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Journal articles on the topic 'Aminocyclitols'

Author: Grafiati

Published: 4 June 2021

Last updated: 7 September 2023

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1

Walker, James B. "Enzymatic Synthesis of Aminoglycoside Antibiotics: Novel Adenosylmethionine:2-Deoxystreptamine N-Methyltransferase Activities in Hygromycin B- and Spectinomycin-Producing Streptomyces spp. and Uses of the Methylated Products." Applied and Environmental Microbiology 68, no. 5 (2002): 2404–10. http://dx.doi.org/10.1128/aem.68.5.2404-2410.2002.

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ABSTRACT Aminocyclitols structurally related to streptamine, a 1,3-diaminocyclitol, are common components of the RNA-binding aminoglycoside antibiotics. The respective aminocyclitol cores of hygromycin B and spectinomycin are N 3-methyl-2-deoxy-d-streptamine and N 1,N 3-dimethyl-2-epi-streptamine. Adenosyl[methyl-14C]methionine:2-deoxystreptamine N-methyltransferase activities were detected in extracts of early-stationary-phase mycelia of the hygromycin B producer Streptomyces hygroscopicus subsp. hygroscopicus ATCC 27438 and the spectinomycin producer Streptomyces flavopersicus ATCC 19756. Ex

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2

Diaz, L., and A. Delgado. "Medicinal Chemistry of Aminocyclitols." Current Medicinal Chemistry 17, no. 22 (2010): 2393–418. http://dx.doi.org/10.2174/092986710791698512.

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3

Trost, Barry M., and Sushant Malhotra. "Asymmetric Stereodivergent Strategy Towards Aminocyclitols." Chemistry - A European Journal 20, no. 27 (2014): 8288–92. http://dx.doi.org/10.1002/chem.201402175.

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4

Braun, H. "Synthesis of chiral aminocyclitols via epoxyepimination." Tetrahedron: Asymmetry 1, no. 6 (1990): 395–402. http://dx.doi.org/10.1016/s0957-4166(00)82400-3.

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5

Alegret, Carlos, Jordi Benet-Buchholz, and Antoni Riera. "Stereodivergent Syntheses of Conduramines and Aminocyclitols." Organic Letters 8, no. 14 (2006): 3069–72. http://dx.doi.org/10.1021/ol061022e.

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6

Braun, H., W. Burger, G. Kresze, F. P. Schmidtchen, J. L. Vaerman, and H. G. Viehe. "Synthesis of chiral aminocyclitols via epoxyepimination." Tetrahedron: Asymmetry 1, no. 6 (1990): 403–15. http://dx.doi.org/10.1016/0957-4166(90)90041-8.

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7

Egido-Gabás, Meritxell, Pedro Serrano, Josefina Casas, Amadeu Llebaria, and Antonio Delgado. "New aminocyclitols as modulators of glucosylceramide metabolism." Org. Biomol. Chem. 3, no. 7 (2005): 1195–201. http://dx.doi.org/10.1039/b411473f.

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8

Trost, Barry M., and Sushant Malhotra. "ChemInform Abstract: Asymmetric Stereodivergent Strategy Towards Aminocyclitols." ChemInform 45, no. 52 (2014): no. http://dx.doi.org/10.1002/chin.201452056.

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9

Delgado, Antonio. "Recent Advances in the Chemistry of Aminocyclitols." European Journal of Organic Chemistry 2008, no. 23 (2008): 3893–906. http://dx.doi.org/10.1002/ejoc.200800238.

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10

Ho, Y. "In-vitro activities of aminoglycoside-aminocyclitols against mycobacteria." Journal of Antimicrobial Chemotherapy 40, no. 1 (1997): 27–32. http://dx.doi.org/10.1093/jac/40.1.27.

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11

Letellier, Philippe, Robert Ralainirina, Daniel Beaupère, and Raoul Uzan. "Synthesis of new aminocyclitols as potent enzymatic inhibitors." Tetrahedron Letters 35, no. 26 (1994): 4555–58. http://dx.doi.org/10.1016/s0040-4039(00)60726-8.

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12

Salamci, Emine. "Recent developments concerned with the synthesis of aminocyclitols." Tetrahedron Letters 61, no. 15 (2020): 151728. http://dx.doi.org/10.1016/j.tetlet.2020.151728.

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13

Zarga, Musa H. Abu, Taleb H. Al-Telb, and Wolfgang Voelter. "Notizen: Synthesis of 3-Amino-3-deoxy Sugars through Intramolecular Carbamate Cyclizations on a Neighbouring Oxirane Ring." Zeitschrift für Naturforschung B 50, no. 4 (1995): 697–98. http://dx.doi.org/10.1515/znb-1995-0440.

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3-Amino-3-deoxy sugars [1] are essential substructures of a wide variety of biologically active natural products exemplified in aminocyclitols, [2] macrolides [3] or anthracyclin antibiotics [4], With this respect, the transformations of common and readily available carbohydrates are of special interest. In this communication we want to line out a short route for the incorporation of a vicinal cis hydroxyl-amino function in the pyranose moiety.

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14

Trapero, Ana, Meritxell Egido-Gabás, and Amadeu Llebaria. "Adamantane substituted aminocyclitols as pharmacological chaperones for Gaucher disease." MedChemComm 4, no. 12 (2013): 1584. http://dx.doi.org/10.1039/c3md00217a.

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15

Wong, S., and LE Bryan. "Accumulation of Trospectomycin by Strains ofSalmonella typhimurium, escherichia coliandHaemophilus influenzae." Canadian Journal of Infectious Diseases 1, no. 2 (1990): 51–56. http://dx.doi.org/10.1155/1990/258273.

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Trospectomycin, unlike aminoglycosidic aminocyclitols, is accumulated by a nonsaturable, energy-independent, diffusional process inSalmonella typhimurium, Escherichia coliandHaemophilus influenzae.A deep rough mutant ofS typhimuriumwas more susceptible and accumulated the drug faster, and F porin deficient mutants ofE coliwere more resistant than parental strains. Trospectomycin likely uses both porin and nonporin pathways to cross the outer membrane. AnE colistrain effectively accumulated the drug anaerobically, explaining its anaerobic activity. AnH influenzaestrain accumulated trospectomyci

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16

Carless, Howard A. J., and Shahnaz S. Malik. "Enantiospecific synthesis of C-methyl azidoinositols and aminocyclitols from toluene." Tetrahedron: Asymmetry 3, no. 9 (1992): 1135–38. http://dx.doi.org/10.1016/s0957-4166(00)82095-9.

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17

Schürrle, Karsten, Barbara Beier, Oleg Werbitzky, and Wolfgang Piepersberg. "The methyl ester as a protective group: synthesis of aminocyclitols." Carbohydrate Research 212 (June 1991): 321–25. http://dx.doi.org/10.1016/0008-6215(91)84073-n.

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18

LETELLIER, P., R. RALAINIRINA, D. BEAUPERE, and R. UZAN. "ChemInform Abstract: Synthesis of New Aminocyclitols as Potent Enzymatic Inhibitors." ChemInform 25, no. 47 (2010): no. http://dx.doi.org/10.1002/chin.199447221.

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19

BAKKER, E. P. "Aminoglycoside and aminocyclitol antibiotics: hygromycin B is an atypical bactericidal compound that exerts effects on cells of Escherichia coli characteristic for bacteriostatic aminocyclitols." Journal of General Microbiology 138, no. 3 (1992): 563–69. http://dx.doi.org/10.1099/00221287-138-3-563.

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20

Donaldson, William A. "Recent progress in the synthesis of six-membered aminocyclitols (2008-2017)." Arkivoc 2018, no. 4 (2018): 231–56. http://dx.doi.org/10.24820/ark.5550190.p010.450.

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21

Shih, Tzenge-Lien, Heng-Yi Li, Ming-Shin Ke, and Wei-Shen Kuo. "Synthesis of a New Family of Aminocyclitols from D-(-)-Quinic Acid." Synthetic Communications 38, no. 23 (2008): 4139–49. http://dx.doi.org/10.1080/00397910802281429.

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22

Ogawa, Seiichiro, and Yasushi Shibata. "Synthesis of dl-penta-N,O-acetylvaliolamine and related branched-chain aminocyclitols." Carbohydrate Research 148, no. 2 (1986): 257–63. http://dx.doi.org/10.1016/s0008-6215(00)90393-8.

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23

Delgado, Antonio, Miroslav Sisa, Ana Trapero, and Amadeu Llebaria. "Small-Scale One-Pot Reductive Alkylation of Unprotected Aminocyclitols with Supported Reagents." Synthesis 2008, no. 19 (2008): 3167–70. http://dx.doi.org/10.1055/s-2008-1067258.

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24

ANGELAUD, R., Y. LANDAIS, and K. SCHENK. "ChemInform Abstract: Asymmetric Amino-Hydroxylation of Dienylsilanes. An Efficient Route to Aminocyclitols." ChemInform 28, no. 24 (2010): no. http://dx.doi.org/10.1002/chin.199724215.

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25

CARLESS, H. A. J., and S. S. MALIK. "ChemInform Abstract: Enantiospecific Synthesis of C-Methyl Azidoinositols and Aminocyclitols from Toluene." ChemInform 24, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199301258.

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26

Egido-Gabás, Meritxell, Daniel Canals, Josefina Casas, Amadeu Llebaria, and Antonio Delgado. "Aminocyclitols as Pharmacological Chaperones for Glucocerebrosidase, a Defective Enzyme in Gaucher Disease." ChemMedChem 2, no. 7 (2007): 992–94. http://dx.doi.org/10.1002/cmdc.200700061.

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27

Urumova, Valentina, Mihni Lyutskanov, and Vladi Petrov. "INVESTIGATIONS ON THE RESISTANCE OF COMMENSAL SWINE ESCHERICHIA COLI TO SOME AMINOGLYCOSIDES-AMINOCYCLITOLS." Archives of Veterinary Medicine 8, no. 1 (2016): 13–26. http://dx.doi.org/10.46784/e-avm.v8i1.102.

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Th e aim of this study was to describe the prevalence of antibiotic resistance to some aminoglycosides, streptomycin, spectinomycin and gentamicinand three aminoglycoside- resistance genes in Escherichia coli isolated from feces and lagoon manure in six swine farms in Republic of Bulgaria. Atotal of 274 E. coli isolates from 270 fecal samples and twelve samples from lagoon manure were tested by disk diff usion method to determine resistance patterns to 11 antimicrobial agents. Aminoglycosides resistance also was determined by E-test, agar dilution method, PCR and qPCR. Th e highest resistance

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28

Agami, Claude, François Couty, and Nicolas Rabasso. "Ring-closing metathesis of diolefinic oxazolidinones: a new access to tropanes and aminocyclitols." Tetrahedron Letters 42, no. 28 (2001): 4633–35. http://dx.doi.org/10.1016/s0040-4039(01)00830-9.

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29

Asamizu, Shumpei. "Biosynthesis of nitrogen-containing natural products, C7N aminocyclitols and bis-indoles, from actinomycetes." Bioscience, Biotechnology, and Biochemistry 81, no. 5 (2017): 871–81. http://dx.doi.org/10.1080/09168451.2017.1281726.

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30

Delgado, Antonio. "Recent Advances in the Chemistry of Aminocyclitols (Eur. J. Org. Chem. 23/2008)." European Journal of Organic Chemistry 2008, no. 23 (2008): 3883. http://dx.doi.org/10.1002/ejoc.200890060.

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31

Sander, Peter, Burkhard Springer, Therdsak Prammananan, et al. "Fitness Cost of Chromosomal Drug Resistance-Conferring Mutations." Antimicrobial Agents and Chemotherapy 46, no. 5 (2002): 1204–11. http://dx.doi.org/10.1128/aac.46.5.1204-1211.2002.

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ABSTRACT To study the cost of chromosomal drug resistance mutations to bacteria, we investigated the fitness cost of mutations that confer resistance to different classes of antibiotics affecting bacterial protein synthesis (aminocyclitols, 2-deoxystreptamines, macrolides). We used a model system based on an in vitro competition assay with defined Mycobacterium smegmatis laboratory mutants; selected mutations were introduced by genetic techniques to address the possibility that compensatory mutations ameliorate the resistance cost. We found that the chromosomal drug resistance mutations studie

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32

Harada, Shinji, Kexin Li, Ryuto Kino, et al. "Construction of Optically Active Isotwistanes and Aminocyclitols Using Chiral Cyclohexadiene as a Common Intermediate." Chemical and Pharmaceutical Bulletin 64, no. 10 (2016): 1474–83. http://dx.doi.org/10.1248/cpb.c16-00431.

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33

Kang, Kai, Chengyou Kan, Yi Du, Deshan Liu, and Anthony Yeung. "Immobilization of aminoglycosidic aminocyclitols antibiotic onto soap-free poly(MMA-EA-AA) latex particles." Journal of Biomaterials Science, Polymer Edition 17, no. 1-2 (2006): 91–101. http://dx.doi.org/10.1163/156856206774879081.

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34

Griffen, Julia A., Jenifer C. White, Gabriele Kociok-Köhn, et al. "New aminocyclitols with quaternary stereocentres via acylnitroso cycloaddition with an ipso,ortho arene dihydrodiol." Tetrahedron 69, no. 29 (2013): 5989–97. http://dx.doi.org/10.1016/j.tet.2013.04.033.

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35

Gravier-Pelletier, Christine, William Maton, Thierry Dintinger, Charles Tellier, and Yves Le Merrer. "Synthesis and glycosidase inhibitory activity of aminocyclitols with a C6- or a C7-ring." Tetrahedron 59, no. 44 (2003): 8705–20. http://dx.doi.org/10.1016/j.tet.2003.09.049.

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36

Díaz, Lucía, Jordi Bujons, Antonio Delgado, Hugo Gutiérrez-de-Terán та Johan Åqvist. "Computational Prediction of Structure−Activity Relationships for the Binding of Aminocyclitols to β-Glucocerebrosidase". Journal of Chemical Information and Modeling 51, № 3 (2011): 601–11. http://dx.doi.org/10.1021/ci100453a.

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37

Gupta, Preeti, A. P. John Pal, Y. Suman Reddy, and Yashwant D. Vankar. "Synthesis of Aminocyclitols and Trihydroxylated Indolizidinone from a D-Mannitol-Derived Common Building Block." European Journal of Organic Chemistry 2011, no. 6 (2010): 1166–75. http://dx.doi.org/10.1002/ejoc.201001171.

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38

Aydin, Gökay, Khamis Ally, Fatih Aktaş, Ertan Şahin, Arif Baran та Metin Balci. "Synthesis and α-Glucosidase and α-Amylase Inhibitory Activity Evaluation of Azido- and Aminocyclitols". European Journal of Organic Chemistry 2014, № 31 (2014): 6903–17. http://dx.doi.org/10.1002/ejoc.201402762.

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39

Díaz, Lucía, Jordi Bujons, Josefina Casas, Amadeu Llebaria, and Antonio Delgado. "Click Chemistry Approach to New N-Substituted Aminocyclitols as Potential Pharmacological Chaperones for Gaucher Disease†." Journal of Medicinal Chemistry 53, no. 14 (2010): 5248–55. http://dx.doi.org/10.1021/jm100198t.

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40

Agami, Claude, Francois Couty, and Nicolas Rabasso. "ChemInform Abstract: Ring-Closing Metathesis of Diolefinic Oxazolidinones: A New Access to Tropanes and Aminocyclitols." ChemInform 32, no. 40 (2010): no. http://dx.doi.org/10.1002/chin.200140220.

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41

Shih, Tzenge-Lien, and Shu-Yu Yang. "Regioselectivity in the Ring Opening of Epoxides for the Synthesis of Aminocyclitols from D-(-)-Quinic Acid." Molecules 17, no. 4 (2012): 4498–507. http://dx.doi.org/10.3390/molecules17044498.

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42

Sureshan, Kana M., Kyoko Ikeda, Naoki Asano, and Yutaka Watanabe. "Efficient syntheses of optically pure chiro- and allo-inositol derivatives, azidocyclitols and aminocyclitols from myo-inositol." Tetrahedron 64, no. 18 (2008): 4072–80. http://dx.doi.org/10.1016/j.tet.2008.02.032.

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43

Gómez, Ana M., Eduardo Moreno, Clara Uriel, Slawomir Jarosz, Serafín Valverde, and J. Cristóbal López. "Novel strategies for the preparation of aminocarbasugar analogues: syntheses of N-substituted aminocyclitols from d-mannose." Tetrahedron: Asymmetry 16, no. 14 (2005): 2401–7. http://dx.doi.org/10.1016/j.tetasy.2005.05.033.

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44

El Blidi, Lahssen, Mustapha Ahbala, Jean Bolte, and Marielle Lemaire. "Straightforward chemo-enzymatic synthesis of new aminocyclitols, analogues of valiolamine and their evaluation as glycosidase inhibitors." Tetrahedron: Asymmetry 17, no. 18 (2006): 2684–88. http://dx.doi.org/10.1016/j.tetasy.2006.09.010.

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45

Široký, Michael, Jozef Gonda, Miroslava Martinková, et al. "Synthesis and mannosidase inhibitory profile of a small library of aminocyclitols from shikimic acid-derived scaffolds." Carbohydrate Research 493 (July 2020): 108027. http://dx.doi.org/10.1016/j.carres.2020.108027.

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46

Patti, Angela, Claudia Sanfilippo, Mario Piattelli, and Giovanni Nicolosi. "Enzymatic desymmetrisation of conduritol D. preparation of homochiral intermediates for the synthesis of cyclitols and aminocyclitols." Tetrahedron: Asymmetry 7, no. 9 (1996): 2665–70. http://dx.doi.org/10.1016/0957-4166(96)00342-4.

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47

Ji, Li, Guo-Quan Zhou, Chao Qian, and Xin-Zhi Chen. "Synthesis of 1,2,3-Triazoles from Azide-Derivatised Aminocyclitols by Catalytic Diazo Transfer and CuAAC Click Chemistry." European Journal of Organic Chemistry 2014, no. 17 (2014): 3622–36. http://dx.doi.org/10.1002/ejoc.201301874.

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48

Sellier, Odile, Pierre Van de Weghe, Didier Le Nouen, Christiane Strehler, and Jacques Eustache. "Ring closing metathesis as an efficient approach to branched cyclitols and aminocyclitols: a short synthesis of valiolamine." Tetrahedron Letters 40, no. 5 (1999): 853–56. http://dx.doi.org/10.1016/s0040-4039(98)02539-8.

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49

Achary, Raghavendra, Hyeong Rae Kim, and Hyeon-Kyu Lee. "Stereoselective Synthesis of Highly Functionalized 5- and 6-Membered Aminocyclitols Starting with a Readily Available 2-Azetidinone." Journal of Organic Chemistry 84, no. 7 (2019): 4263–72. http://dx.doi.org/10.1021/acs.joc.9b00239.

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50

ElâBlidi, Lahssen, Zeinab Assaf, Flora CampsâBres, et al. "Fructose-1,6-Bisphosphate Aldolase-Mediated Synthesis of Aminocyclitols (Analogues of Valiolamine) and their Evaluation as Glycosidase Inhibitors." ChemCatChem 1, no. 4 (2009): 463–71. http://dx.doi.org/10.1002/cctc.200900151.

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