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call loadScript javascripts\jsmol\core\package.js call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js Jmol JavaScript applet jmolApplet0_object__283392504232329__ initializing getValue debug = null getValue logLevel = null getValue allowjavascript = null AppletRegistry.checkIn(jmolApplet0_object__283392504232329__) call loadScript javascripts\jsmol\core\corestate.z.js viewerOptions: { "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:45873","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__283392504232329__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"283392504232329","bgcolor":"#000" } (C) 2012 Jmol Development Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $ java.vendor: j2s java.version: 0.0 os.name: j2s Access: ALL memory: 0.0/0.0 processors available: 1 useCommandThread: false appletId:jmolApplet0_object (signed) starting HoverWatcher_1 getValue emulate = null defaults = "Jmol" getValue boxbgcolor = null getValue bgcolor = #000 backgroundColor = "#000" getValue ANIMFRAMECallback = null getValue APPLETREADYCallback = Jmol._readyCallback APPLETREADYCallback = "Jmol._readyCallback" getValue ATOMMOVEDCallback = null getValue CLICKCallback = null getValue ECHOCallback = null getValue ERRORCallback = null getValue EVALCallback = null getValue HOVERCallback = null getValue LOADSTRUCTCallback = null getValue MEASURECallback = null getValue MESSAGECallback = null getValue MINIMIZATIONCallback = null getValue PICKCallback = null getValue RESIZECallback = null getValue SCRIPTCallback = null getValue SYNCCallback = null getValue STRUCTUREMODIFIEDCallback = null getValue doTranslate = null language=en_US getValue popupMenu = null getValue script = null Jmol applet jmolApplet0_object__283392504232329__ ready call loadScript javascripts\jsmol\core\corescript.z.js call loadScript javascripts\jsmol\J\script\FileLoadThread.js starting QueueThread0_2 script 1 started starting HoverWatcher_3 starting HoverWatcher_4 The Resolver thinks Mol Marvin 03200800143D starting HoverWatcher_5 Time for openFile( Marvin 03200800143D 16 15 0 0 0 0 999 V2000 2.6080 0.5889 0.3249 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2396 2.3224 0.2890 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5155 1.0291 0.0599 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4622 0.1274 -0.5313 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9929 -1.1901 -0.6797 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7515 0.0861 0.3981 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3572 -0.4150 1.6760 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8048 -0.8161 -0.1917 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1790 -1.7877 0.4190 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3278 -0.5389 -1.3964 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9151 2.9011 0.6673 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1604 0.5100 -1.5057 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2466 -1.4909 0.2034 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1561 1.0918 0.5112 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0054 -1.3045 1.5312 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0036 -1.1168 -1.7751 H 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 2 3 1 0 0 0 0 2 11 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 10 16 1 0 0 0 0 M END): 20 ms reading 16 atoms ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false 1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them. Default Van der Waals type for model set to Babel 16 atoms created ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation Script completed Jmol script terminated
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| InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m0/s1 |
| FEWJPZIEWOKRBE-LWMBPPNESA-N |
| O[C@@H]([C@H](O)C(O)=O)C(O)=O |
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Escherichia coli
(NCBI:txid562)
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See:
PubMed
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Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
(via 2,3-dihydroxybutanedioic acid )
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via 2,3-dihydroxybutanedioic acid )
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View more via ChEBI Ontology
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(2S,3S)-2,3-dihydroxybutanedioic acid
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(−)-(S,S)-tartaric acid
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ChemIDplus
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(−)-D-tartaric acid
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ChemIDplus
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(−)-tartaric acid
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IUPAC
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(−)-Weinsäure
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ChEBI
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(-)-Tartaric acid
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KEGG COMPOUND
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(2S,3S)-(−)-tartaric acid
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ChemIDplus
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(2S,3S)-2,3-dihydroxysuccinic acid
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ChEBI
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(2S,3S)-tartaric acid
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IUPAC
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(S,S)-(−)-tartaric acid
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ChemIDplus
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(S,S)-tartaric acid
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KEGG COMPOUND
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D(-)-TARTARIC ACID
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PDBeChem
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D-(−)-tartaric acid
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ChemIDplus
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D-Tartaric acid
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KEGG COMPOUND
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D-threaric acid
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IUPAC
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Linksweinsäure
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ChEBI
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147-71-7
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CAS Registry Number
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ChemIDplus
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147-71-7
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CAS Registry Number
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NIST Chemistry WebBook
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1725145
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Reaxys Registry Number
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Reaxys
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4666810
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Beilstein Registry Number
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Beilstein
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50225
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Gmelin Registry Number
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Gmelin
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Ahmad Aljafree NF, Ahmad MF, Abd Aziz U, Borzehandani MY, Mohamad Jaafar A, Asib N, Nguyen HL, Mohamed Tahir MI, Mohammad Latif MA, Cordova KE, Abdul Rahman MB (2025)
Calcium l-Malate and d-Tartarate Frameworks as Adjuvants for the Sustainable Delivery of a Fungicide.
ACS applied materials & interfaces 17, 17672-17683 [PubMed:38109287]
[show Abstract]
Agrichemical adjuvants that combine a highly selective, efficient, and active mode of operation are critically needed to realize a more sustainable approach to their usage. Herein, we report the synthesis and full characterization of two new metal-organic frameworks (MOFs), termed UPMOF-1 and UPMOF-2, that were constructed from eco-friendly Ca2+ ions and naturally occurring, low-molecular weight plant acids, l-malic and d-tartaric acid, respectively. Upon structural elucidation of both MOFs, a widely used fungicide, hexaconazole (Hex), was loaded on the structures, reaching binding affinities of -5.0 and -3.5 kcal mol-1 and loading capacities of 63% and 62% for Hex@UPMOF-1 and Hex@UPMOF-2, respectively, as a result of the formation of stable host-guest interactions. Given the framework chemistry of the MOFs and their predisposition to disassembly under relevant agricultural conditions, the sustained release kinetics were determined to show nearly quantitative release (98% and 95% for Hex@UPMOF-1 and Hex@UPMOF-2, respectively) after >500 h, a release profile drastically different than the control (>80% release in 24 h), from which the high efficiency of these new systems was established. To confirm their high selectivity and activity, in vitro and in vivo studies were performed to illustrate the abilities of Hex@UPMOF-1 and Hex@UPMOF-2 to combat the known aggressive pathogen Ganoderma boninense that causes basal stem rot disease in oil palm. Accordingly, at an extremely low concentration of 0.05 μg mL-1, both Hex@UPMOF-1 and Hex@UPMOF-2 were demonstrated to completely inhibit (100%) G. boninense growth, and during a 26 week in vivo nursery trial, the progression of basal stem rot infection was completely halted upon treatment with Hex@UPMOF-1 and Hex@UPMOF-2 and seedling growth was accelerated given the additional nutrients supplied via the disassembly of the MOFs. This study represents a significant step forward in the design of adjuvants to support the environmentally responsible use of agrichemical crop protection. | Daniels AS, Gellman AJ, Sykes ECH (2024)
Atomic-scale origin of the enantiospecific decomposition of tartaric acid on chiral copper surfaces.
Chemical communications (Cambridge, England) 60, 8383-8386 [PubMed:38958572]
[show Abstract]
The origin of the enantiospecific decomposition of L- and D-tartaric acid on chiral Cu surfaces is elucidated on a structure-spread domed Cu(110) crystal by spatially resolved XPS and atomic-scale STM imaging. Extensive enantiospecific surface restructuring leads to the formation of surfaces vicinal to Cu(14,17,2) which are responsible for the enantiospecificity. | Liu L, Wang Y, Sun J, Zhang Y, Zhang X, Wu L, Liu Y, Zhang X, Xia Y, Zhang Q, Gao N (2024)
Improved photostability, solubility, hygroscopic stability and antimicrobial activity of fleroxacin by synthesis of fleroxacin-D-tartaric acid pharmaceutical salt.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 203, 114464 [PubMed:39181416]
[show Abstract]
To improve the solubility of the fluoroquinolone drug fleroxacin (FL), based on the previous experience of our research group in synthesizing co-crystals/salts of quinolone drugs to improve the physicochemical properties of drugs, Fleroxacin-D-tartaric acid dihydrate salt (FL-D-TT, C17H19F3N3O3·C4H5O6·2(H2O)), was synthesized for the first time using fleroxacin and D/L-tartaric acid (D/L-TT). Structural characterization of FL-D-TT was carried out using single-crystal X-ray diffraction, infrared spectral analysis (FT-IR) and powder X-ray diffraction (PXRD). Molecular electrostatic potential analysis showed that D-tartaric acid interacted more readily with FL than L-tartaric acid. The solubility of FL-D-TT (9.71 mg/mL, 1.82 mg/mL) was significantly higher compared to FL (0.39 mg/mL, 0.71 mg/mL) in water and buffer solution at pH 7.4. This may be attributed to the formation of charge-assisted hydrogen bonds (CAHBs) between FL and D-TT that facilitates the dissociation of FL cations in the dissolution medium, leading to an increase in FL solubility. This also led to some improvement in the in vitro antimicrobial activity of FL-D-TT against E. coli, S. typhi, and S. aureus. In addition, the hygroscopic stability of FL has been improved. Surprisingly, FL-D-TT had better photostability than FL, which could be attributed to the introduction of D-TT to make the photosensitizing moiety of FL more stable, which led to the improvement of the photostability of FL. | Breunig JL, Lin YC, Pierce JG (2024)
An enantioselective formal synthesis of thienamycin.
Tetrahedron letters 144, 155132 [PubMed:39006392]
[show Abstract]
Thienamycin is a carbapenem antibiotic with potent activity against gram-negative and gram-positive bacteria. Due to its promising activity but lack of chemical stability, thienamycin serves as inspiration for new synthetic antibiotic scaffolds. In this study, we report a nine-step enantioselective formal synthesis of thienamycin. Our route utilizes an asymmetric reduction, enabled by NaBH4 and D-tartaric acid, followed by a series of diastereoselective reactions to access the key azetidinone precursor to thienamycin. This azetidinone precursor could be used as an intermediate to further develop and expand the scope of next-generation beta-lactam antibiotic scaffolds. | Jia X, Liu J, Zhang Y, Jiang X, Zhang J, Wu J (2023)
D-tartaric acid doping improves the performance of whole-cell bacteria imprinted polymer for sensing Vibrio parahaemolyticus.
Analytica chimica acta 1275, 341567 [PubMed:37524461]
[show Abstract]
Whole-cell bacteria imprinted polymer-based sensors still face challenges in the form of the difficulty of removing the template entirely, low affinity, and poor sensitivity. To further improve their performance, it is pivotal to modulate the morphology and chemical properties of imprintied polymer by taking advantage of doping engineering. Here we introduced D-tartaric acid (D-TA) as a dopant and employed pyrrole as a functional monomer to construct D-TA/polypyrrole (PPy)-based bacteria imprinted polymer (DPBIP) sensor for Vibrio parahaemolyticus (VP) detection. It is demonstrated that D-TA doping can synergistically accelerate the removal of template bacteria from imprinted polymers (1.5 h), improve bacteria affinity of imprinted sites (the recognition time of 30 min), and enhance the sensitivity of DPBIP sensor (a detection limit of 19 CFU mL-1). The DPBIP sensor had a linear range of 102∼106 CFU mL-1 and exhibited high selectivity and good repeatability. Moreover, a recovery of 94.8%-105.3% was achieved in drinking water and oyster samples. Therefore, small functional molecules doping opens a new avenue to engineering BIP-based sensors with high performance, holding potential applications in securing food safety. | Zhong Y, Chen Y, Chen L, Hu Y, Xiao X, Xia L, Li G (2023)
Chiral-Controlled Cyclic Chemiluminescence Reactions for the Analysis of Enantiomer Amino Acids.
Analytical chemistry 95, 6971-6979 [PubMed:37068187]
[show Abstract]
The similarity and complexity of chiral amino acids (AAs) in complex samples remain a significant challenge in their analysis. In this work, the chiral metal-organic framework (MOF)-controlled cyclic chemiluminescence (CCL) reaction is developed and utilized in the analysis of enantiomer AAs. The chiral MOF of d-Co0.75Zn0.25-MOF-74 is designed and prepared by modifying the Co0.75Zn0.25-MOF-74 with d-tartaric acid. The developed chiral bimetallic MOF can not only offer the chiral recognize sites but also act as the catalyst in the cyclic luminol-H2O2 reaction. Moreover, a distinguishable CCL signal can be obtained on enantiomer AAs via the luminol-H2O2 reaction with the control of d-Co0.75Zn0.25-MOF-74. The amplified difference of enantiomer AAs can be quantified by the decay coefficient (k-values) which are calculated from the exponential decay fitting of their obtained CCL signals. According to simulation results, the selective recognition of 19 pairs of AAs is controlled by the pore size of the MOF-74 and their hydrogen-bond interaction with d-tartaric acid on the chiral MOF. Furthermore, the k-values can also be used to estimate the change of chiral AAs in complex samples. Consequently, this chiral MOF-controlled CCL reaction is applied to differentiate enantiomer AAs involved in the quality monitoring of dairy products and auxiliary diagnosis, which provides a new approach for chiral studies and their potential applications. | Qin R, Chen H, Wen R, Li G, Meng Z (2023)
Effect of Boric Acid on the Ionization Equilibrium of α-Hydroxy Carboxylic Acids and the Study of Its Applications.
Molecules (Basel, Switzerland) 28, 4723 [PubMed:37375278]
[show Abstract]
To investigate the synergistic catalytic effects of boric acid and α-hydroxycarboxylic acids (HCAs), we analyzed and measured the effects of the complexation reactions between boric acid and HCAs on the ionization equilibrium of the HCAs. Eight HCAs, glycolic acid, D-(-)-lactic acid, (R)-(-)-mandelic acid, D-gluconic acid, L-(-)-malic acid, L-(+)-tartaric acid, D-(-)-tartaric acid, and citric acid, were selected to measure the pH changes in aqueous HCA solutions after adding boric acid. The results showed that the pH values of the aqueous HCA solutions gradually decreased with an increase in the boric acid molar ratio, and the acidity coefficients when boric acid formed double-ligand complexes with HCAs were smaller than those of the single-ligand complexes. The more hydroxyl groups the HCA contained, the more types of complexes could be formed, and the greater the rate of change in the pH. The total rates of change in the pH of the HCA solutions were in the following order: citric acid > L-(-)-tartaric acid = D-(-)-tartaric acid > D-gluconic acid > (R)-(-)-mandelic acid > L-(-)-malic acid > D-(-)-lactic acid > glycolic acid. The composite catalyst of boric acid and tartaric acid had a high catalytic activity-the yield of methyl palmitate was 98%. After the reaction, the catalyst and methanol could be separated by standing stratification. | Yao D, Wang X, Ma L, Wu M, Xu L, Yu Q, Zhang L, Zheng X (2022)
Impact of Weissella cibaria BYL4.2 and its supernatants on Penicillium chrysogenum metabolism.
Frontiers in microbiology 13, 983613 [PubMed:36274712]
[show Abstract]
Lactic acid bacteria (LAB) can produce a vast spectrum of antifungal metabolites to inhibit fungal growth. The purpose of this study was to elucidate the antifungal effect of isolated Weissella cibaria BYL4.2 on Penicillium chrysogenum, the antifungal activity of W. cibaria BYL4.2 against P. chrysogenum was evaluated by the superposition method, results showed that it had obviously antifungal activity against P. chrysogenum. Studying the probiotic properties of BYL4.2 and determining it as beneficial bacteria. Furtherly, different treatments were carried out to characterize the antifungal activity of cell-free supernatant (CFS) produced by W. cibaria BYL4.2, and it was shown that the CFS was pH-dependent, partly heat-sensitive, and was not influenced by proteinaceous treatment. The CFS of W. cibaria BYL4.2 was analyzed by high-performance liquid chromatography (HPLC) and found the highest content of lactic acid. Screening of metabolic markers by a non-targeted metabolomics approach based liquid chromatography-mass spectrometry (LC-MS). The results speculated that organic acid especially detected D-tartaric acid was the main antifungal substance of CFS, which could cause the down-regulation of metabolites in the ABC transporters pathway, thereby inhibiting the growth of P. chrysogenum. Therefore, this study may provide important information for the inhibitory mechanism of W. cibaria BYL4.2 on P. chrysogenum, and provide a basis for further research on the antifungal effect of Weissella. | Badie OH, Basyony AF, Samir R (2022)
Computer-Based Identification of Potential Druggable Targets in Multidrug-Resistant Acinetobacter baumannii: A Combined In Silico, In Vitro and In Vivo Study.
Microorganisms 10, 1973 [PubMed:36296249]
[show Abstract]
The remarkable rise in antimicrobial resistance is alarming for Acinetobacter baumannii, which necessitates effective strategies for the discovery of promising anti-acinetobacter agents. We used a subtractive proteomics approach to identify unique protein drug targets. Shortlisted targets passed through subtractive channels, including essentiality, non-homology to the human proteome, druggability, sub-cellular localization prediction and conservation. Sixty-eight drug targets were shortlisted; among these, glutamine synthetase, dihydrodipicolinate reductase, UDP-N-acetylglucosamine acyltransferase, aspartate 1-decarboxylase and bifunctional UDP-N-acetylglucosamine diphosphorylase/glucosamine-1-phosphate N-acetyltransferase were evaluated in vitro by determining the minimum inhibitory concentration (MIC) of candidate ligands, citric acid, dipicolinic acid, D-tartaric acid, malonic acid and 2-(N-morpholino)ethanesulfonic acid (MES), respectively, which ranged from 325 to 1500 μg/mL except for MES (25 mg/mL). The candidate ligands, citric acid, D-tartaric acid and malonic acid, showed good binding energy scores to their targets upon applying molecular docking, in addition to a significant reduction in A. baumannii microbial load in the wound infection mouse model. These ligands also exhibited good tolerability to human skin fibroblast. The significant increase in the MIC of malonic acid in β-alanine and pantothenate-supplemented media confirmed its selective inhibition to aspartate 1-decarboxylase. In conclusion, three out of sixty-eight potential A. baumannii drug targets were effectively inhibited in vitro and in vivo by promising ligands. | Song G, Kim KM, Lee S, Jeong KS (2021)
Subtle Modification of Imine-linked Helical Receptors to Significantly Alter their Binding Affinities and Selectivities for Chiral Guests.
Chemistry, an Asian journal 16, 2958-2966 [PubMed:34378325]
[show Abstract]
Aromatic helical receptors P-1 and P-2 were slightly modified by aerobic oxidation to afford new receptors P-7 and P-8 with right-handed helical cavities. This subtle modification induced significant changes in the binding properties for chiral guests. Specifically, P-1 was reported to bind d-tartaric acid (Ka =35500 M-1 ), used as a template, much strongly than l-tartaric acid (326 M-1 ). In contrast, its modified receptor P-7 exhibited significantly reduced affinities for d-tartaric acid (3600 M-1 ) and l-tartaric acid (125 M-1 ). More dramatic changes in the affinities and selectivities were observed for P-2 and P-8 upon binding of polyol guests. P-2 was determined to selectively bind d-sorbitol (52000 M-1 ) over analogous guests, but P-8 showed no binding selectivity: d-sorbitol (1890 M-1 ), l-sorbitol (3330 M-1 ), d-arabitol (959 M-1 ), l-arabitol (4970 M-1 ) and xylitol (4960 M-1 ) in 5% (v/v) DMSO/CH2 Cl2 at 25±1 °C. These results clearly demonstrate that even subtle post-modifications of synthetic receptors may significantly alter their binding affinities and selectivities, in particular for guests of long and flexible chains. |
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