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

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Published: 4 June 2021

Last updated: 19 February 2022

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1

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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2

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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3

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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4

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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5

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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6

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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7

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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8

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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9

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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10

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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11

Gauzy, Laurence, Yves Le Merrer, Jean-Claude Depezay, Dominique Damour-Barbalat, and Serge Mignani. "Synthesis of C2-symmetric bis(cyclic isothioureas) as potent inhibitors of glycosidases." Tetrahedron Letters 40, no. 19 (May 1999): 3705–8. http://dx.doi.org/10.1016/s0040-4039(99)00593-6.

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12

Le Merrer, Yves, Laurence Gauzy, Christine Gravier-Pelletier, and Jean-Claude Depezay. "Synthesis of C 2 -symmetric guanidino-sugars as potent inhibitors of glycosidases." Bioorganic & Medicinal Chemistry 8, no. 2 (February 2000): 307–20. http://dx.doi.org/10.1016/s0968-0896(99)00294-1.

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13

McCarter, J. D., M. J. Adam, N. G. Hartman, and S. G. Withers. "In vivo inhibition of β-glucosidase and β-mannosidase activity in rats by 2-deoxy-2-fluoro-β-glycosyl fluorides and recovery of activity in vivo and in vitro." Biochemical Journal 301, no. 2 (July 15, 1994): 343–48. http://dx.doi.org/10.1042/bj3010343.

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2-Deoxy-2-fluoro-beta-glucosyl and -beta-mannosyl fluorides administered to rats in a single dose (10 mg/kg) inhibited beta-glucosidase and beta-mannosidase activity respectively after 1 h in brain, spleen, liver and kidney tissues. This inhibition, presumably caused by accumulation of 2-deoxy-2-fluoroglycosyl-enzyme intermediates, indicates that intact 2-deoxy-2-fluoroglycosyl fluorides are distributed to these organs and, in the case of brain, that they cross the blood/brain barrier. beta-Glucosidase activity recovered completely or partially in brain, spleen, liver and kidney by 20-48 h. beta-Mannosidase activity partially recovered in all tissues by 48 h. beta-Galactosidase activity in brain and kidney was not significantly affected by administration of either the gluco or manno compounds at this dosage, indicating that these inhibitors are directed towards specific glycosidases. Observation of similar relatively rapid rates of beta-glycosidase re-activation in vivo and in tissue homogenates in vitro at 37 degrees C suggests that hydrolysis or transglycosylation of 2-deoxy-2-fluoroglycosyl-enzymes, not protein synthesis, are the primary mechanisms involved in the recovery of glycosidase activity inhibited by this class of compounds in vivo.

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14

Mohal, Narinder, and Andrea Vasella. "Synthesis of Fusion-Isomeric Imidazopyridines and Their Evaluation as Inhibitors ofsyn- andanti-Protonating Glycosidases." Helvetica Chimica Acta 88, no. 1 (January 2005): 100–119. http://dx.doi.org/10.1002/hlca.200490287.

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15

Zhang, Ran, John D. McCarter, Curtis Braun, Wai Yeung, Gary D. Brayer, and Stephen G. Withers. "Synthesis and Testing of 2-Deoxy-2,2-Dihaloglycosides as Mechanism-Based Inhibitors of α-Glycosidases." Journal of Organic Chemistry 73, no. 8 (April 2008): 3070–77. http://dx.doi.org/10.1021/jo702565q.

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16

Panday, Narendra. "Synthesis of Glucose- and Mannose-Derived N-Acetylamino Imidazopyridines and their Evaluation as Inhibitors of Glycosidases." Synthesis 1999, S1 (August 1999): 1459–68. http://dx.doi.org/10.1055/s-1999-3654.

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17

WILLIAMS, J. M. "ChemInform Abstract: Synthesis of Inhibitors of the Glycosidases and Glycosyltransferases Involved in the Biosynthesis and Degradation of Glycoproteins." ChemInform 28, no. 50 (August 2, 2010): no. http://dx.doi.org/10.1002/chin.199750327.

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18

Skelton, Timothy P., Chunxun Zeng, Aaron Nocks, and Ivan Stamenkovic. "Glycosylation Provides Both Stimulatory and Inhibitory Effects on Cell Surface and Soluble CD44 Binding to Hyaluronan." Journal of Cell Biology 140, no. 2 (January 26, 1998): 431–46. http://dx.doi.org/10.1083/jcb.140.2.431.

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Glycosylation has been implicated in the regulation of CD44-mediated cell binding of hyaluronan (HA). However, neither the relative contribution of N- and O-linked glycans nor the oligosaccharide structures that alter CD44 affinity for HA have been elucidated. To determine the effect of selective alteration of CD44 oligosaccharide composition on the affinity of CD44 for HA, we developed a novel strategy based on the use of affinity capillary electrophoresis (ACE). Soluble recombinant CD44–immunoglobulin fusion proteins were overproduced in the mutant CHO cell line ldl-D, which has reversible defects in both N- and O-linked oligosaccharide synthesis. Using this cell line, a panel of recombinant glycosidases, and metabolic glycosidase inhibitors, CD44 glycoforms with defined oligosaccharide structures were generated and tested for HA affinity by ACE. Because ldl-D cells express endogenous cell surface CD44, the effect of any given glycosylation change on the ability of cell surface and soluble CD44 to bind HA could be compared. Four distinct oligosaccharide structures were found to effect CD44-mediated HA binding: (a) the terminal α2,3-linked sialic acid on N-linked oligosaccharides inhibited binding; (b) the first N-linked N-acetylglucosamine residue enhanced binding; (c) O-linked glycans on N-deglycosylated CD44 enhanced binding; and (d) N-acetylgalactosamine incorporation into non–N-linked glycans augmented HA binding by cell surface CD44. The first three structures induced up to a 30-fold alteration in the intrinsic CD44 affinity for HA (Kd = 5 to >150 μM). The fourth augmented CD44-mediated cellular HA avidity without changing the intrinsic HA affinity of soluble CD44.

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19

Withers, Stephen G. "1998 Hoffmann La Roche Award Lecture Understanding and exploiting glycosidases." Canadian Journal of Chemistry 77, no. 1 (January 1, 1999): 1–11. http://dx.doi.org/10.1139/v98-235.

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Glycosidases fall into two major mechanistic classes; those that hydrolyse the glycosidic bond with retention of anomeric configuration and those that do so with inversion. Retaining glycosidases employ a mechanism involving a covalent glycosyl-enzyme intermediate formed and hydrolysed with acid-base catalytic assistance via oxocarbenium ion-like transition states. This intermediate has been trapped in two distinct ways, either by modification of the substrate through fluorination, or of the enzyme through mutation of key residues. This allows the amino acid residue to which this sugar is attached to be identified through LC/MS-MS analysis of peptic digests. Three-dimensional structures of several of these glycosyl-enzyme complexes, along with those of Michaelis complexes, have been determined through X-ray crystallographic analysis, revealing the identities of important amino acid residues involved in catalysis, particularly the involvement of the catalytic nucleophile in strong hydrogen bonding to the sugar 2-hydroxyl. They have also revealed evidence of substantial substrate distortion upon binding. Insight into the function of the acid-base catalyst Glu172 in Bacillus circulans xylanase has been obtained through NMR titration of side chain 13C-labelled glutamic acid enzyme both free and in the 2-fluoroxylobiosyl-enzyme complex. The pKa of Glu172 is relatively high in the free enzyme, consistent with its role as an acid catalyst, but drops 2.5 units upon formation of the intermediate, consistent with its new role as a base catalyst. This "cycling" of the pKa is shown to be a direct consequence of the change in charge of the nucleophile, Glu78. Finally, an efficient catalyst for synthesis, but not hydrolysis, of glycosidic bonds has been generated by mutation of the glutamic acid catalytic nucleophile of a β-glucosidase to an alanine. When used with alpha-glucosyl fluoride as a glycosyl donor, along with a suitable acceptor, oligosaccharides up to five sugars in length have been made with yields of up to 90% on individual steps. These new enzymes have been named glycosynthases.Key words: enzymatic mechanism, glycoside hydrolysis, inhibitors

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20

Carroll, Anthony W., and Stephen G. Pyne. "The History of the Glycosidase Inhibiting Hyacinthacine C-type Alkaloids: From Discovery to Synthesis." Current Organic Synthesis 16, no. 4 (July 4, 2019): 498–522. http://dx.doi.org/10.2174/1570179416666190126100312.

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Background: The inherent glycosidase inhibitory activity and potentially therapeutic value of the polyhydroxylated pyrrolizidine alkaloids containing a hydroxymethyl substituent at the C-3 position have been well documented. Belonging to this class, the naturally occurring hyacinthacine C-type alkaloids are of general interest among iminosugar researchers. Their selective micromolar α -glycosidase inhibitory ranges (10 – 100 μM) suggest that these azasugars are potential leads for treating type II diabetes. However, the structures of hyacinthacine C1, C3 and C4 are insecure with hyacinthacine C5 being recently corrected. Objective: This review presents the hyacinthacine C-type alkaloids: their first discovery to the most recent advancements on the structures, biological activities and total synthesis. Conclusion: The hyacinthacine C-type alkaloids are of exponentially increasing interest and will undoubtedly continue to be reported as synthetic targets. They represent a challenging but rewarding synthetic feat for the community of those interested in accessing biologically active iminosugars. Since 2009, ten total syntheses have been employed towards accessing similarly related products but only three have assessed the glycosidase inhibitory activity of the final products. This suggests the need for an accessible and universal glycosidase inhibitory assay so to accurately determine the structure-activity relationship of how the hyacinthacine C-type alkaloids inhibit specific glycosidases. Confirming the correct structures of the hyacinthacine C-type alkaloids as well as accessing various analogues continues to strengthen the foundation towards a marketable treatment for type II diabetes and other glycosidase related illnesses.

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21

Bird, P., D. H. Dolphin, and S. G. Withers. "The synthesis of protected 5-azido-5-deoxy-D-glucononitriles as precursors of glycosidase inhibitors." Canadian Journal of Chemistry 68, no. 2 (February 1, 1990): 317–22. http://dx.doi.org/10.1139/v90-045.

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The successful syntheses of 5-azido-2,3,4,6-tetra-O-benzyl-5-deoxy-D-glucononitrile and 2,3,4,6-tetra-O-benzyl-5-deoxy-5-trifluoroacetamido-D-glucononitrile starting from D-glucose are described. Unsuccessful attempts were made to convert these two compounds into a protected 5-amino-5-deoxy-D-glucononitrile and to subsequently cyclize them to an amidine analogue of glucose as a possible glycosidase inhibitor. Keywords: synthesis, amino-sugars, glycosidase inhibitors.

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22

Csuk, René, Stefan Reißmann, Ralph Kluge, Dieter Ströhl, and Claudia Korb. "First Total Synthesis of 3-Epi-calystegin B2." Zeitschrift für Naturforschung B 66, no. 3 (March 1, 2011): 317–23. http://dx.doi.org/10.1515/znb-2011-0315.

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A straightforward chiral pool synthesis for a non-natural calystegin, 3-epi-B2, is described. Key steps of this synthesis include an ultrasound-assisted Zn-mediated tandem ring opening reaction followed by a Grubbs’ catalyst-mediated ring closure metathesis reaction. Compared to calystegin B2, the target compound is no longer an inhibitor for a β -glycosidase hence proving that an equatorial hydroxyl group at position C-3 is necessary for a tight binding of calystegins into the active site of β -glycosidases.

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23

Lee, Jae Chul, Subhashree Francis, Dinah Dutta, Vijayalaxmi Gupta, Yan Yang, Jin-Yi Zhu, Joseph S. Tash, Ernst Schönbrunn, and Gunda I. Georg. "Synthesis and Evaluation of Eight- and Four-Membered Iminosugar Analogues as Inhibitors of Testicular Ceramide-Specific Glucosyltransferase, Testicular β-Glucosidase 2, and Other Glycosidases." Journal of Organic Chemistry 77, no. 7 (March 20, 2012): 3082–98. http://dx.doi.org/10.1021/jo202054g.

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24

Mohan, Sankar, and B. Mario Pinto. "Sulfonium-ion glycosidase inhibitors isolated from Salacia species used in traditional medicine, and related compounds." Collection of Czechoslovak Chemical Communications 74, no. 7-8 (2009): 1117–36. http://dx.doi.org/10.1135/cccc2009024.

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A novel class of naturally-occurring glycosidase inhibitors, having sulfonium sulfate structures, has been isolated as bioactive components from Indian plants, belonging to the Salacia genus in the family Celastraceae, and used in Ayurvedic medicine for the treatment of type-2 diabetes. Thus far, five such sulfonium salts, namely, salacinol, kotalanol, salaprinol, ponkoranol and de-O-sulfonated kotalanol, have been isolated from this plant species. These structurally unique zwitterionic glycosidase inhibitors have received much attention due to their therapeutic potential in the treatment of type-2 diabetes. We recently reported a review article which focused mainly on salacinol and related analogues. The present review presents an update on the remaining four compounds from this class of glycosidase inhibitors, with respect to their isolation, glucosidase inhibitory activities, and synthesis. In addition, progress towards the stereochemical structure elucidation of kotalanol, through synthesis of analogues, is described. Review with 42 references.

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25

Uchida, Chikara, and Seiichiro Ogawa. "Synthesis and inhibitory activity of glycosidase inhibitors, glycosylamino-oxazolines." Bioorganic & Medicinal Chemistry 4, no. 2 (February 1996): 275–81. http://dx.doi.org/10.1016/0968-0896(95)00181-6.

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26

Hines, Jennifer V., Heesun Chang, Melinda S. Gerdeman, and Dana E. Warn. "Isotope edited NMR studies of glycosidases: design and synthesis of a novel glycosidase inhibitor." Bioorganic & Medicinal Chemistry Letters 9, no. 9 (May 1999): 1255–60. http://dx.doi.org/10.1016/s0960-894x(99)00175-4.

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27

Viuff, Agnete H., and Henrik H. Jensen. "Synthesis and evaluation of N-alkylated analogues of aza-galacto-fagomine – potential pharmacological chaperones for Krabbe disease." Organic & Biomolecular Chemistry 14, no. 36 (2016): 8545–56. http://dx.doi.org/10.1039/c6ob01309k.

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Seven novel alkylated or acylated analogues of hexahydropyridazine aza-galacto-fagomine (AGF) was prepared and studied as glycosidase inhibitors with the aim of increasing inhibitory potency and selectivity.

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28

Liu, Hui, and B. Mario Pinto. "Synthesis of zwitterionic selenonium and sulfonium sulfates from D-mannose as potential glycosidase inhibitors." Canadian Journal of Chemistry 84, no. 4 (April 1, 2006): 497–505. http://dx.doi.org/10.1139/v06-027.

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Four chain-extended analogues of the naturally occurring glycosidase inhibitor salacinol were synthesized for structureactivity studies with different glycosidase enzymes. The syntheses involved the reaction of isopropylidene-protected 1,4-thio- and 1,4-seleno-D-talitols and 1,5-thio- and 1,5-seleno-L-gulitols, derived from D-mannose, with a benzylidene- and isopropylidene-protected 1,3-cyclic sulfate, also derived from D-mannose. Deprotection of the products afforded the novel selenonium and sulfonium sulfates composed of heterocyclic five- and six-membered ring core structures with pendant polyhydroxylated, acyclic chains of six carbon atoms.Key words: glycosidase inhibitors, zwitterionic selenonium and sulfonium sulfates, cyclic sulfate

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29

Hines, Jennifer V., Heesun Chang, Melinda S. Gerdeman, and Dana E. Warn. "ChemInform Abstract: Isotope Edited NMR Studies of Glycosidases: Design and Synthesis of a Novel Glycosidase Inhibitor." ChemInform 30, no. 36 (June 13, 2010): no. http://dx.doi.org/10.1002/chin.199936229.

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30

Nasi, Ravindranath, Lyann Sim, David R. Rose, and B. Mario Pinto. "Synthesis and glycosidase inhibitory activities of chain-modified analogues of the glycosidase inhibitors salacinol and blintol." Carbohydrate Research 342, no. 12-13 (September 2007): 1888–94. http://dx.doi.org/10.1016/j.carres.2007.02.020.

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31

Sánchez-Fernández, Elena M., M. Isabel García-Moreno, Raquel García-Hernández, José M. Padrón, José M. García Fernández, Francisco Gamarro, and Carmen Ortiz Mellet. "Thiol-ene "Click" Synthesis and Pharmacological Evaluation of C-Glycoside sp2-Iminosugar Glycolipids." Molecules 24, no. 16 (August 8, 2019): 2882. http://dx.doi.org/10.3390/molecules24162882.

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The unique stereoelectronic properties of sp2-iminosugars enable their participation in glycosylation reactions, thereby behaving as true carbohydrate chemical mimics. Among sp2-iminosugar conjugates, the sp2-iminosugar glycolipids (sp2-IGLs) have shown a variety of interesting pharmacological properties ranging from glycosidase inhibition to antiproliferative, antiparasitic, and anti-inflammatory activities. Developing strategies compatible with molecular diversity-oriented strategies for structure–activity relationship studies was therefore highly wanted. Here we show that a reaction sequence consisting in stereoselective C-allylation followed by thiol-ene “click” coupling provides a very convenient access to α-C-glycoside sp2-IGLs. Both the glycone moiety and the aglycone tail can be modified by using sp2-iminosugar precursors with different configurational profiles (d-gluco or d-galacto in this work) and varied thiols, as well as by oxidation of the sulfide adducts (to the corresponding sulfones in this work). A series of derivatives was prepared in this manner and their glycosidase inhibitory, antiproliferative and antileishmanial activities were evaluated in different settings. The results confirm that the inhibition of glycosidases, particularly α-glucosidase, and the antitumor/leishmanicidal activities are unrelated. The data are also consistent with the two later activities arising from the ability of the sp2-IGLs to interfere in the immune system response in a cell line and cell context dependent manner.

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32

Johnston, Blair D., Ahmad Ghavami, Morten T. Jensen, Birte Svensson, and B. Mario Pinto. "Synthesis of Selenium Analogues of the Naturally Occurring Glycosidase Inhibitor Salacinol and Their Evaluation as Glycosidase Inhibitors†." Journal of the American Chemical Society 124, no. 28 (July 2002): 8245–50. http://dx.doi.org/10.1021/ja020299g.

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33

Mehta, Goverdhan, and Senaiar S. Ramesh. "Polycyclitols Novel conduritol and carbasugar hybrids as new glycosidase inhibitors." Canadian Journal of Chemistry 83, no. 6-7 (June 1, 2005): 581–94. http://dx.doi.org/10.1139/v05-032.

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A family of novel carbasugar analogues (bicyclitols) based on cis-hydrindane and cis-decalin frameworks has been conceptualized. These novel entities can be regarded as conduritol and carbasugar hybrids. Syntheses of these polyhydroxylated entities have been achieved in stereo- and regioselective manners, starting from the readily available DielsAlder adducts of 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene and appropriate dienophiles like cyclopentadiene or p-benzoquinone, that embody a masked 7-ketonorbornenone moiety. Thermally induced chelotropic elimination of CO from the appropriately functionalized 7-ketonorbornenone derivatives to deliver annulated bicyclic 1,3-cyclohexadiene derivatives was the key step in this synthetic endeavor. Further oxy-functionalization of the 1,3-cyclohexadiene moiety delivered the targeted polycyclitols. A preliminary investigation of the glycosidase inhibitory potency of these bicyclitols, identified compounds 18 and 54 as potent and selective inhibitors of α-glucosidase (yeast).Key words: carbasugar, conduritol, glycomimics, glycosidase inhibitors.

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34

UCHIDA, Chikara, and Seiichiro OGAWA. "Design and Synthesis of Glycosidase Inhibitors." Kagaku To Seibutsu 34, no. 3 (1996): 161–71. http://dx.doi.org/10.1271/kagakutoseibutsu1962.34.161.

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35

Qian, Kang, Han Wang, Jieming Liu, Shuting Gao, Weiting Liu, Xi Wan, Yuanyuan Zhang, Qing-Shan Liu, and Xiao-Ying Yin. "Synthesis of α-glycosidase hybrid nano-flowers and their application for enriching and screening α-glycosidase inhibitors." New Journal of Chemistry 42, no. 1 (2018): 429–36. http://dx.doi.org/10.1039/c7nj03545d.

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To rapidly and accurately screen compounds present in traditional Chinese herbal medicines for α-glycosidase inhibitors, we synthesized a novel nano-affinity material to enable the targeted screening of α-glycosidase inhibitors.

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36

Gandy, Michael N., Matthew J. Piggott, and Keith A. Stubbs. "An Expeditious Synthesis of Iminosugars." Australian Journal of Chemistry 63, no. 10 (2010): 1409. http://dx.doi.org/10.1071/ch10211.

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37

Zelli, Renaud, Jean-François Longevial, Pascal Dumy, and Alberto Marra. "Synthesis and biological properties of multivalent iminosugars." New Journal of Chemistry 39, no. 7 (2015): 5050–74. http://dx.doi.org/10.1039/c5nj00462d.

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38

Ghavami, Ahmad, Blair D. Johnston, Matthew D. Maddess, Sarah M. Chinapoo, Morten T. Jensen, Birte Svensson, and B. Mario Pinto. "Synthesis of 1,4-anhydro-D-xylitol heteroanalogues of the naturally occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors." Canadian Journal of Chemistry 80, no. 8 (August 1, 2002): 937–42. http://dx.doi.org/10.1139/v02-078.

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The syntheses of two 1,4-anhydro-D-xylitol heteroanalogues (8 and 9) of the naturally occurring sulfonium ion, salacinol (3), containing a sulfur or nitrogen atom in the ring are described. Salacinol (3) is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of Type 2 diabetes. The synthetic strategy relies on the nucleophilic attack of sulfur or nitrogen analogues of 1,4-anhydro-D-xylitol at the least-hindered carbon of 2,4-O-benzylidene-L-erythritol-1,3-cyclic sulfate. The sulfonium ion 8 inhibited barley-α-amylase (AMY1) and porcine pancreatic-α-amylase (PPA), with Ki values of 109 ± 11 and 55 ± 5 µM, respectively. In contrast, the ammonium ion 9 showed no significant inhibition of either AMY1 or PPA. Compounds 8 and 9 also showed no significant inhibition of glucoamylase.Key Words: glycosidase inhibitors, salacinol analogues, anhydro-D-xylitol heteroanalogues, enzyme inhibition.

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39

M. Jespersen, Tina, Mikael Bols, Michael R. Sierks, and Troels Skrydstrup. "Synthesis of isofagomine, a novel glycosidase inhibitor." Tetrahedron 50, no. 47 (January 1994): 13449–60. http://dx.doi.org/10.1016/s0040-4020(01)89351-0.

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NISHIMURA, Yoshio. "The Synthesis and Biological Activity of Glycosidase Inhibitors." Journal of Synthetic Organic Chemistry, Japan 49, no. 9 (1991): 846–57. http://dx.doi.org/10.5059/yukigoseikyokaishi.49.846.

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41

Ogawa, Seiichiro, and Miki Kanto. "Design and Synthesis of 5a-Carbaglycopyranosylamime Glycosidase Inhibitors." Current Topics in Medicinal Chemistry 9, no. 1 (January 1, 2009): 58–75. http://dx.doi.org/10.2174/156802609787354324.

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42

Trapero, Ana, Meritxell Egido-Gabás, Jordi Bujons, and Amadeu Llebaria. "Synthesis and Evaluation of Hydroxymethylaminocyclitols as Glycosidase Inhibitors." Journal of Organic Chemistry 80, no. 7 (March 16, 2015): 3512–29. http://dx.doi.org/10.1021/acs.joc.5b00133.

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43

Baran, Arif, and Metin Balci. "Stereoselective Synthesis of Bishomo-inositols as Glycosidase Inhibitors." Journal of Organic Chemistry 74, no. 1 (January 2, 2009): 88–95. http://dx.doi.org/10.1021/jo801344f.

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44

Aguilar-Moncayo, Matilde, Carmen Ortiz Mellet, José M. García Fernández, and M. Isabel García-Moreno. "Synthesis of Thiohydantoin-Castanospermine Glycomimetics as Glycosidase Inhibitors." Journal of Organic Chemistry 74, no. 9 (May 2009): 3595–98. http://dx.doi.org/10.1021/jo900231b.

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45

Doddi, Venkata Ramana, Pavan K. Kancharla, Y. Suman Reddy, Amit Kumar, and Yashwant D. Vankar. "Synthesis of fused pyran-carbahexopyranoses as glycosidase inhibitors." Carbohydrate Research 344, no. 5 (March 2009): 606–12. http://dx.doi.org/10.1016/j.carres.2009.01.017.

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46

Liu, Hui, and B. Mario Pinto. "Design and synthesis of selenonium and sulfonium ions related to the naturally occurring glucosidase inhibitor salacinol." Canadian Journal of Chemistry 84, no. 10 (October 1, 2006): 1351–62. http://dx.doi.org/10.1139/v06-100.

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Four series of analogues of the naturally occurring glucosidase inhibitor salacinol were synthesized for structure–activity studies with different glycosidase enzymes. The target zwitterionic compounds were synthesized by means of nucleophilic attack at the least-hindered carbon atom of the 1,3-cyclic sulfates derived from D-glucose and D-mannose by the isopropylidene-protected 1,4-anhydro-4-thio- and seleno-D-allitols and the 4-thio- and seleno-L-allitols. Deprotection of the coupled products afforded the novel sulfonium and selenonium ions containing polyhy droxylated acyclic chains of four and six carbons, with different stereochemistry at the stereogenic centers and with 1,4-anhydro-4-seleno or 4-thio-D- or L- alditol heterocyclic rings. The compounds showed no significant activity against recombinant human maltase glucoamylase (MGA), a critical intestinal glucosidase involved in the processing of oligosaccharides of glucose into glucose itself.Key words: glycosidase inhibitors, zwitterionic, selenonium salts, sulfonium salts, cyclic sulfates, L-ascorbic acid, D-gulonic-γ-lactone.

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MEHTA, S., J. S. ANDREWS, B. D. JOHNSTON, B. SVENSSON, and B. M. PINTO. "ChemInform Abstract: Synthesis and Enzyme Inhibitory Activity of Novel Glycosidase Inhibitors Containing Sulfur and Selenium." ChemInform 27, no. 5 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199605249.

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Yang, Lin-Feng, Yuna Shimadate, Atsushi Kato, Yi-Xian Li, Yue-Mei Jia, George W. J. Fleet, and Chu-Yi Yu. "Synthesis and glycosidase inhibition of N-substituted derivatives of 1,4-dideoxy-1,4-imino-d-mannitol (DIM)." Organic & Biomolecular Chemistry 18, no. 5 (2020): 999–1011. http://dx.doi.org/10.1039/c9ob02029b.

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Jain, Vipin Kumar. "Divergent Synthesis of Various 2-Aryl Iminocyclitols from (R)-p-Hydroxyphenylglycine." Synthesis 51, no. 24 (September 30, 2019): 4635–44. http://dx.doi.org/10.1055/s-0037-1610729.

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A concise and efficient synthesis of various 2-aryl iminocyclitols is reported from (R)-p-hydroxyphenylglycine using Upjohn dihydroxylation and base-promoted intramolecular cyclization. These 2-aryl iminocyclitols are the important structural framework of various bioactive compounds and also known as glycosidase inhibitors.

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Csuk, René, Erik Prell, Stefan Reißmann, and Claudia Korb. "First Total Synthesis of a Fluorinated Calystegin." Zeitschrift für Naturforschung B 65, no. 4 (April 1, 2010): 445–51. http://dx.doi.org/10.1515/znb-2010-0402.

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A straightforward chiral pool synthesis for the first fluorinated calystegin is described. Key steps of this synthesis include an ultrasound-assisted Zn-mediated tandem ring opening reaction followed by a Grubbs’ catalyst-mediated ring closure metathesis reaction. The target compound is a selective and competitive inhibitor for a β -glycosidase.

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