Relevant bibliographies by topics / Glycosidases – Inhibitors – Synthesis

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Academic literature on the topic 'Glycosidases – Inhibitors – Synthesis'

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Published: 4 June 2021
Last updated: 19 February 2022

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Journal articles on the topic "Glycosidases – Inhibitors – Synthesis"

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Le Merrer, Yves, Lydie Poitout, Jean-Claude Depezay, Isabelle Dosbaa, Sabine Geoffroy, and Marie-José Foglietti. "Synthesis of azasugars as potent inhibitors of glycosidases." Bioorganic & Medicinal Chemistry 5, no. 3 (March 1997): 519–33. http://dx.doi.org/10.1016/s0968-0896(96)00266-0.

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Le Merrer, Yves, Myrielle Fuzier, Isabelle Dosbaa, Marie-José Foglietti, and Jean-Claude Depezay. "Synthesis of thiosugars as weak inhibitors of glycosidases." Tetrahedron 53, no. 49 (December 1997): 16731–46. http://dx.doi.org/10.1016/s0040-4020(97)10096-5.

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Andriuzzi, Olivia, Christine Gravier-Pelletier, and Yves Le Merrer. "Synthesis of C8-glycomimetics as potential glycosidases inhibitors." Tetrahedron Letters 45, no. 43 (October 2004): 8043–46. http://dx.doi.org/10.1016/j.tetlet.2004.08.172.

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Puet, Alejandro, Gema Domínguez, Francisco Javier Cañada, and Javier Pérez-Castells. "Synthesis and Evaluation of Novel Iminosugars Prepared from Natural Amino Acids." Molecules 26, no. 2 (January 13, 2021): 394. http://dx.doi.org/10.3390/molecules26020394.

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Cyclopropanated iminosugars have a locked conformation that may enhance the inhibitory activity and selectivity against different glycosidases. We show the synthesis of new cyclopropane-containing piperidines bearing five stereogenic centers from natural amino acids l-serine and l-alanine. Those prepared from the latter amino acid may mimic l-fucose, a natural-occurring monosaccharide involved in many molecular recognition events. Final compounds prepared from l-serine bear S configurations on the C5 position. The synthesis involved a stereoselective cyclopropanation reaction of an α,β-unsaturated piperidone, which was prepared through a ring-closing metathesis. The final compounds were tested as possible inhibitors of different glycosidases. The results, although, in general, with low inhibition activity, showed selectivity, depending on the compound and enzyme, and in some cases, an unexpected activity enhancement was observed.
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Xinhua Qian, Francisco Morís-Varas, and Chi-Huey Wong. "Synthesis of C2-symmetrical polyhydroxyazepanes as inhibitors of glycosidases." Bioorganic & Medicinal Chemistry Letters 6, no. 10 (May 1996): 1117–22. http://dx.doi.org/10.1016/0960-894x(96)00183-7.

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Serbian, Immo, Erik Prell, Claudia Fischer, Hans-Peter Deigner, and René Csuk. "n-Propyl 6-amino-2,6-dideoxy-2,2-difluoro-β-d-glucopyranoside is a good inhibitor for the β-galactosidase from E. coli." Medicinal Chemistry Research 30, no. 5 (March 5, 2021): 1099–107. http://dx.doi.org/10.1007/s00044-021-02715-8.

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AbstractA convenient route has been developed for the synthesis of novel 6-amino-2,2-(or 3,3-difluoro)-2-(or 3),6-dideoxy-hexopyranoses. Biological screening showed these compounds as good inhibitors for several glycosidases. Especially n-propyl 6-amino-2,6-dideoxy-2,2-difluoro-β-d-glucopyranoside (8) was an excellent competitive inhibitor for the β-galactosidase from E. coli holding a Ki of 0.50 μM.
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LE MERRER, Y., M. FUZIER, I. DOSBAA, M. J. FOGLIETTI, and J. C. DEPEZAY. "ChemInform Abstract: Synthesis of Thiosugars as Weak Inhibitors of Glycosidases." ChemInform 29, no. 13 (June 23, 2010): no. http://dx.doi.org/10.1002/chin.199813179.

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Samoshin, Andrey V., Irina A. Dotsenko, Nataliya M. Samoshina, Andreas H. Franz, and Vyacheslav V. Samoshin. "Thio-β-D-glucosides: Synthesis and Evaluation as Glycosidase Inhibitors and Activators." International Journal of Carbohydrate Chemistry 2014 (August 21, 2014): 1–8. http://dx.doi.org/10.1155/2014/941059.

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Structurally simple 1-thio-β-D-glucopyranosides were synthesized and tested as potential inhibitors toward several fungal glycosidases from Aspergillus oryzae and Penicillium canescens. Significant selective inhibition was observed for α- and β-glucosidases, while a weak to moderate activation for α- and β-galactosidases.
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Meloncelli, Peter J., Tracey M. Gloster, Victoria A. Money, Chris A. Tarling, Gideon J. Davies, Stephen G. Withers, and Robert V. Stick. "D-Glucosylated Derivatives of Isofagomine and Noeuromycin and Their Potential as Inhibitors of β-Glycoside Hydrolases." Australian Journal of Chemistry 60, no. 8 (2007): 549. http://dx.doi.org/10.1071/ch07188.

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While isofagomine and noeuromycin have previously been demonstrated to be effective inhibitors of a range of exo-acting glycosidases, they are usually only very weak inhibitors of endo-glycosidases. However, the disaccharide-like 3- and 4-O-β-d-glucopyranosylisofagomines have proven to be strong inhibitors of these endo-acting enzymes that utilize multiple sub-sites. In an attempt to emulate these successes, we have prepared 3- and 4-O-β-d-glucopyranosylnoeuromycin, the former by a selective glycosylation (at O2) of benzyl 4-C-cyano-4-deoxy-α-d-arabinoside (also leading to another synthesis of 3-O-β-d-glucopyranosylisofagomine), the latter by a non-selective glycosylation of benzyl 4-O-allyl-β-l-xyloside with subsequent introduction of the required nitrile group (also leading to another synthesis of 4-O-β-d-glucopyranosylisofagomine). 3-O-β-d-Glucopyranosylnoeuromycin was evaluated as an inhibitor of a family 26 lichenase from Clostridium thermocellum, and 4-O-β-d-glucopyranosylnoeuromycin as an inhibitor of both a family 5 endo-glucanase from Bacillus agaradhaerans and a family 10 endo-xylanase from Cellulomonas fimi. We also report X-ray structural investigations of 3- and 4-O-β-d-glucopyranosylnoeuromycin in complex with the family 26 and family 5 β-glycoside hydrolases, respectively. The two d-glucosylated noeuromycins were indeed able to harness the additional binding energy from the sub-sites of their endo-glycoside hydrolase targets, and were thus excellent inhibitors (in the nanomolar range), binding as expected in the –1 and –2 sub-sites of the enzymes.
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QIAN, X., F. MORIS-VARAS, and C. H. WONG. "ChemInform Abstract: Synthesis of C2-Symmetrical Polyhydroxyazepanes as Inhibitors of Glycosidases." ChemInform 27, no. 37 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199637284.

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Dissertations / Theses on the topic "Glycosidases – Inhibitors – Synthesis"

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Caron, Gaétan. "Synthesis of cyclitol-based glucosidase inhibitors." Thesis, University of British Columbia, 1988. http://hdl.handle.net/2429/27852.

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The first conduritol aziridine (1,2-dideoxy-1,2-epimino-myo-inositol, 1) was synthesized in seven steps from myo-inositol (2) and inhibits pABG5 β-glucosidase and yeast ⍺-glucosidase irreversibly. 1,2-0-Cyclohexylidene-myo-inositol (3) was obtained by reaction of 2 with cyclohexanone. Benzylation of 3 followed by hydrolysis of the ketal gave l,4,5,6-tetra-0-benzyl-myo-inositol (5). The two free hydroxyl groups in 5 were methanesulfonylated and the axial mesyl group in l,4,5,6-tetra-0-benzyl-2,3-di-0-methanesulfonyl-myo-inositol (12) was selectively displaced by an azido group. The resulting 1-azido-2,3,4,5-tetxa-0-benzyl-1-deoxy-6-0-methanesulfonyl-scyllo-inositol (13) was hydrogenated in the presence of HC1 to give 1-amino-1-deoxy-2-0-methanesulfonyl-scyllo-inositol (24) hydrochloride. Cyclisation of 24 under basic aqueous conditions yielded DL-1. [Formula Omitted] The dissociation constant Ki and the inactivation rate constant ki for inactivation of pABG5 β-glucosidase by 1 were calculated to be 3.0 mM and 0.077 min⁻¹ respectively. For yeast ⍺-glucosidase inactivation, values of Ki, and ki were found to be 9.5 mM and 0.39 min-1 respectively. Finally, 24 and 31 were tested as reversible (non-covalent) inhibitors of both the glucosidases and the respective inhibition constants (Ki) determined.
Science, Faculty of
Chemistry, Department of
Graduate
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Meloncelli, Peter J. "The synthesis of several azasugars, glycosylated azasugars and disaccharides of biological interest." University of Western Australia. School of Biomedical, Biomolecular and Chemical Sciences, 2007. http://theses.library.uwa.edu.au/adt-WU2007.0052.

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[Truncated abstract] The development of several carbohydrate-based pharmaceuticals has stimulated an increased interest in the field of carbohydrate chemistry. The discovery of Acarbose and invention of Miglitol, treatments for type II diabetes, as well as the influenza treatments, Relenza and Tamiflu, have been largely responsible for this increased interest. These treatments operate by the inhibition of glycoside hydrolases, a group of enzymes important in a variety of biological processes. This thesis involves the study of a group of glycoside hydrolase inhibitors known as azasugars, which are nitrogen-containing sugar mimics . . . The final chapter, Chapter 4, focuses on the testing of these disaccharides as a possible alternative carbohydrate source for pre-term infants. Initially, commercially available glycoside hydrolases were used to detect any hydrolysis of the four disaccharides, with (206) exhibiting the most promising results (to provide D-glucose and D-galactose). Detailed kinetic studies were then conducted using homogenates obtained from pig intestinal mucosa. Unfortunately, the results indicated that (206) was unsuitable as an alternative carbohydrate source for pre-term infants.
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Miglioli, Francesca. "Synthesis and biological evaluation of bicyclic iminosugar derivatives as inhibitors of glycosidases." Master's thesis, Alma Mater Studiorum - Università di Bologna, 2018. http://amslaurea.unibo.it/16676/.

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During this work, five pyrrolizidine derivatives and one isoxazolidine derivative have been synthetized in order to evaluate their biological activities towards glycosidases, related to their configurations and type of bridge functionalities between the bicyclic iminosugar moiety and the aromatic part of the molecules. The final pyrrolizidine derivatives have been synthetized through click reactions (urea forming reaction, thiourea forming reaction and CuAAC reaction) performed on a common amino-pyrrolizidine precursor. The final isoxazolidine derivative has been synthetized through a CuAAC reaction. In addition, an indolizidine scaffold was obtained through a ring-closing metathesis on a dialkenyl pyrrolidine. This bicyclic compound could be of interest as intermediate for the synthesis of indolizidine derivatives with potential as glycosidase inhibitors. Biological evaluation towards glycosidases of the final six compounds synthetized in this work revealed that all of these compounds show inhibition towards almonds’ β-glucosidase and/or jack beans’ α-mannosidase.
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Scaffidi, Adrian. "Synthetic endeavours in carbohydrates." University of Western Australia. School of Biomedical, Biomolecular and Chemical Sciences, 2007. http://theses.library.uwa.edu.au/adt-WU2007.0114.

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The overwhelming occurrence and structural diversity of carbohydrates in Nature indicate their importance in a range of fundamental life processes. Indeed, it is this diversity that has lead to the two equally diverse groups of carbohydrate-processing enzymes, namely the glycoside hydrolases and glycosyl transferases. Thus, understanding the role of both carbohydrates and their processing enzymes in biological systems has attracted significant attention. This thesis, firstly, describes endeavours towards the synthesis of an inositol ?- amino acid, along with a series of sugar α-substituted carboxylic acid esters, utilising an extension of the modified Corey-Link reaction. The emphasis of the thesis is then shifted towards the synthesis of a putative inhibitor of a family GH26 lichenase from Clostridium thermocellum (CtLic26A). The preparation of 2-deoxy-2-fluoro-β-laminarbiosyl fluoride 1 is described, along with elaboration into oligosaccharides utilising AbgE358G glycosynthase technology. Crystallographic investigations indicated that the transition state adopted by CtLic26A is in stark contrast to that utilised by the related family GH26 mannanase from Pseudomonas cellulose (Man26A). ... Following on from this work, expanding the role of the AbgE358G glycosynthase acceptor repertoire to accommodate inositol substrates was explored, furthering the synthetic utility of this enzyme. Thus, a number of inositol acceptors bearing an aryl anchor, for example 2, were prepared and shown to be surrogates for carbohydrate acceptors. ... The thesis then describes the synthesis of an acetamide derivative of 1-epivalienamine, namely 3, a putative inhibitor of β-N-acetylglucosaminidases. Both the synthesis of 3, along with kinetic data for four β-N-acetylglucosaminidases, is reported; as well, Western blot analysis indicated no inhibition of a recombinant OGTase. ... Related to the preparation of a putative inhibitor of β-N-acetylglucosaminidases was the synthesis of a conformationally rigid carbocycle derivative of PUGNAc 4, along with two other derivatives 5 and 6. These compounds were also tested against four β-N-acetylglucosaminidases and a recombinant OGTase. ... Finally, the synthesis of a mechanism-based inhibitor of family GH3 β-Nacetylglucosaminidases, namely 2-acetamido-2-deoxy-5-fluoro-β-D-glucopyranosyl fluoride 7, is described. The incorporation of an azido moiety allows for the utilisation of 8 as an effective probe of β-N-acetylglucosaminidases. ...
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Heightman, Tom Daniel. "O-glycosidases under scrutiny: synthesis of inhibitors and structural probes : and Synthesis of a potential DNA-binding pseudotetrasaccharide /." Zürich, 1998. http://e-collection.ethbib.ethz.ch/show?type=diss&nr=12696.

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Carpenter, Neil M. "Studies on glycosidase inhibitors." Thesis, University of Oxford, 1989. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.236101.

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Namgoong, Sung Keon. "The synthesis of glycosidase inhibitors." Thesis, University of Oxford, 1989. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.236199.

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Ong, Quyen Binh. "An enantioselective synthesis of glycosidase inhibitors." Thesis, King's College London (University of London), 1999. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.314209.

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Dedola, Simone. "'Click chemistry' to synthesise potential glycosidase inhibitors." Thesis, University of East Anglia, 2009. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.502211.

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In this study, "click chemistry" was used to assemble a collection of potential glycosidase inhibitors. Using different "click chemistry" conditions, 21 α-D- and β-D glucopyranosyl triazoles were synthesised and assayed as inhibitors of sweet almond β-glucosidase and yeast α-glucosidase. A set of moderately effective glycosidase inhibitors was identified. In the course of this work significant differences in the reactivity of the α- and β-glucopyranosyl azides under CuAAC conditions was noted. This matter was investigated by X-ray crystallography and, in keeping with the anomeric effect, pointed to a difference in partial charge distribution in the azide and sugar moieties. Starting from maltosyl and maltotriosyl azides another collection of 12 triazoles was synthesised and all of the libraries were assayed against starch degrading enzymes from barley. A moderate inhibitor of α-glucosidase was identified, as were several weak inhibitors of β-amylase.
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Nkansah, Peter Appah. "Syntheses of pyridylglucoconjugates as potential glycosidase inhibitors." Thesis, University of East Anglia, 2001. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.368182.

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Book chapters on the topic "Glycosidases – Inhibitors – Synthesis"

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de Raadt, Anna, Christian W. Ekhart, Michael Ebner, and Arnold E. Stütz. "Chemical and chemo-enzymatic approaches to glycosidase inhibitors with basic nitrogen in the sugar ring." In Glycoscience Synthesis of Substrate Analogs and Mimetics, 157–86. Berlin, Heidelberg: Springer Berlin Heidelberg, 1997. http://dx.doi.org/10.1007/bfb0119256.

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Nishimura, Yoshio. "Glycosidase and Glycosyltransferase Inhibitors." In Stereoselective Synthesis, 495–583. Elsevier, 1992. http://dx.doi.org/10.1016/b978-0-444-89558-5.50038-9.

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Bols, M., Ó. López, and F. Ortega-Caballero. "Glycosidase Inhibitors: Structure, Activity, Synthesis, and Medical Relevance." In Comprehensive Glycoscience, 815–84. Elsevier, 2007. http://dx.doi.org/10.1016/b978-044451967-2/00100-8.

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Nishimura, Yoshio. "Stereoselective synthesis and transformation of siastatin B, A novel glycosidase inhibitor, directed toward new drugs for viral infection and tumor metastasis." In Stereoselective Synthesis (Part J), 75–121. Elsevier, 1995. http://dx.doi.org/10.1016/s1572-5995(06)80053-0.

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Conference papers on the topic "Glycosidases – Inhibitors – Synthesis"

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Malle, Birgitte M., Morten B. Norgaard, and Inge Lundt. "SYNTHESIS OF DEOXYIMINOURONIC ACIDS - EASY ACCESS TO GLYCURONIDASE AND GLYCOSIDASE INHIBITORS." In XXIst International Carbohydrate Symposium 2002. TheScientificWorld Ltd, 2002. http://dx.doi.org/10.1100/tsw.2002.449.

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Ghavami, Ahmad, Blair D. Johnston, Morten T. Jensen, Birte Svenson, and Morten B. Mario Pinto. "SYNTHESIS OF A NEW CLASS OF GLYCOSIDASE INHIBITORS: SALACINOL, ITS STEREOISOMERS, AND NITROGEN AND SELENIUM ANALOGUES, AND THEIR EVALUATION AS GLYCOSIDASE INHIBITORS." In XXIst International Carbohydrate Symposium 2002. TheScientificWorld Ltd, 2002. http://dx.doi.org/10.1100/tsw.2002.510.

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Sakaba, Ai, Katsuhiko Suzuki, and Masanori Yamaura. "REACTIONS OF CYCLIC NITRONES AND NUCLEOPHILES: A STRATEGY FOR THE SYNTHESIS OF PYRROLIDINES GLYCOSIDASE INHIBITORS." In XXIst International Carbohydrate Symposium 2002. TheScientificWorld Ltd, 2002. http://dx.doi.org/10.1100/tsw.2002.633.

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Aghajari, Nushin, Michel Roth, and Richard Haser. "EVIDENCE OF OLIGOSACCHARIDE SYNTHESIS BY CRYSTALS OF A COLD-ACTIVE ALPHA-AMYLASE: CHARACTERIZATION OF A NEW ALPHA-GLYCOSIDASE INHIBITOR." In XXIst International Carbohydrate Symposium 2002. TheScientificWorld Ltd, 2002. http://dx.doi.org/10.1100/tsw.2002.588.

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