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Journal articles on the topic 'Galactofuranosides'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Predescu, Nicoleta Florentina, Silvia Iga, Alina Nicolescu, and Dumitru Petru Iga. "Koenigs-Knorr Synthesis of Galactofuranosides of Estrone, Androstanolone, 11a-Hydroxyprogesterone and Prednisolone." Revista de Chimie 59, no. 1 (2008): 52–55. http://dx.doi.org/10.37358/rc.08.1.1706.

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Galactofuranosylation has been accomplished with 1-bromo-1-deoxy-2,3,5,6-tetra-O-benzoyl-a-D-galactofuranoside in the presence of cadmium carbonate as promotor. Glycosylation agent has been prepared by bromination of penta-O-benzoyl-ab-D-galactofuranoside with a solution of hydrogen bromide in glacial acetic acid. The precursor of the latter reaction has been produced by benzoylation of D-galactose that had been heated in pyridine while still warm. The following hydroxysteroids have been selected as being representative in terms of configuration, type of hybridization of carbon bearing hydroxy

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2

Completo, Gladys C., Reymart V. Sangalang, Beatrice M. I. Pique, and Ruel C. Nacario. "Simple and Efficient Method for the Synthesis of Galactofuranosides." KIMIKA 27, no. 2 (2017): 38–49. http://dx.doi.org/10.26534/kimika.v27i2.38-49.

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An efficient and improved one-pot method for the synthesis of galactofuranosides via iodine-promoted cyclization of galactose diethyl dithioacetal in the presence of alcohol, acting both as solvent and nucleophile, is described. The reaction is carried out at room temperature. Alcohols, such as methanol, cyclohexanol and tert-butanol, were used as nucleophiles for the reaction using 2%, 3% and 5% iodine promoter, respectively. A key finding in this study was that the iodine-promoted cyclization of galactose diethyl dithioacetal with alcohol led to selective formation of β-galactofuranoside all

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3

Marino, C., K. Marino, L. Miletti, M. J. Manso Alves, W. Colli, and R. M. de Lederkremer. "1-Thio- -D-galactofuranosides: synthesis and evaluation as -D-galactofuranosidase inhibitors." Glycobiology 8, no. 9 (1998): 901–4. http://dx.doi.org/10.1093/glycob/8.9.901.

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4

Mariño, Karina, Carla Marino та Rosa M. de Lederkremer. "Specific Tritium Labeling of β--Galactofuranosides at the 6-Position: A Tool for β--Galactofuranosidase Detection". Analytical Biochemistry 301, № 2 (2002): 325–28. http://dx.doi.org/10.1006/abio.2001.5508.

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5

Bordoni, Andrea, Rosa M. de Lederkremer та Carla Marino. "Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases". Bioorganic & Medicinal Chemistry 18, № 14 (2010): 5339–45. http://dx.doi.org/10.1016/j.bmc.2010.05.038.

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6

Frigell, Jens, and Ian Cumpstey. "Synthesis of carbadisaccharide mimics of galactofuranosides." Tetrahedron Letters 50, no. 36 (2009): 5142–44. http://dx.doi.org/10.1016/j.tetlet.2009.06.115.

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7

Frigell, Jens, та Ian Cumpstey. "Carbasugar analogues of galactofuranosides: α-O-linked derivatives". Beilstein Journal of Organic Chemistry 6 (29 листопада 2010): 1127–31. http://dx.doi.org/10.3762/bjoc.6.129.

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Using an indirect method, we have synthesised α-linked carbasugar analogues of galactofuranosides for the first time. Ring opening of a β-talo configured carbasugar 1,2-epoxide by alcohol nucleophiles under Lewis acidic conditions proceeded with very good regioselectivity to give α-talo configured C1-substituted ethers with a free OH-group at the C2 position. Inversion of configuration at C2 by an oxidation–reduction sequence gave the α-galacto configured carbahexofuranose C1 ethers. A carbadisaccharide corresponding to the Galf(α1→3)Manp substructure from Apodus deciduus galactomannan was syn

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8

Mariño, Karina, and Carla Marino. "Synthesis of heteroaryl 1-thio-ß-D-galactofuranosides and evaluation of their inhibitory activity towards a ß-D-galactofuranosidase." Arkivoc 2005, no. 12 (2006): 341–51. http://dx.doi.org/10.3998/ark.5550190.0006.c27.

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9

Suleman, Muhammad, Jean-Pierre Gangneux, Laurent Legentil, et al. "Alkyl Galactofuranosides Strongly Interact with Leishmania donovani Membrane and Provide Antileishmanial Activity." Antimicrobial Agents and Chemotherapy 58, no. 4 (2014): 2156–66. http://dx.doi.org/10.1128/aac.01350-13.

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ABSTRACTWe investigated thein vitroeffects of four alkyl-galactofuranoside derivatives, i.e., octyl-β-d-galactofuranoside (compound 1), 6-amino-β-d-galactofuranoside (compound 2), 6-N-acetamido-β-d-galactofuranoside (compound 3), and 6-azido-β-d-galactofuranoside (compound 4), onLeishmania donovani. Their mechanism of action was explored using electron paramagnetic resonance spectroscopy (EPR) and nuclear magnetic resonance (NMR), and ultrastructural alterations were analyzed by transmission electron microscopy (TEM). Compound 1 showed the most promising effects by inhibiting promastigote grow

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10

Masui, Seiji, Yoshiyuki Manabe, Kohtaro Hirao, et al. "Kinetically Controlled Fischer Glycosidation under Flow Conditions: A New Method for Preparing Furanosides." Synlett 30, no. 04 (2019): 397–400. http://dx.doi.org/10.1055/s-0037-1611643.

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Kinetically controlled Fischer glycosidation was achieved under flow conditions. β-Hydroxy-substituted sulfonic acid functionalized silica (HO-SAS) was used as an acid catalyst. This reaction directly converted aldohexoses into kinetically favored furanosides to enable the practical synthesis of furanosides. After optimization of the reaction temperature and residence time, glucofuranosides, galactofuranosides, and mannofuranosides were synthesized in good yields.

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11

Owen, David J., Robin J. Thomson, and Mark von Itzstein. "A convenient synthesis of C-galactofuranosylic compounds (C-galactofuranosides)." Carbohydrate Research 337, no. 21-23 (2002): 2017–22. http://dx.doi.org/10.1016/s0008-6215(02)00133-7.

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12

Lowary, T. "Synthesis and conformational analysis of arabinofuranosides, galactofuranosides and fructofuranosides." Current Opinion in Chemical Biology 7, no. 6 (2003): 749–56. http://dx.doi.org/10.1016/j.cbpa.2003.10.005.

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13

Bordoni, Andrea, Carlos Lima, Karina Mariño, Rosa M. de Lederkremer та Carla Marino. "Facile synthesis of methyl α- and β-d-[6-3H]galactofuranosides from d-galacturonic acid. Substrates for the detection of galactofuranosidases". Carbohydrate Research 343, № 10-11 (2008): 1863–69. http://dx.doi.org/10.1016/j.carres.2008.02.019.

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14

Bai, Yu, та Todd L. Lowary. "2,3-Anhydrosugars in Glycoside Bond Synthesis. Application to α-d-Galactofuranosides". Journal of Organic Chemistry 71, № 26 (2006): 9658–71. http://dx.doi.org/10.1021/jo061713o.

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15

Frigell, Jens, Jean A. Pearcey, Todd L. Lowary, and Ian Cumpstey. "Carbasugar Analogues of Galactofuranosides: Pseudodisaccharide Mimics of Fragments of Mycobacterial Arabinogalactan." European Journal of Organic Chemistry 2011, no. 7 (2011): 1367–75. http://dx.doi.org/10.1002/ejoc.201001380.

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16

Sandbhor, Mahendra, Milan Bhasin, Dean T. Williams, Margaret Hsieh, Shih-Hsiung Wu, and Wei Zou. "Synthesis of iminoalditol analogues of galactofuranosides and their activities against glycosidases." Carbohydrate Research 343, no. 17 (2008): 2878–86. http://dx.doi.org/10.1016/j.carres.2008.07.013.

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17

Richards, Michele R., Yu Bai, and Todd L. Lowary. "Comparison between DFT- and NMR-based conformational analysis of methyl galactofuranosides." Carbohydrate Research 374 (June 2013): 103–14. http://dx.doi.org/10.1016/j.carres.2013.03.030.

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18

Tuekam, Brigitte A., Yong-Il Park, Clifford J. Unkefer та John E. Gander. "Relationship of Exo-β-d-Galactofuranosidase Kinetic Parameters to the Number of Phosphodiesters in Penicillium fellutanum Peptidophosphogalactomannan: Enzyme Purification and Kinetics of Glycopeptide and Galactofuran Chain Hydrolysis". Applied and Environmental Microbiology 67, № 10 (2001): 4648–56. http://dx.doi.org/10.1128/aem.67.10.4648-4656.2001.

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ABSTRACT Extracellular Penicillium fellutanumexo-β-d-galactofuranosidase, with a mass of 70 kDa, was purified to apparent homogeneity. The enzyme was used to investigate the influence of phosphodiesters of the peptidophosphogalactomannans pP2GMii and pP25GMii(containing 2 and 25 phosphodiester residues, respectively, per mol of polymer) on the kinetic parameters of galactofuranosyl hydrolysis of these two polymers, of 1-O-methyl-β-d-galactofuranoside, and of two galactofuranooligosaccharides. The enzyme did not hydrolyze phosphorylated galactose residues of pP2GMii or pP25GMii. Thek cat/Km val

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19

Ferrières, Vincent, Jérôme Joutel, Rachel Boulch, Myriam Roussel, Loı̈c Toupet, and Daniel Plusquellec. "Sulfur atom configuration of sulfinyl galactofuranosides determines different reactivities in glycosylation reactions." Tetrahedron Letters 41, no. 29 (2000): 5515–19. http://dx.doi.org/10.1016/s0040-4039(00)00887-x.

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20

Vaugenot, Jeane, Abderrafek El Harras, Olivier Tasseau, et al. "6-Deoxy-6-fluoro galactofuranosides: regioselective glycosylation, unexpected reactivity, and anti-leishmanial activity." Organic & Biomolecular Chemistry 18, no. 7 (2020): 1462–75. http://dx.doi.org/10.1039/c9ob02596k.

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21

Mittal, A., and M. Ali. "ChemInform Abstract: Diterpenic Labdane Galactofuranosides from the Roots of Calotropis procera (Ait.) R. Br." ChemInform 44, no. 37 (2013): no. http://dx.doi.org/10.1002/chin.201337173.

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22

Frigell, Jens, Lars Eriksson та Ian Cumpstey. "Carbasugar analogues of galactofuranosides: β-O-linked derivatives and towards β-S-linked derivatives". Carbohydrate Research 346, № 11 (2011): 1277–90. http://dx.doi.org/10.1016/j.carres.2011.04.032.

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23

COUSIN, M. A., S. NOTERMANS, P. HOOGERHOUT та J. H. VAN BOOM. "Detection of β-galactofuranosidase production byPenicilliumandAspergillusspecies using 4-nitrophenyl β-D-galactofuranoside". Journal of Applied Bacteriology 66, № 4 (1989): 311–17. http://dx.doi.org/10.1111/j.1365-2672.1989.tb02484.x.

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24

Pathak, Ashish K., Vibha Pathak, William J. Suling та ін. "Studies on n-Octyl-5-(α-d-arabinofuranosyl)-β-d-galactofuranosides for Mycobacterial Glycosyltransferase Activity". Bioorganic & Medicinal Chemistry 10, № 4 (2002): 923–28. http://dx.doi.org/10.1016/s0968-0896(01)00343-1.

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25

Chlubnová, Ilona, Dominik Filipp, Vojtech Spiwok, et al. "Enzymatic synthesis of oligo-d-galactofuranosides and l-arabinofuranosides: from molecular dynamics to immunological assays." Organic & Biomolecular Chemistry 8, no. 9 (2010): 2092. http://dx.doi.org/10.1039/b926988f.

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26

Varela, Oscar, Carla Marino та Rosa M. de Lederkremer. "Synthesis of p-nitrophenyl β-d-galactofuranoside. A convenient substrate for β-galactofuranosidase". Carbohydrate Research 155 (листопад 1986): 247–51. http://dx.doi.org/10.1016/s0008-6215(00)90153-8.

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27

Rémond, Caroline, Richard Plantier-Royon, Nathalie Aubry та Michael J. O’Donohue. "An original chemoenzymatic route for the synthesis of β-d-galactofuranosides using an α-l-arabinofuranosidase". Carbohydrate Research 340, № 4 (2005): 637–44. http://dx.doi.org/10.1016/j.carres.2005.01.016.

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28

Notermans, S., G. H. Veeneman, C. W. E. M. van Zuylen, P. Hoogerhout та J. H. van Boom. "(1 → 5)-linked β-d-galactofuranosides are immunodominant in extracellular polysaccharides of Penicillium and Aspergillus species". Molecular Immunology 25, № 10 (1988): 975–79. http://dx.doi.org/10.1016/0161-5890(88)90003-x.

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29

Tefsen, Boris, Ellen L. Lagendijk, Joohae Park та ін. "Fungal α-arabinofuranosidases of glycosyl hydrolase families 51 and 54 show a dual arabinofuranosyl- and galactofuranosyl-hydrolyzing activity". Biological Chemistry 393, № 8 (2012): 767–75. http://dx.doi.org/10.1515/hsz-2012-0134.

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Abstract Aspergillus niger possesses a galactofuranosidase activity, however, the corresponding enzyme or gene encoding this enzyme has never been identified. As evidence is mounting that enzymes exist with affinity for both arabinofuranose and galactofuranose, we investigated the possibility that α-l-arabinofuranosidases, encoded by the abfA and abfB genes, are responsible for the galactofuranosidase activity of A. niger. Characterization of the recombinant AbfA and AbfB proteins revealed that both enzymes do not only hydrolyze p-nitrophenyl-α-l-arabinofuranoside (pNp-α-Araf) but are also cap

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30

Marino, Carla, María J. Cancio, Oscar Varela та Rosa M. de Lederkremer. "Synthesis of 4-methylcoumarin-7-yl β-d-galactofuranoside, a fluorogenic substrate for galactofuranosidase". Carbohydrate Research 276, № 1 (1995): 209–13. http://dx.doi.org/10.1016/0008-6215(95)00239-p.

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31

de Talancé, Vincent Lemau, Emilie Thiery, Guillaume Eppe, Sandy El Bkassiny, Jérémie Mortier, and Stéphane P. Vincent. "A Simple Synthesis of D-Galactono-1,4-Lactone and Key Building Blocks for the Preparation of Galactofuranosides." Journal of Carbohydrate Chemistry 30, no. 7-9 (2011): 605–17. http://dx.doi.org/10.1080/07328303.2011.616273.

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32

Santra, Soumava, Emily Jonas, Jean-Paul Bourgault, Tarick El-Baba та Peter R. Andreana. "Kinetic Products Under Thermal Conditions: Rapid Entry into α/β-D-Galactofuranosides Using Microwave Irradiation and Selective Lewis Acids". Journal of Carbohydrate Chemistry 30, № 1 (2011): 27–40. http://dx.doi.org/10.1080/07328303.2011.585259.

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33

Baldoni, Luciana, and Carla Marino. "Synthesis of S- and C-galactofuranosides via a galactofuranosyl iodide. Isolable 1-galactofuranosylthiol derivative as a new glycosyl donor." Carbohydrate Research 362 (November 2012): 70–78. http://dx.doi.org/10.1016/j.carres.2012.08.021.

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34

MARINO, C., M. J. CANCIO, O. VARELA та R. M. DE LEDERKREMER. "ChemInform Abstract: Synthesis of 4-Methylcoumarin-7-yl β-D-Galactofuranoside, a Fluorogenic Substrate for Galactofuranosidase." ChemInform 27, № 8 (2010): no. http://dx.doi.org/10.1002/chin.199608229.

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35

Iwahara, Shojiro, Toshihiro Mishima, Nahrowi Ramli та Kaoru Takegawa. "Degradation ofβ1→6 Galactofuranoside Linkages in the Polysaccharide ofFusariumsp. M7-1 by Endo-β-galactofuranosidase fromBacillussp." Bioscience, Biotechnology, and Biochemistry 60, № 6 (1996): 957–61. http://dx.doi.org/10.1271/bbb.60.957.

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36

Santra, Soumava, Emily Jonas, Jean-Paul Bourgault, Tarick El-Baba та Peter R. Andreana. "ChemInform Abstract: Kinetic Products under Thermal Conditions: Rapid Entry into α/β-D-Galactofuranosides Using Microwave Irradiation and Selective Lewis Acids." ChemInform 43, № 14 (2012): no. http://dx.doi.org/10.1002/chin.201214191.

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37

Kovensky, José, and Pierre Sinaÿ. "Synthesis of Galactofuranosides by Regioselective Ring Opening of a 1,4-Anhydrogalactopyranose Derivative: A Possible Chemical Model for an Unprecedented Enzymatic Reaction." European Journal of Organic Chemistry 2000, no. 21 (2000): 3523–25. http://dx.doi.org/10.1002/1099-0690(200011)2000:21<3523::aid-ejoc3523>3.0.co;2-c.

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38

Kovensky, José, and Pierre Sinaÿ. "Synthesis of Galactofuranosides by Regioselective Ring Opening of a 1,4-Anhydrogalactopyranose Derivative: A Possible Chemical Model for an Unprecedented Enzymatic Reaction." European Journal of Organic Chemistry 2000, no. 24 (2000): 4125. http://dx.doi.org/10.1002/1099-0690(200012)2000:21<4125::aid-ejoc4125>3.0.co;2-l.

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39

Tilve, Mariano J., Carmen R. Cori та Carola Gallo-Rodriguez. "Regioselective 5-O-Opening of Conformationally Locked 3,5-O-Di-tert-butylsilylene-d-galactofuranosides. Synthesis of (1→5)-β-d-Galactofuranosyl Derivatives". Journal of Organic Chemistry 81, № 20 (2016): 9585–94. http://dx.doi.org/10.1021/acs.joc.6b01562.

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40

Lubineau, André, та Jean-Claude Fischer. "High-Yielding One-Step Conversion of D-Glucose and D-Galactose to the Corresponding α and β Methyl-D-glucofuranosides and Galactofuranosides". Synthetic Communications 21, № 6 (1991): 815–18. http://dx.doi.org/10.1080/00397919108019762.

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41

Kovensky, Jose, and Pierre Sinay. "ChemInform Abstract: Synthesis of Galactofuranosides by Regioselective Ring Opening of a 1,4-Anhydrogalactopyranose Derivative: A Possible Chemical Model for an Unprecedented Enzymatic Reaction." ChemInform 32, no. 6 (2001): no. http://dx.doi.org/10.1002/chin.200106167.

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42

Miletti, Luiz C., Carla Marino, Karina Mariño, Rosa M. de Lederkremer, Walter Colli та Maria Júlia M. Alves. "Immobilized 4-aminophenyl 1-thio-β-d-galactofuranoside as a matrix for affinity purification of an exo-β-d-galactofuranosidase". Carbohydrate Research 320, № 3-4 (1999): 176–82. http://dx.doi.org/10.1016/s0008-6215(99)00158-5.

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43

LUBINEAU, A., та J. C. FISCHER. "ChemInform Abstract: High-Yielding One-Step Conversion of D-Glucose and D-Galactose to the Corresponding α- and β-Methyl-D-glucofuranosides and Galactofuranosides." ChemInform 22, № 50 (2010): no. http://dx.doi.org/10.1002/chin.199150224.

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44

Shen, Lin, Albertus Viljoen, Sydney Villaume, et al. "The endogenous galactofuranosidase GlfH1 hydrolyzes mycobacterial arabinogalactan." Journal of Biological Chemistry 295, no. 15 (2020): 5110–23. http://dx.doi.org/10.1074/jbc.ra119.011817.

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Despite impressive progress made over the past 20 years in our understanding of mycolylarabinogalactan-peptidoglycan (mAGP) biogenesis, the mechanisms by which the tubercle bacillus Mycobacterium tuberculosis adapts its cell wall structure and composition to various environmental conditions, especially during infection, remain poorly understood. Being the central portion of the mAGP complex, arabinogalactan (AG) is believed to be the constituent of the mycobacterial cell envelope that undergoes the least structural changes, but no reports exist supporting this assumption. Herein, using recombi

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45

Seničar, Mateja, Pierre Lafite, Svetlana V. Eliseeva, Stéphane Petoud, Ludovic Landemarre, and Richard Daniellou. "Galactofuranose-Related Enzymes: Challenges and Hopes." International Journal of Molecular Sciences 21, no. 10 (2020): 3465. http://dx.doi.org/10.3390/ijms21103465.

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Galactofuranose is a rare form of the well-known galactose sugar, and its occurrence in numerous pathogenic micro-organisms makes the enzymes responsible for its biosynthesis interesting targets. Herein, we review the role of these carbohydrate-related proteins with a special emphasis on the galactofuranosidases we recently characterized as an efficient recombinant biocatalyst.

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46

Wallis, Gregg L. F., Frank W. Hemming, and John F. Peberdy. "Î²-Galactofuranoside glycoconjugates on conidia and conidiophores ofAspergillus niger." FEMS Microbiology Letters 201, no. 1 (2001): 21–27. http://dx.doi.org/10.1111/j.1574-6968.2001.tb10727.x.

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47

Iga, Dumitru Petru, Silvia Iga, Richard R. Schmidt та Maria-Cristina Buzas. "Chemical synthesis of cholesteryl β-d-galactofuranoside and -pyranoside". Carbohydrate Research 340, № 12 (2005): 2052–54. http://dx.doi.org/10.1016/j.carres.2005.06.015.

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48

Wallis, G. "β-Galactofuranoside glycoconjugates on conidia and conidiophores of Aspergillus niger". FEMS Microbiology Letters 201, № 1 (2001): 21–27. http://dx.doi.org/10.1016/s0378-1097(01)00219-1.

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49

Miletti, Luiz Claudio, Karina Mariño, Carla Marino, Walter Colli, Maria Julia Manso Alves та Rosa M. de Lederkremer. "Evidence for exo β-d-galactofuranosidase in Trypanosoma cruzi". Molecular and Biochemical Parasitology 127, № 1 (2003): 85–88. http://dx.doi.org/10.1016/s0166-6851(02)00307-9.

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50

Ramli, Nahrowi, Michiko Fujinaga, Mitsuaki Tabuchi, Kaoru Takegawa та Shojiro Iwahara. "Isolation and Characterization of a Novel Endo-β-galactofuranosidase fromBacillussp." Bioscience, Biotechnology, and Biochemistry 59, № 10 (1995): 1856–60. http://dx.doi.org/10.1271/bbb.59.1856.

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