Tartaric Acid Derivatives Research Articles

Colamine and tartaric acid based innovative antioxidant and anti-spoilage food additive for fish product industry

Background: Fish farming is a vital sector of the global food industry, facing the challenge of developing efficient, chemical-free feeds for high-value fish species. To address this, innovative antimicrobials and antioxidants are crucial. This study explores the antioxidant and anti-spoilage properties of novel N-containing derivatives of natural L-tartaric acid (TA), a safe and widely used food additive. Objectives: Current research is devoted to L-tartrates’ new derivatives’ anti-spoilage and antioxidant potential as an innovative combined feed additive for fish farming. Results: TA Cyclic imide obtaining modified technology was advised. According to the obtained results, TA itself didn’t show antioxidant activity: nevertheless, in combination with new N-containing derivatives, it increased the antioxidant properties of L-ascorbic acid by about 20%. The studied TA amino-derivatives have demonstrated the emphasized activity against the fish-pathogenic Pseudomonas, Streptococcus, and other pathogenic microbes. Conclusions: TA and tartrates, in combination with new N-containing derivatives generated based on the vital compound colamine, have demonstrated several synergic antioxidant activities. They can be recommended for potential application as a cheap and effective alternative to classical anti-spoilage and preservative agents for animal feed production. Also, they showed the prolongation of feed expiration periods. It will significantly increase the quality of final fish products. A further detailed study of toxicological properties of amino derivatives is planned. Keywords: tartaric acid derivative, colamine, antimicrobial, antioxidant, anti-spoilage, feed additive

Chiroptical Properties of Semiconducting Nanoplatelets Functionalized by Tartrate Derivatives.

Inducing chirality in semiconductor nanoparticles is a recent trend motivated by the possible applications in circularly polarized light emission, spintronics, or stereoselective synthesis. However, the previous reports on CdSe nanoplatelets (NPLs) exclusively rely on cysteine or its derivatives as chiral ligands to induce optical activity. Here, we show a strong induction of chirality with derivatives of tartaric acid obtained by a single-step synthesis. The ligand exchange procedure in organic solvent was optimized for five-monolayer (5 ML) NPLs but can also be performed on 4, 3, and 2 ML. We show that the features of the CD spectra change with structural modification of the ligands and that these chiral ligands interact mainly with the first light-hole (lh1) band rather than the first heavy-hole (hh1) band, contrary to cysteine. This result suggests that chiroptical properties could be used to probe CdSe nanoplatelets' surface ligands.

Tartaric acid new derivatives as prospective and safe alternative to antimicrobials for food products packing

Introduction: Multi-drug resistance of pathogens and food spoilage bacteria is one of the most prevalent problems in contemporary science because the microbial adaptation potential is permanently being stimulated by the excessive antibiotic usage by mankind. In this research, seven new derivatives of tartaric acid (TA) were studied. Their high activity against the multi-drug resistant bacteria and the biodegradation potential by soil microflora was demonstrated.Objective: Based on multiple literature data about aldaric acids antimicrobial properties, for combating pan-drug and especially multi-drug resistant pathogenic microbes, natural L-tartaric acid was target-derivatized by cyclohexyl-, phenyl-, benzyl- and ethanolamine- functional groups into complex amino salts and cyclic imides, which have demonstrated the significant bactericidal and bacteriostatic activity against the spoilage agent bacteria, as well as phytopathogenic and human opportunistic pathogens.Results: In vitro analyses of TA ethanolamine- benzyl-, cyclohexyl- and phenyl- imides and complex amino salts have shown that the mentioned substances are highly active agents for combating multi-drug resistant Gram-positive and Gram-negative pathogens and food spoilage microbes, such as: Pseudomonas aeruginosa, Stenotrophomonas maltophilia, Klebsiella pneumonia, Salmonella enteritidis, Staphylococcus aureus, etc. These compounds are biodegradable by P. chlororaphis group non-pathogenic bacteria and their resistance is ensured by genes of nucleoid as well as are not transmitted by plasmids. In silico analyses have demonstrated their alternative mechanism of action. Conclusions: The results suggest that TA new derivatives can be potentially recommended as safe alternative antimicrobials for food packaging.Keywords: tartaric acid imides, tartaric acid complex aminosalts, spoilage microorganisms, antimicrobial activity, multi-drug resistance.

Distinct selectivity control in solar-driven bio-based α-hydroxyl acid conversion: a comparison of Pt nanoparticles and atomically dispersed Pt on CdS.

Solar-driven photocatalytic lignocellulose conversion is a promising strategy for the sustainable production of high-value chemicals, but selectivity control remains a challenging goal in this field. Here, we report efficient and selective conversion of lignocellulose-derived α-hydroxyl acids to tartaric acid derivatives, α-keto acids, and H2 using Pt-modified CdS catalysts. Pt nanoparticles on CdS selectively produce tartaric acid derivatives via C-C coupling, while atomically dispersed Pt on CdS switches product selectivity to oxidation reaction to produce α-keto acids. The atomically dispersed Pt species stabilized by Pt-S bonds promote the activation of hydroxyl group and thus switch product selectivity from tartaric acid derivatives to α-keto acids. A broad range of lignocellulose-derived α-hydroxyl acids was applied for preparing the corresponding tartaric acid derivatives and α-keto acids over the two Pt-modified CdS catalysts. This work highlights the unique performance of metal sulfides in coupling reactions and demonstrates a strategy for rationally tuning product selectivity by engineering the interaction between metal sulfide and cocatalyst.

Distinct Selectivity Control in Solar‐Driven Bio‐Based α‐Hydroxyl Acid Conversion: A Comparison of Pt Nanoparticles and Atomically Dispersed Pt on CdS

AbstractSolar‐driven photocatalytic lignocellulose conversion is a promising strategy for the sustainable production of high‐value chemicals, but selectivity control remains a challenging goal in this field. Here, we report efficient and selective conversion of lignocellulose‐derived α‐hydroxyl acids to tartaric acid derivatives, α‐keto acids, and H2 using Pt‐modified CdS catalysts. Pt nanoparticles on CdS selectively produce tartaric acid derivatives via C−C coupling, while atomically dispersed Pt on CdS switches product selectivity to the oxidation reaction to produce α‐keto acids. The atomically dispersed Pt species stabilized by Pt−S bonds promote the activation of the hydroxyl group and thus switch product selectivity from tartaric acid derivatives to α‐keto acids. A broad range of lignocellulose‐derived α‐hydroxyl acids was applied for preparing the corresponding tartaric acid derivatives and α‐keto acids over the two Pt‐modified CdS catalysts. This work highlights the unique performance of metal sulfides in coupling reactions and demonstrates a strategy for rationally tuning product selectivity by engineering the interaction between metal sulfide and cocatalyst.

A Bio-Guided Screening for Antioxidant, Anti-Inflammatory and Hypolipidemic Potential Supported by Non-Targeted Metabolomic Analysis of Crepis spp.

This study was designed to evaluate the chemical fingerprints and the antioxidant, anti-inflammatory and hypolipidemic activity of selected Crepis species collected in Greece, namely, C. commutata, C. dioscoridis, C. foetida, C. heldreichiana, C. incana, C. rubra, and Phitosia crocifolia (formerly known as Crepis crocifolia). For the phytochemical analyses, sample measurements were carried out by using nuclear magnetic resonance (NMR) spectroscopy and liquid chromatography coupled with mass spectrometry (LC-MS). Τhe extracts were evaluated both in vitro (radical scavenging activity: DPPH assay and total phenolic content: Folin–Ciocalteu) and in vivo (paw edema reduction and hypolipidemic activity: experimental mouse protocols). Among the tested extracts, C. incana presented the highest gallic acid equivalents (GAE) (0.0834 mg/mL) and the highest antioxidant activity (IC50 = 0.07 mg/mL) in vitro, as well as the highest anti-inflammatory activity with 32% edema reduction in vivo. Moreover, in the hypolipidemic protocol, the same extract increased plasma total antioxidant capacity (TAC) by 48.7%, and decreased cholesterol (41.3%) as well as triglycerides (37.2%). According to fractionation of the extract and the phytochemical results, this biological effect may be associated with the rich phenolic composition; caffeoyl tartaric acid derivatives (cichoric and caftaric acid) are regarded as the most prominent bioactive specialized metabolites. The present study contributes to the knowledge regarding the phytochemical and pharmacological profile of Crepis spp.

Total Synthesis and Functional Evaluation of IORs, Sulfonolipid‐based Inhibitors of Cell Differentiation in Salpingoeca rosetta

AbstractThe choanoflagellate Salpingoeca rosetta is an important model system to study the evolution of multicellularity. In this study we developed a new, modular, and scalable synthesis of sulfonolipid IOR‐1A (six steps, 27 % overall yield), which acts as bacterial inhibitor of rosette formation in S. rosetta. The synthesis features a decarboxylative cross‐coupling reaction of a sulfonic acid‐containing tartaric acid derivative with alkyl zinc reagents. Synthesis of 15 modified IOR‐1A derivatives, including fluorescent and photoaffinity‐based probes, allowed quantification of IOR‐1A, localization studies within S. rosetta cells, and evaluation of structure‐activity relations. In a proof of concept study, an inhibitory bifunctional probe was employed in proteomic profiling studies, which allowed to deduce binding partners in bacteria and S. rosetta. These results showcase the power of synthetic chemistry to decipher the biochemical basis of cell differentiation processes within S. rosetta.

Total Synthesis and Functional Evaluation of IORs, Sulfonolipid-based Inhibitors of Cell Differentiation in Salpingoeca rosetta.

The choanoflagellate Salpingoeca rosetta is an important model system to study the evolution of multicellularity. In this study we developed a new, modular, and scalable synthesis of sulfonolipid IOR-1A (six steps, 27 % overall yield), which acts as bacterial inhibitor of rosette formation in S. rosetta. The synthesis features a decarboxylative cross-coupling reaction of a sulfonic acid-containing tartaric acid derivative with alkyl zinc reagents. Synthesis of 15 modified IOR-1A derivatives, including fluorescent and photoaffinity-based probes, allowed quantification of IOR-1A, localization studies within S. rosetta cells, and evaluation of structure-activity relations. In a proof of concept study, an inhibitory bifunctional probe was employed in proteomic profiling studies, which allowed to deduce binding partners in bacteria and S. rosetta. These results showcase the power of synthetic chemistry to decipher the biochemical basis of cell differentiation processes within S. rosetta.

Chirality Induction on a Coordination Capsule for Circularly Polarized Luminescence.

By utilizing a confined space inside a coordination capsule consisting of achiral components, we achieve trimeric structures composed of acetic acid and 2,3-disubstituted tartaric acid derivatives. Steric and electronic interactions between the substituents on the tartaric acid and 2,2'-bipyridyl arms of the capsule permit the transfer of the chirality of the tartaric acid to the capsule, resulting in diastereoenrichment of the host-guest complexes of up to 92 % de. The chiral templates can be washed away with diethyl ether, leaving an enantiomerically enriched capsule. The resulting capsule biases the dynamic axial chirality of a 4,4'-diacetoxybiphenyl guest carrying benzothiadiazole units, demonstrating guest-to-capsule and capsule-to-guest chirality transfer. The induced chirality on the bound guest enables it to emit circularly polarized luminescence in the NIR region, demonstrating the application of induced chirality for confined spaces for the generation of chiroptical properties.

Chirality Induction on a Coordination Capsule for Circularly Polarized Luminescence

AbstractBy utilizing a confined space inside a coordination capsule consisting of achiral components, we achieve trimeric structures composed of acetic acid and 2,3‐disubstituted tartaric acid derivatives. Steric and electronic interactions between the substituents on the tartaric acid and 2,2′‐bipyridyl arms of the capsule permit the transfer of the chirality of the tartaric acid to the capsule, resulting in diastereoenrichment of the host‐guest complexes of up to 92 % de. The chiral templates can be washed away with diethyl ether, leaving an enantiomerically enriched capsule. The resulting capsule biases the dynamic axial chirality of a 4,4′‐diacetoxybiphenyl guest carrying benzothiadiazole units, demonstrating guest‐to‐capsule and capsule‐to‐guest chirality transfer. The induced chirality on the bound guest enables it to emit circularly polarized luminescence in the NIR region, demonstrating the application of induced chirality for confined spaces for the generation of chiroptical properties.

Thermodynamic and Molecular Recognition Mechanism of Diastereomeric Salt/Cocrystal-Induced Chiral Separation

To better understand the thermodynamics and molecular self-assembly mechanism of diastereomeric salt/cocrystal-induced chiral separation, a series of 1:1 cocrystals and salts consisting of chiral valines (VAL) and tartaric acid derivatives were synthesized via different methods. Powders of these as-screened cocrystals/salts were characterized by PXRD, TGA, DSC, FT-IR, and Raman spectroscopy. The crystal structures of the five cocrystals/salts were determined and analyzed. It was found that both DBTA and DTTA form diastereomeric salt pairs with VAL enantiomers. Interestingly, l-DMTA cocrystallizes with d-VAL and l-VAL via hydrogen bonding and proton transfer, respectively. Considering this particularity, the differential isothermal (10 °C) ternary phase diagrams (TPDs) of d-DMTA and l-VAL (d-VAL) cocrystals (salt) were constructed in the mixed solvent of MeOH/H2O. Moreover, a pure l-VAL:d-DMTA cocrystal and d-VAL:d-DMTA:0.5CH4O:0.25H2O salt were prepared via equimolar slurry conversion at 10 °C. In situ Raman spectroscopy was applied to monitor the molecular assembly process during the incubation of the cocrystal/salt. Molecular dynamics simulation was employed to rationalize the molecular recognition mechanism, demonstrating the excellent chirality preference of l-DMTA toward l-VAL instead of d-VAL. Calculations of density functional theory approved the synergistic instead of antagonistic effects of binding energy and solvation free energy toward chiral separation.

Optical Resolution of Two Pharmaceutical Bases with Various Uses of Tartaric Acid Derivatives and Their Sodium Salts: Racemic Ephedrine and Chloramphenicol Base.

The optically active dibenzoyltartaric acid, tartaric acid, and its sodium salts were successfully applied to the optical resolution of (1R,2S)(1S,2R)-2-(methylamino)-1-phenylpropan-1-ol (EPH) and (1R,2R)(1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol (AD) as resolving agents. It was observed that both compounds’ resolution using a mixture of salts of quasi-racemic resolving agents showed a change in chiral recognition under the same conditions compared to the result of the use of the single enantiomeric resolving agent. The changes are followed by detailed analytical (XRD, FTIR, and DSC) studies. Meanwhile, the DASH indexing software package was also tested on powder XRD patterns of pure initial materials and intermediate salt samples of high diastereomeric excess.

Chiral Assembly and Recognition of Seven Copper (II) Coordination Polymers from Tartaric Acid Derivative Ligands.

A pair of enantiomeric ligands, (2R,3R)-dibenzyl-2,3-bis(isonicotinoyloxy)succinate ((R,R)-L) and (2S,3S)-dibenzyl-2,3-bis(isonicotinoyloxy)succinate ((S,S)-L), are designed and synthesized. Seven copper (II) coordination polymers {[Cu((R,R)-L)Br2 (THF)] ⋅ CH3 CN} n (1 a) and {[Cu((S,S)-L)Br2 (THF)] ⋅ CH3 CN}n (1 b), {[Cu((R,R)-L)Cl2 (THF)] ⋅ CH3 CN}n (2 a) and {[Cu((S,S)-L)Cl2 (THF)] ⋅ CH3 CN}n (2 b), {[Cu((R,R)-L)(NO3 )2 (CH3 CN)]}n (3 a) and {[Cu((S,S)-L)(NO3 )2 (CH3 CN)]}n (3 b), {[Cu((R,R)-L)2 (CH3 CN)2 ](ClO4 )2 ⋅ 3CH3 CN}n (4) were obtained through the assemblies with CuBr2 , CuCl2 ⋅ 2H2 O, Cu(NO3 )2 ⋅ 3H2 O, Cu(ClO4 )2 ⋅ 6H2 O, respectively. Single-crystal X-ray diffraction and circular dichroism analysis demonstrate that 1 a-3 a, 1 b-3 b have a mono chiral one-dimensional (1D) chain-like spiral structure, while 4 have 1D chain-like structure whose metal centers have chiral propeller coordination environment. Ligand structure, anions and solvent systems have a regulatory effect on the formation of chiral helical structure. Further investigation has proved that 1 a can be used as circular dichroism spectrum probe for monitoring L-/D-cysteine and L-/D-penicillamine configuration and concentration in aqueous media based on ligand interchange mechanism.

APPLICATION OF TARTARIC ACID DERIVATIVES IN ENANTIOSEPARATION OF RS-IBUPROFEN

A novel Tartaric acid derivative-based chiral resolving agent has been discovered for the enantiosepration of racemic Ibuprofen [(RS)-2-(4-(2-methyl propyl) phenyl) propanoic acid]. The processinvolves optimization of diastereomeric salt formed between (+) Ibuprofen and optically pure tartaric acid derivatives, followed by separating the individual enantiomer by acid salt preparation. Characterization of the synthesized compound has been carried out by elemental analysis, melting point, FT-IR, UV, HPLC, and 1H NMR spectra. The developed separation method is simple, cost-effective, and industrially viable.

Preparation of eco-friendly nanocomposites based on immobilization of magnetic activated carbon with tartaric acid: Application for adsorption of heavy metals and evaluation of their catalytic activity in C-C coupling reaction

A novel adsorbent containing bio-nanocomposites of activated carbon merged with magnetic nanoparticles was prepared and its surface was modified with tartaric acid derivative (TAR@MAC NCs). The TAR@MAC NCs adsorbent was evaluated for its ability to adsorption process for Cr, Co and Pb heavy metals. The various parameters such as amount adsorbent, concentration of heavy metals, contact time and pH value was studied using the response surface methodology (RSM) based on the central composite design (CCD). The adsorption process was conformed by the isotherm of Langmuir model and kinetic model of pseudo-second-order. Through the Langmuir isotherm model, the maximum adsorption capacity of TAR@MAC NCs for Cr, Pb and Co ions reached 86.55, 83.30 and 83.72 mg g−1, respectively. In the continuation of this project, with loading of Pd NPs onto the nanocomposite, the Pd-TAR@MAC NCs catalyst was synthesized and was studied for the Suzuki–Miyaura coupling reaction of aryl halides and phenyl boronic acid under green condition. The nanocomposites exhibited good reusability (5 times) and was separated easily from an aqueous solution with an external magnet.

A Modular Approach to the Antifungal Sphingofungin Family: Concise Total Synthesis of Sphingofungin A and C.

Sphingofungins are fungal natural products known to inhibit the biosynthesis of sphingolipids which play pivotal roles in various cell functions. Here, we report a short and flexible synthetic approach towards the sphingofungin family. Key step of the synthesis was a decarboxylative cross‐coupling reaction of chiral sulfinyl imines with a functionalized tartaric acid derivative, which yielded the core motif of sphingofungins carrying four consecutive stereocenters and a terminal double bond. Subsequent metathesis reaction allowed for the introduction of different side chains of choice resulting in a total of eight sphingofungins, including for the first time sphingofungin C (eight steps from commercially available protected tartaric acid with an overall yield of 6 %) and sphingofungin A (ten steps). All newly synthesized derivatives were tested for their antifungal, cell‐proliferative and antiparasitic activity unraveling their structure–activity relations.

A Modular Approach to the Antifungal Sphingofungin Family: Concise Total Synthesis of Sphingofungin A and C

AbstractSphingofungins are fungal natural products known to inhibit the biosynthesis of sphingolipids which play pivotal roles in various cell functions. Here, we report a short and flexible synthetic approach towards the sphingofungin family. Key step of the synthesis was a decarboxylative cross‐coupling reaction of chiral sulfinyl imines with a functionalized tartaric acid derivative, which yielded the core motif of sphingofungins carrying four consecutive stereocenters and a terminal double bond. Subsequent metathesis reaction allowed for the introduction of different side chains of choice resulting in a total of eight sphingofungins, including for the first time sphingofungin C (eight steps from commercially available protected tartaric acid with an overall yield of 6 %) and sphingofungin A (ten steps). All newly synthesized derivatives were tested for their antifungal, cell‐proliferative and antiparasitic activity unraveling their structure–activity relations.

First use of grape waste-derived building blocks to yield antimicrobial materials

Grape marc is an underutilised waste material that poses significant environmental issues. This study offers the first proof-of-concept investigation into the polymerisation of both crude and purified Sauvignon blanc grape marc extracts using the diacyl chlorides terephthaloyl chloride, succinyl chloride, adipoyl chloride, sebacoyl chloride, and the tartaric acid derivative (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarbonyl dichloride to obtain new materials, in what to the best of our knowledge is the first reported example of a direct polymerisation of an agricultural waste extract. A total of 26 novel materials were prepared. It has also shown that quercetin, a phenolic monomer found in grape marc extracts, can be polymerised with (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarbonyl dichloride to give a polymer that shows activity towards S. aureus.

Helical Structures of Nylon-Like Oligomers Consisting of 1,2-Diamine and 1,2-Dicarboxylic Acid Building Blocks Containing a Five-Membered Ring Constraint.

A series of nylon-like oligomers was synthesized, which consisted of alternating cyclic 1,2-diamine and 1,2-dicarboxylic acid building blocks with a five-membered ring constraint. The nylon 2 4 oligomers are symmetric and display helical structures similar to the β-peptide 12-helix with intramolecular 12-membered ring hydrogen bonds. The cyclopentane moiety allows each building block to promote 12-helical folding. In addition, a tartaric acid derivative with the acetonide moiety increases the solubility of oligomers in common organic solvents and promotes helical folding.

Multi-isotope Analysis of Tartaric Acid Derivative: Potassium Bitartrate

Multi-isotope Analysis of Tartaric Acid Derivative: Potassium Bitartrate