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Статті в журналах з теми "Iminosugars, multivalency, organic synthesis"
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Wang, Yali, Jian Xiao, Aiguo Meng, and Chunyan Liu. "Multivalent Pyrrolidine Iminosugars: Synthesis and Biological Relevance." Molecules 27, no. 17 (August 24, 2022): 5420. http://dx.doi.org/10.3390/molecules27175420.
Повний текст джерелаАнотація:
Recently, the strategy of multivalency has been widely employed to design glycosidase inhibitors, as glycomimetic clusters often induce marked enzyme inhibition relative to monovalent analogs. Polyhydroxylated pyrrolidines, one of the most studied classes of iminosugars, are an attractive moiety due to their potent and specific inhibition of glycosidases and glycosyltransferases, which are associated with many crucial biological processes. The development of multivalent pyrrolidine derivatives as glycosidase inhibitors has resulted in several promising compounds that stand out. Herein, we comprehensively summarized the different synthetic approaches to the preparation of multivalent pyrrolidine clusters, from total synthesis of divalent iminosugars to complex architectures bearing twelve pyrrolidine motifs. Enzyme inhibitory properties and multivalent effects of these synthesized iminosugars were further discussed, especially for some less studied therapeutically relevant enzymes. We envision that this comprehensive review will help extend the applications of multivalent pyrrolidine iminosugars in future studies.
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Zelli, Renaud, Pascal Dumy, and Alberto Marra. "Metal-free synthesis of imino-disaccharides and calix-iminosugars by photoinduced radical thiol–ene coupling (TEC)." Organic & Biomolecular Chemistry 18, no. 13 (2020): 2392–97. http://dx.doi.org/10.1039/d0ob00198h.
Повний текст джерелаАнотація:
Deprotected iminosugar alkenes were subjected to thiol–ene coupling with deprotected sugar thiols to afford new imino-disaccharides. Two thiol–ene couplings converted these alkenes into iminosugar thiols and then multivalent iminosugars.
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D'Adamio, G., C. Matassini, C. Parmeggiani, S. Catarzi, A. Morrone, A. Goti, P. Paoli, and F. Cardona. "Evidence for a multivalent effect in inhibition of sulfatases involved in lysosomal storage disorders (LSDs)." RSC Advances 6, no. 69 (2016): 64847–51. http://dx.doi.org/10.1039/c6ra15806d.
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Matassini, Camilla, Stefania Mirabella, Andrea Goti, Inmaculada Robina, Antonio J. Moreno-Vargas, and Francesca Cardona. "Exploring architectures displaying multimeric presentations of a trihydroxypiperidine iminosugar." Beilstein Journal of Organic Chemistry 11 (December 16, 2015): 2631–40. http://dx.doi.org/10.3762/bjoc.11.282.
Повний текст джерелаАнотація:
The synthesis of new multivalent architectures based on a trihydroxypiperidine α-fucosidase inhibitor is reported herein. Tetravalent and nonavalent dendrimers were obtained by means of the click chemistry approach involving the copper azide-alkyne-catalyzed cycloaddition (CuAAC) between suitable scaffolds bearing terminal alkyne moieties and an azido-functionalized piperidine as the bioactive moiety. A preliminary biological investigation is also reported towards commercially available and human glycosidases.
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Lepage, Mathieu L., Alessandra Meli, Anne Bodlenner, Céline Tarnus, Francesco De Riccardis, Irene Izzo, and Philippe Compain. "Synthesis of the first examples of iminosugar clusters based on cyclopeptoid cores." Beilstein Journal of Organic Chemistry 10 (June 23, 2014): 1406–12. http://dx.doi.org/10.3762/bjoc.10.144.
Повний текст джерелаАнотація:
Cyclic N-propargyl α-peptoids of various sizes were prepared by way of macrocyclizations of linear N-substituted oligoglycines. These compounds were used as molecular platforms to synthesize a series of iminosugar clusters with different valency and alkyl spacer lengths by means of Cu(I)-catalysed azide–alkyne cycloadditions. Evaluation of these compounds as α-mannosidase inhibitors led to significant multivalent effects and further demonstrated the decisive influence of scaffold rigidity on binding affinity enhancements.
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McDonnell, Ciaran, Linda Cronin, Julie L. O'Brie, and Paul V. Murphy. "A General Synthesis of Iminosugars." Journal of Organic Chemistry 69, no. 10 (May 2004): 3565–68. http://dx.doi.org/10.1021/jo035763u.
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Sousa, Cristina, Raquel Mendes, Flora Costa, Vera Duarte, António Fortes, and Maria Alves. "Synthesis of Iminosugars from Tetroses." Current Organic Synthesis 11, no. 2 (May 31, 2014): 182–203. http://dx.doi.org/10.2174/15701794113106660074.
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Schneider, Jérémy P., Stefano Tommasone, Paolo Della Sala, Carmine Gaeta, Carmen Talotta, Céline Tarnus, Placido Neri, Anne Bodlenner, and Philippe Compain. "Synthesis and Glycosidase Inhibition Properties of Calix[8]arene-Based Iminosugar Click Clusters." Pharmaceuticals 13, no. 11 (November 5, 2020): 366. http://dx.doi.org/10.3390/ph13110366.
Повний текст джерелаАнотація:
A set of 6- to 24-valent clusters was constructed with terminal deoxynojirimycin (DNJ) inhibitory heads through C6 or C9 linkers by way of Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions between mono- or trivalent azido-armed iminosugars and calix[8]arene scaffolds differing in their valency and their rigidity but not in their size. The power of multivalency to upgrade the inhibition potency of the weak DNJ inhibitor (monovalent DNJ Ki being at 322 and 188 µM for C6 or C9 linkers, respectively) was evaluated on the model glycosidase Jack Bean α-mannosidase (JBα-man). Although for the clusters with the shorter C6 linker the rigidity of the scaffold was essential, these parameters had no influence for clusters with C9 chains: all of them showed rather good relative affinity enhancements per inhibitory epitopes between 70 and 160 highlighting the sound combination of the calix[8]arene core and the long alkyl arms. Preliminary docking studies were performed to get insights into the preferred binding modes.
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Al Bujuq, Nader, and Manuel Angulo. "Synthesis of N-substituted Five and Six-membered Iminocyclitols-bearing Sugar Moiety: Strategy Toward the Synthesis of Pseudodisaccharide." Current Organic Synthesis 15, no. 6 (August 29, 2018): 853–62. http://dx.doi.org/10.2174/1570179415666180601083944.
Повний текст джерелаАнотація:
Aim and Objective: The efficient synthesis of disaccharide containing iminosugar moiety has a considerable interest in the field of glycoscience. In the present work, we describe a novel and applicable method for synthesis of five and six-membered N-substituted iminosugars attached with sugar moiety (pseudodisaccharides). Materials and Methods: The method of the glycosylation was based on the coupling of iminosugar thioglycoside (glycosyl donors) with partially protected sugars (glycosyl acceptors) in the presence of DMTST as a promoter. 2D COSY, HMQC, HMBC experiments were carried out to assist in NMR signal assignments. The pseudoanomeric configuration was established through NOE experiments and molecular modeling calculations. Results: Two classes of pseudodisaccharides were successfully obtained, five and six-membered N-substituted iminosugars glycosides. The six-membered pseudodisaccharides compounds were produced selectively with only β anomer. The corresponding five-membered pseudodisaccharides were achieved with moderate stereoselectivity. The yields obtained were good. These derivatives of iminocyclitols are thought to be precedents to develop various pseudodisaccharides, novel biologically active compounds, and new functional molecules. Conclusion: According to the results, utilizing iminosugar thioglycosides (1 and 2) as a glycosyl donor in glycosylation reactions is an efficient and highly stereoselective method to prepare (five- and six-membered) iminocyclitols (iminosugars) that bear a sugar moiety. The results will add to the synthesis of the iminosugars derivatives and contribute to make our approach among the few methods able to synthesize iminosugar glycosides.
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Esposito, Anna, Daniele D’Alonzo, Maria De Fenza, Eliana De Gregorio, Anna Tamanini, Giuseppe Lippi, Maria Cristina Dechecchi, and Annalisa Guaragna. "Synthesis and Therapeutic Applications of Iminosugars in Cystic Fibrosis." International Journal of Molecular Sciences 21, no. 9 (May 9, 2020): 3353. http://dx.doi.org/10.3390/ijms21093353.
Повний текст джерелаАнотація:
Iminosugars are sugar analogues endowed with a high pharmacological potential. The wide range of biological activities exhibited by these glycomimetics associated with their excellent drug profile make them attractive therapeutic candidates for several medical interventions. The ability of iminosugars to act as inhibitors or enhancers of carbohydrate-processing enzymes suggests their potential use as therapeutics for the treatment of cystic fibrosis (CF). Herein we review the most relevant advances in the field, paying attention to both the chemical synthesis of the iminosugars and their biological evaluations, resulting from in vitro and in vivo assays. Starting from the example of the marketed drug NBDNJ (N-butyl deoxynojirimycin), a variety of iminosugars have exhibited the capacity to rescue the trafficking of F508del-CFTR (deletion of F508 residue in the CF transmembrane conductance regulator), either alone or in combination with other correctors. Interesting results have also been obtained when iminosugars were considered as anti-inflammatory agents in CF lung disease. The data herein reported demonstrate that iminosugars hold considerable potential to be applied for both therapeutic purposes.
Дисертації з теми "Iminosugars, multivalency, organic synthesis"
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Figuccia, Aude L. A. "Total asymmetric syntheses of iminosugars." Thesis, University of Oxford, 2015. http://ora.ox.ac.uk/objects/uuid:7075b45f-e3e1-4ae6-a544-4d6e54d4714e.
Повний текст джерелаАнотація:
This thesis is concerned with the development of ring-closing iodoamination and ringexpansion methodology and its subsequent application to the asymmetric syntheses of pyrrolidine and piperidine iminosugars. Chapter 1 highlights the remarkable biological properties displayed by iminosugars and introduces methods for the formation of the pyrrolidine and piperidine sub-classes. Chapter 2 describes investigations into the ring-closing iodoamination of bishomoallylic amines which occurs with concomitant N-debenzylation to give an iodomethyl pyrrolidine scaffold. Conversion to the corresponding aziridinium species followed by its regioselective intermolecular ring-opening by H2O enabled the synthesis of (+)-2,5-dideoxy-2,5-imino-Dglucitol (DGDP). A protocol for the preparation of its 1-deoxy-1-amino analogue (+)-ADGDP was also developed. Chapter 3 details studies into the ring-expansion of iodomethyl pyrrolidine scaffolds via the trapping of CO2 (from NaHCO3) to produce cyclic carbonates as single diastereoisomers. Subsequent deprotection of these piperidines allowed the syntheses of (−)-1-deoxymannojirimycin (DMJ) and (+)-1-deoxyallonojirimycin (DANJ) to be completed. Chapter 4 delineates investigations into the trapping of alternative “X=C=Y” electrophiles, via the ring-expansion methodology developed in Chapter 3, initially utilising a model system. These studies culminated in the development of the trapping of p-TsNCO and the application of this methodology in the total asymmetric syntheses of (−)-ADMJ and (+)-ADANJ, the 2-deoxy-2-amino analogues of (−)-DMJ and (+)-DANJ, respectively. Chapter 5 contains full experimental procedures and characterisation data for all compounds synthesised in Chapters 2, 3 and 4.
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Parry, Loren L. "The synthesis of branched sugars and iminosugars." Thesis, University of Oxford, 2011. http://ora.ox.ac.uk/objects/uuid:2a511d58-f626-4f7e-aebc-f595b147827a.
Повний текст джерелаАнотація:
Iminosugars, carbohydrate analogues in which nitrogen replaces the endocyclic oxygen, have attracted much interest due to their biological activity. Iminosugars inhibit carbohydrate-processing enzymes, thereby affecting many biological processes. Several iminosugars are licensed drugs, with many more compounds undergoing clinical trials. The main subject of this thesis is the synthesis and evaluation of novel iminosugars, particularly the effects of structural modifications on the biological activity of these compounds. Chapter 1 describes the role of carbohydrate-processing enzymes in the body, and explores the therapeutic applications of iminosugars that arise from their activity against these enzymes. Examples of substituted iminosugars are reviewed, and the effects of substituents on enzyme inhibition are described. Chapter 2 concerns methyl-branched swainsonine derivatives. Swainsonine has shown potential as a cancer treatment through its inhibition of α-mannosidase. The synthesis of (6R)- and (6S)-C-methyl D-swainsonine is described; both compounds were potent and selective α-mannosidase inhibitors (IC50 3.8 μM, 14 μM). Although less active than the parent compound, their selectivity for Golgi mannosidase over lysosomal mannosidase may be more important than the absolute value against the model enzyme. Chapter 3 describes the synthesis of a 2-C-methyl L-fucose derivative. A diastereoselective Kiliani reaction allowed the formation of a single lactone bearing a new quaternary centre. The utility of this intermediate in accessing di-branched iminosugars was explored; however, attempts to introduce nitrogen to the lactone lacked the necessary stereoselectivity. Chapter 4 relates to the synthesis of pyrrolidine iminosugars, specifically methyl amides. Two enantiomeric dihydroxyproline amides were synthesised; the D-proline derivative was a potent β-N-acetylhexosaminidase inhibitor (IC50 values of up to 3.6 μM), but the L-enantiomer was completely inactive. Inhibition of N-acetylhexosaminidases is relevant to the treatment of cancer and lysosomal storage diseases, and this work contributed to a wider project investigating the effects of altered stereochemistry on the biological activity of pyrrolidine amides.
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Ayers, Benjamin James. "The synthesis and biology of iminosugars and their precursors." Thesis, University of Oxford, 2014. http://ora.ox.ac.uk/objects/uuid:2441a224-0e6f-42e9-97d2-63dd3f6c49c3.
Повний текст джерелаАнотація:
Iminosugars are carbohydrate mimics, where the endocyclic ring oxygen has been replaced by nitrogen. This substitution affords these compounds their inhibitory activity towards sugar-processing enzymes (glycosidases) and, as a consequence, their chemotherapeutic potential in the treatment of a broad range of diseases. Several iminosugars are currently in clinical trials or have entered the market as approved drugs. This has consequently led to increasing levels of research into their synthesis and application, both in terms of the development of efficient methodology to access naturally occurring examples, and also to elaborate novel scaffolds. The presence of multiple chiral centres within iminosugars provides a considerable challenge in accessing these targets by asymmetric means, whereas carbohydrates pose a more attractive chiral pool. As such the majority of literature methods have employed this latter method. The focus of the thesis is on the elaboration of robust methodologies to access both naturally occurring and novel iminosugars, and their precursors, from readily available carbohydrate starting materials. Chapter 1 presents an introduction to iminosugars, including an overview of glycosidase inhibition by this class of sugar-mimic, their historical medical usage and the basis for their potential employment in treating diabetes, lysosomal storage disorders (LSDs) and cancer. This chapter also gives a general review of the methods employed in the literature for the assembly of iminosugar scaffolds. Chapter 2 is concerned with the synthesis of iminosugars from the carbohydrate glucuronolactone. This versatile chiron has previously allowed for access to many homochiral targets, and in this thesis is used to access DGJNAc on a gram-scale. This iminosugar has been shown to be a potent α-N-acetylgalactosaminidase inhibitor and is potentially extremely valuable in the treatment of late-stage cancer. Both enantiomers of glucuronolactone are also utilised in the divergent synthesis of every stereoisomer of two classes of five-membered iminosugars; the pyrrolidines (including DMDP), and the proline amides. These compounds demonstrate remarkable biological activity against a panel of glycosidases and hexosaminidases, allowing for the analysis of the structure-activity relationship between these compounds and the target enzymes. Chapter 3 describes the development of a novel, one-pot methodology - a tandem Strecker reaction and iminocyclisation - for the assembly of trihydroxy piperidine α-iminonitriles from a range of unbranched and branched pentose monosaccharides. These piperidine α-iminonitriles are precursors to pipecolic acids which may also be potentially valuable targets in the treatment of cancer.
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Lenagh-Snow, Gabriel Matthew Jack. "The synthesis of azetidine and piperidine iminosugars from monosaccharides." Thesis, University of Oxford, 2012. http://ora.ox.ac.uk/objects/uuid:207235d5-2ea5-4724-92fd-924fa0ccd4ed.
Повний текст джерелаАнотація:
Iminosugars are polyhydroxylated alkaloids, and can be generally defined as sugar mimetics in which the endocyclic oxygen atom has been replaced with a basic nitrogen. A common affect of this atomic substitution is to bestow these compounds with the ability to inhibit various sugarprocessing enzymes; most significantly the glycosidases (glycoside hydrolases) which areintimately involved in a huge array of biological functions. Compounds which inhibit these enzymes concordantly possess much potential as medicinal agents for the treatment of a variety of diseases. Several iminosugars have already achieved market approval as drugs, and many more are promising candidates in the late stages of clinical development. As such there remains considerable interest in this class of compound, both in terms of the exploration of novel iminosugar structures, as well as the continual development of more efficient general methodology for their synthesis. The densely-packed functionality and stereochemical information present in iminosugars makes them challenging targets for asymmetric chemical synthesis, whereas carbohydrates are clearly very attractive as chiral-pool starting materials for this purpose. Indeed, the majority of the most successful syntheses of iminosugars use the latter approach, and such is the focus of this thesis. Chapter 1 presents a relatively brief introduction to iminosugars, including their types of structure, natural occurrence and biological mode of action. The rationale behind their use as therapeutic agents for the treatment of some significant disease targets is also discussed. Chapter 2 is concerned with the preparation of a number of novel polyhydroxylated azetidines, and their evaluation as glycosidase inhibitors. Such compounds represent an almost entirely neglected class of iminosugars within the literature. An overview of natural and synthetic products incorporating an azetidine motif is given, as well as a brief review of preparative methods and known azetidine iminosugars. A highly efficient and flexible method for the key azetidine ring formation is demonstrated by the cyclisations of 3,5-di-O-triflates of pentoses and hexoses, and of a 2,4-di-O-triflate of glucose, with various primary amines. In this manner, many azetidine triols and tetrols were prepared in good yield. Furthermore, this process is readily adaptable to the installation of added functionality to the azetidine scaffold, as demonstrated by the preparation of 1-acetamido analogues. The initial biological screening of these compounds showed a promising array of glycosidase inhibition, including that of selective inhibition of fungal enzymes. Chapter 3 describes a strategy with which to prepare all sixteen stereoisomers of a known piperidine iminosugar, alpha-homonojirimycin (alpha-HNJ), in a highly divergent manner from just four of the possible thirty-two 6-azidoheptitols using traditional chemical synthesis in tandem with biotechnological transformations. One half of the execution of this strategy is described in this thesis. Two 6-azidoheptitols were prepared from D-mannose, thereby providing access to four 6-azidoketoheptoses through a combination of microbial oxidation and enzymatic epimerisation. Catalytic hydrogenation of these 6-azidoketoheptoses furnished four diastereomeric mixtures of 2,6-iminoheptitols, with varying degrees of stereoselectivity. Purification of these mixtures allowed six 2,6-iminoheptitols to be isolated, two of which have never previously been tested for glycosidase inhibition. Significantly, one of them was found to be a potent and highly selectiveinhibitor of alpha-galactosidases, and may therefore be of interest in the treatment of Fabry disease.
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Best, Daniel. "Rare monosaccharides and biologically active iminosugars from carbohydrate chirons." Thesis, University of Oxford, 2011. http://ora.ox.ac.uk/objects/uuid:028392ce-6580-4fb9-bdc3-9be702b951e4.
Повний текст джерелаАнотація:
Iminosugars are polyhydroxylated alkaloids, and can be viewed as sugar analogues in which the endocyclic oxygen atom has been replaced with nitrogen. These compounds are highly medically relevant and their biological activity is largely due to their inhibition of glycosidases. Several examples of the iminosugar class are currently marketed as drugs, and many more are in earlier stages of development for a variety of diseases and disorders. The most fruitful approaches to the chemical synthesis of iminosugars have utilised carbohydrate starting materials as optically pure chiral building blocks, or chirons. Most of the monosaccharides are not readily available, but the relatively few naturally abundant cheap sugars have been exploited as chirons for over a century. The availability of the rare sugars is growing with the development of a new biotechnological approach to their synthesis, known as Izumoring. This thesis is primarily concerned with the chemical synthesis of iminosugars from carbohydrate starting materials. The synthesis of unnaturally functionalised sugar polyols and their suitability as substrates for the Izumoring process is also discussed. Chapter 1 provides a brief general overview of the history, natural occurrence and therapeutic application of iminosugars. General strategies for their synthesis from carbohydrate chirons are discussed. Chapter 2 concerns divergent syntheses of several iminosugar targets from both enantiomers of glucuronolactone and their biological evaluation. A new scaleable synthesis of the natural product 1-deoxynojirimycin is presented that has since been adopted for commercial purposes, as well as an efficient strategy for the synthesis of both enantiomers of 2,5-dideoxy-2,5-imino- mannitol and their novel amino acid analogues. Access to hexosaminidase inhibiting acetamido- substituted piperidines is presented, including 2-acetamido-1,5-imino-1,2,5-trideoxy-D- galactitol, which has been found to be one of the few known potent and specific inhibitors of α- N-acetyl-galactosaminidase. This inhibitory profile may allow the compound’s use for further investigation of a strategy for cancer treatment. Chapter 3 concerns the synthesis of carbon branched pyrrolidines and their biological evaluation. A novel and highly potent α-glycosidase inhibitor has been discovered, synthesised by a strategy that utilises the benzhydryl ether as key protecting group. A mild method for the introduction of this protecting group has been shown to be general to a range of sterically congested and/or acid/base sensitive carbohydrate lactones. Chapter 4 concerns the synthesis of deoxygenated and fluorinated sugar alcohols and their successful biotechnological transformation into ketoses by the Izumoring process. Publications arising from this work are included in the Appendix.
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Shanley, Samantha Jane. "A glycopore for bacterial sensing." Thesis, University of Oxford, 2009. http://ora.ox.ac.uk/objects/uuid:06fe9bce-6bf2-4f61-b4d8-014cb9df3fc0.
Повний текст джерелаАнотація:
Increasing antibiotic resistance has created a need to develop rapid and reliable methods to identify bacteria and provide pertinent information to ensure suitable antibiotics or sugar therapeutics can be chosen for treatment. Carbohydrate structures attached to proteins on host cell surfaces provide a binding point for many pathogens, including bacteria. These structures can be mimicked using single monosaccharides glycosylated to alpha-hemolysin (alpha-HL). Alpha-HL is a beta-barrel pore-forming toxin secreted by Staphylococcus aureus that forms an SDS stable heptamer, which can be expressed by coupled in vitro transcription and translation and purified by polyacrylamide gel electrophoresis. The purified heptamers can be reconstituted into planar lipid bilayers and studied at the single channel level. Through single channel recordings the effects of sugar-linker lengths, different glycans and the interaction between the ‘Glycopore’ and sugar binding molecules can be studied. The glycopore, therefore, acts as a scaffold for analysing protein-sugar interactions. Studies in this thesis have focused on the synthesis of carbohydrates for site-selective protein glycosylation; cloning and in vitro transcription translation of alpha-HL monomers; and glycosylation and oligomerisation of alpha-HL to form glycopores suitable for lectin-binding studies. Lectins DC-SIGN and FimH have been expressed in Escherichia coli and these lectins as well as others have been screened using alpha-HL glycopores. The glycopores have also been investigated with bacteria in serum in a controlled molecule-specific manner using single-channel electrical recording. In this work glycosylated alpha-HL-monomers have been found to form stable heptamers which can be formed by oligomerisation on red blood cell membranes. The purified glycopores were reconstituted into planar lipid bilayers and studied at the single-channel level. Through single-channel recordings an optimised glycopore has been shown to be effective in distinguishing lectins alone and in a mixture and has afforded qualitative and quantitative information about the binding interactions between carbohydrates and sugar binding proteins. Furthermore, the glycopore has been used to sense bacteria which may provide an insight into modes of bacterial infection. In addition, a multivalent glycopore has been formed which has proved preliminary information about the effects of multivalency in lectin binding. The design and synthesis of non-beta-lactam antibiotic candidates and their evaluation has also been carried out.
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Vanni, Costanza. "Studying multivalent iminosugar glycomimtics to target enzymes for healthcare applications." Doctoral thesis, 2020. http://hdl.handle.net/2158/1239110.
Повний текст джерелаАнотація:
The main focus of this PhD thesis is the study of iminosugars as potential glycosidases inhibitors. Two main classes of these carbohydrates mimics have been taken into consideration, namely polyhydroxylated pyrrolidines and piperidines, which were treated from different point of view, in particular in terms of Multivalency, one of the main issues studied in this work. If iminosugars is the pivotal class of molecules under deep examination, different types of glycosidases target have been screened, accordingly to the azasugar nature and to the final application consequently.
Тези доповідей конференцій з теми "Iminosugars, multivalency, organic synthesis"
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Rodriguez-Borges, José, Fabio Rizzo-Aguiar, Cidália Pereira, and Xerardo García-Mera. "Synthesis and Selective Functionalization of Enantiomerically Pure Iminosugars." In The 16th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2012. http://dx.doi.org/10.3390/ecsoc-16-01094.
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Aragão-Leoneti, Valquiria, and Ivone Carvalho. "Simple and efficient synthesis of triazole-based iminosugars with potential anti-glucosidase activity." In 15th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_201382116258.
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Pino-González, M., and Carmen Assiego. "Studies on Inversion of Configuration in the Synthesis of Iminosugars." In The 9th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2005. http://dx.doi.org/10.3390/ecsoc-9-01495.
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