menthol is the main ingredient of peppermint which affects various pharmacological effects such as anti-inflammation and anti-oxidative activity.     

Green syntheses of silver nanoparticle decorated reduced graphene oxide using l-methionine as a reducing and stabilizing agent for enhanced catalytic hydrogenation of 4-nitrophenol and antibacterial activity

Herein, we have reported a facile and green synthesis approach of Ag NP decorated reduced graphene oxide (RGO) through an in situ self-assembly method in the presence of l-methionine (l-Met) as reducing and stabilizing agent. The electronic properties, crystal structure, and morphology of the as-synthesized RGO–Ag nanocomposite were investigated by UV-Visible (UV-Vis) spectroscopy, Fourier transform-infrared (FTIR), X-ray diffraction (XRD), field emission scanning electron microscopy (FESEM) and transmission electron microscopy (TEM) techniques. UV-Vis and FTIR show the effective reduction of GO and the formation of Ag NPs using l-Met. FESEM, TEM, and XRD analysis show the successful impregnation of Ag NPs into RGO with a 23 nm average crystallite size. The RGO–Ag nanocomposite with NaBH₄ shows a fast-catalytic reduction of 4-nitrophenol (4-NP) to 4-aminophenol (4-AMP). The enhanced catalytic activity of RGO–Ag nanocomposites can be attributed to the synergistic effect of improved adsorption capacity and the absence of agglomeration of Ag nanoparticles. Moreover, RGO–Ag showed strong antibacterial activity against B. subtilis and E. coli.

Herein, we have reported a facile and green synthesis approach of Ag NP decorated reduced graphene oxide (RGO) through an in situ self-assembly method in the presence of l-methionine (l-Met) as reducing and stabilizing agent.     

l-Proline catalyzed one-pot synthesis of polysubstituted pyridine system incorporating benzothiazole moiety via sustainable sonochemical approach

The efficient, highly convenient synthesis of polysubstituted pyridine derivatives was established via the reaction of N-(benzothiazol-2-yl)-2-cyanoacetamides with an assortment of arylidene malononitriles and arylidene ethyl cyanoacetates in the presence of l-proline as an efficient organocatalyst for this type of ultrasonic-mediated Michael addition. The mechanistic pathway and factors affecting this reaction were also established. The main characteristics of this procedure are high yields, use of a cost-effective catalyst, and easy work-up and purification.

The l-proline catalyzed ultrasonic-mediated synthesis of polysubstituted pyridone derivatives through the reaction of N-(benzothiazol-2-yl)-2-cyanoacetamides with an assortment of arylidenes has demonstrated as an efficient protocol.