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Journal articles on the topic 'Chitobiose'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Verma, Subhash Chandra, and Subramony Mahadevan. "ThechbGGene of the Chitobiose (chb) Operon of Escherichia coli Encodes a Chitooligosaccharide Deacetylase." Journal of Bacteriology 194, no. 18 (2012): 4959–71. http://dx.doi.org/10.1128/jb.00533-12.

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ABSTRACTThechboperon ofEscherichia coliis involved in the utilization of the β-glucosides chitobiose and cellobiose. The function ofchbG(ydjC), the sixth open reading frame of the operon that codes for an evolutionarily conserved protein is unknown. We show thatchbGencodes a monodeacetylase that is essential for growth on the acetylated chitooligosaccharides chitobiose and chitotriose but is dispensable for growth on cellobiose and chitosan dimer, the deacetylated form of chitobiose. The predicted active site of the enzyme was validated by demonstrating loss of function upon substitution of it

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2

Tilly, Kit, Abdallah F. Elias, Jennifer Errett, et al. "Genetics and Regulation of Chitobiose Utilization inBorrelia burgdorferi." Journal of Bacteriology 183, no. 19 (2001): 5544–53. http://dx.doi.org/10.1128/jb.183.19.5544-5553.2001.

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ABSTRACT Borrelia burgdorferi spends a significant proportion of its life cycle within an ixodid tick, which has a cuticle containing chitin, a polymer of N-acetylglucosamine (GlcNAc). TheB. burgdorferi celA, celB, andcelC genes encode products homologous to transporters for cellobiose and chitobiose (the dimer subunit of chitin) in other bacteria, which could be useful for bacterial nutrient acquisition during growth within ticks. We found that chitobiose efficiently substituted for GlcNAc during bacterial growth in culture medium. We inactivated the celB gene, which encodes the putative memb

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3

Sze, Ching Wooen, Alexis Smith, Young Hee Choi, et al. "Study of the Response Regulator Rrp1 Reveals Its Regulatory Role in Chitobiose Utilization and Virulence of Borrelia burgdorferi." Infection and Immunity 81, no. 5 (2013): 1775–87. http://dx.doi.org/10.1128/iai.00050-13.

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ABSTRACTLife cycle alternation between arthropod and mammals forces the Lyme disease spirochete,Borrelia burgdorferi, to adapt to different host milieus by utilizing diverse carbohydrates. Glycerol and chitobiose are abundantly present in theIxodestick.B. burgdorferican utilize glycerol as a carbohydrate source for glycolysis and chitobiose to produceN-acetylglucosamine (GlcNAc), a key component of the bacterial cell wall. A recent study reported that Rrp1, a response regulator that synthesizes cyclic diguanylate (c-di-GMP), governs glycerol utilization inB. burgdorferi. In this report, we fou

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4

Chen, An-Shu, Tadao Taguchi, Kazuo Sakai, Kazuaki Kikuchi, Min-Wei Wang, and Ichitomo Miwa. "Antioxidant Activities of Chitobiose and Chitotriose." Biological & Pharmaceutical Bulletin 26, no. 9 (2003): 1326–30. http://dx.doi.org/10.1248/bpb.26.1326.

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5

Yui, Toshifumi, Hisayoshi Kobayashi, Shinichi Kitamura, and Kiyohisa Imada. "Conformational analysis of chitobiose and chitosan." Biopolymers 34, no. 2 (1994): 203–8. http://dx.doi.org/10.1002/bip.360340206.

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6

Chen, Tong, Gong Cheng, Siming Jiao, et al. "Expression and Biochemical Characterization of a Novel Marine Chitosanase from Streptomyces niveus Suitable for Preparation of Chitobiose." Marine Drugs 19, no. 6 (2021): 300. http://dx.doi.org/10.3390/md19060300.

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It is known that bioactivities of chitooligosaccharide (COS) are closely related to the degree of polymerization (DP); therefore, it is essential to prepare COS with controllable DP, such as chitobiose showing high antioxidant and antihyperlipidemia activities. In this study, BLAST, sequence alignment and phylogenetic analysis of characterized glycoside hydrolase (GH) 46 endo-chitosanases revealed that a chitosanase Sn1-CSN from Streptomyces niveus was different from others. Sn1-CSN was overexpressed in E. coli, purified and characterized in detail. It showed the highest activity at pH 6.0 and

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7

Kuhn, P., and P. Van Roey. "Interaction of chitobiose with PNGase F mutants." Acta Crystallographica Section A Foundations of Crystallography 52, a1 (1996): C198. http://dx.doi.org/10.1107/s0108767396091428.

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8

Macdonald, James M, Chris A Tarling, Edward J Taylor, et al. "Chitinase Inhibition by Chitobiose and Chitotriose Thiazolines." Angewandte Chemie International Edition 49, no. 14 (2010): 2599–602. http://dx.doi.org/10.1002/anie.200906644.

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9

Macdonald, James M, Chris A Tarling, Edward J Taylor, et al. "Chitinase Inhibition by Chitobiose and Chitotriose Thiazolines." Angewandte Chemie 122, no. 14 (2010): 2653–56. http://dx.doi.org/10.1002/ange.200906644.

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10

Katiyar, Samiksha, E. J. M. Van Damme, Willy J. Peumans, and Avadhesha Surolia. "Thermodynamic Analysis of Chitooligosaccharide Binding to Urtica dioica agglutinin by Isothermal Titration Calorimetry." Bioscience Reports 19, no. 5 (1999): 411–19. http://dx.doi.org/10.1023/a:1020264206433.

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UDA (Urtica dioica agglutinin) contains two hevein like domains with two non-identical interacting sites and is specific for chitooligosaccharides. The binding of chitooligosaccharides to UDA was studied by Isothermal Titration Calorimetry. Each site is composed of three subsites, each binding to a sugar residue. Thermodynamic parameters obtained show that while chitobiose has two independent non-interacting sites, chitotriose, chitotetrose and chitopentose have two interacting sites on each monomer of UDA. Values of binding enthalpy (ΔH) increase almost by a factor of 7 in going from chitobio

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11

Berg, Gry Mine, Daniel J. Repeta, and Julie Laroche. "Dissolved Organic Nitrogen Hydrolysis Rates in Axenic Cultures of Aureococcus anophagefferens (Pelagophyceae): Comparison with Heterotrophic Bacteria." Applied and Environmental Microbiology 68, no. 1 (2002): 401–4. http://dx.doi.org/10.1128/aem.68.1.401-404.2002.

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ABSTRACT The marine autotroph Aureococcus anophagefferens (Pelagophyceae) was rendered axenic in order to investigate hydrolysis rates of peptides, chitobiose, acetamide, and urea as indicators of the ability to support growth on dissolved organic nitrogen. Specific rates of hydrolysis varied between 8 and 700% of rates observed in associated heterotrophic marine bacteria.

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12

Berg, Thorsten, Stefan Schild, and Joachim Reidl. "Regulation of the chitobiose–phosphotransferase system in Vibrio cholerae." Archives of Microbiology 187, no. 6 (2007): 433–39. http://dx.doi.org/10.1007/s00203-006-0207-4.

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13

Beckmann, Henning S. G., Heiko M. Möller, and Valentin Wittmann. "High-affinity multivalent wheat germ agglutinin ligands by one-pot click reaction." Beilstein Journal of Organic Chemistry 8 (June 1, 2012): 819–26. http://dx.doi.org/10.3762/bjoc.8.91.

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A series of six mono-, di-, and trivalent N,N’-diacetylchitobiose derivatives was conveniently prepared by employing a one-pot procedure for Cu(II)-catalyzed diazo transfer and Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) starting from commercially available amines. These glycoclusters were probed for their binding potencies to the plant lectin wheat germ agglutinin (WGA) from Triticum vulgaris by an enzyme-linked lectin assay (ELLA) employing covalently immobilized N-acetylglucosamine (GlcNAc) as a reference ligand. IC50 values were in the low micromolar/high nanomolar range, depending

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14

Morais, Latino Loureiro, Hideya Yuasa, Khalil Bennis, Isabelle Ripoche, and France-Isabelle Auzanneau. "Chemoenzymatic synthesis of thio-nod factor intermediates Enzymatic transfer of glucosamine on thiochitobiose derivatives." Canadian Journal of Chemistry 84, no. 4 (2006): 587–96. http://dx.doi.org/10.1139/v06-043.

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The chemoenzymatic syntheses of thioanalogues of nodulation factors in which the nonreducing end glucosamine residue is available for the introduction of the fatty acid moiety at the free NH2 group are reported. We are describing the chemical synthesis of UDP-GlcNH2 and its use in the enzymatic transfer of GlcNH2 by the bovine galactosyltransferase (EC 2.4.1.90) onto O-4 of the nonreducing end N-acetylglucosamine residues of chitobiose, thiochitobiose, and allyl thiochitobioside. The enzymatic reactions on chitobiose and thiochitobiose were followed by TLC and MALDI MS and showed about 50% con

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15

Yu, Biao, Qinqin Ouyang, Chuan Li та Yongzheng Hui. "The Tmsotf-Promoted “One Pot” β-Glycosidations of Peracetylated Chitobiose". Journal of Carbohydrate Chemistry 15, № 3 (1996): 297–302. http://dx.doi.org/10.1080/07328309608005654.

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16

SUNDIN, PETER, STEFAN OLSSON, and GORAN ODHAM. "Degradation of Chitotetraose to Chitobiose in the Axenic Rape Rhizosphere." Journal of Experimental Botany 42, no. 7 (1991): 931–34. http://dx.doi.org/10.1093/jxb/42.7.931.

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17

Kunz, Horst, and Carlo Unverzagt. "Schutzgruppenabhängige Stabilität von Intersaccharid-Bindungen – Synthese eines Fucosyl-Chitobiose-Glycopeptids." Angewandte Chemie 100, no. 12 (1988): 1763–65. http://dx.doi.org/10.1002/ange.19881001212.

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18

Harata, K., and R. Kanai. "Crystallographic evaluation of the motion of chitobiose bound to lysozyme." Seibutsu Butsuri 40, supplement (2000): S167. http://dx.doi.org/10.2142/biophys.40.s167_2.

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19

Rani, T. Swaroopa, Jogi Madhuprakash, and Appa Rao Podile. "Chitinase-E from Chitiniphilus shinanonensis generates chitobiose from chitin flakes." International Journal of Biological Macromolecules 163 (November 2020): 1037–43. http://dx.doi.org/10.1016/j.ijbiomac.2020.07.052.

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20

HONDA, Yuji, Motomitsu KITAOKA, and Kiyoshi HAYASHI. "Reaction mechanism of chitobiose phosphorylase from Vibrio proteolyticus: identification of family 36 glycosyltransferase in Vibrio." Biochemical Journal 377, no. 1 (2004): 225–32. http://dx.doi.org/10.1042/bj20031171.

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A family 36 glycosyltransferase gene was cloned from Vibrio proteolyticus. The deduced amino acid sequence showed a high degree of identity with ChBP (chitobiose phosphorylase) from another species, Vibrio furnissii. The recombinant enzyme catalysed the reversible phosphorolysis of (GlcNAc)2 (chitobiose) to form 2-acetamide-2-deoxy-α-d-glucose 1-phosphate [GlcNAc-1-P] and GlcNAc, but showed no activity on cellobiose, indicating that the enzyme was ChBP, not cellobiose phosphorylase. In the synthetic reaction, the ChBP was active with α-d-glucose 1-phosphate as the donor substrate as well as Gl

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21

Dao-Thi, M. H., P. Rizkallah, L. Wyns, F. Poortmans, and R. Loris. "Quaternary Structure of UEA-II, the Chitobiose Specific Lectin from Gorse." Acta Crystallographica Section D Biological Crystallography 54, no. 5 (1998): 844–47. http://dx.doi.org/10.1107/s0907444998001218.

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22

Chen, An-Shu, Tadao Taguchi, Hirokazu Okamoto, et al. "Pharmacokinetics of Chitobiose and Chitotriose Administered Intravenously or Orally to Rats." Biological & Pharmaceutical Bulletin 28, no. 3 (2005): 545–48. http://dx.doi.org/10.1248/bpb.28.545.

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23

YU, B., Q. OUYANG, C. LI та Y. HUI. "ChemInform Abstract: TmsOTf-Promoted “One Pot” β-Glycosidations of Peracetylated Chitobiose." ChemInform 27, № 36 (2010): no. http://dx.doi.org/10.1002/chin.199636216.

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24

Jo, Gyung-Hyun, Wan-Taek Ju, and Ro-Dong Park. "Biological production of chitobiose from crab shell waste by microbial fermentation." Journal of Biotechnology 136 (October 2008): S467. http://dx.doi.org/10.1016/j.jbiotec.2008.07.1087.

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25

Nishimura, Shin-Ichiro, Hiroyoshi Kuzuhara, Yasuyuki Takiguchi, and Kenzo Shimahara. "Peracetylated chitobiose: Preparation by specific degradations of chitin, and chemical manipulations." Carbohydrate Research 194 (December 1989): 223–31. http://dx.doi.org/10.1016/0008-6215(89)85021-9.

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26

Rohlenová, Anna, Miroslav Ledvina, David Šaman, and Karel Bezouška. "Synthesis of Linear and Branched Regioisomeric Chitooligosaccharides as Potential Mimetics of Natural Oligosaccharide Ligands of Natural Killer Cells NKR-P1 and CD69 Lectin Receptors." Collection of Czechoslovak Chemical Communications 69, no. 9 (2004): 1781–804. http://dx.doi.org/10.1135/cccc20041781.

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Regioisomer of chitobiose 13 with β(1→3) glycosidic bond and branched analog of chitotriose 25 having β(1→4) and β(1→3) glycosidic bonds, were prepared and tested as potential mimetics of natural oligosaccharide ligands for activating lectin receptors NKR-P1A and CD69 of natural killer (NK) cells. The structural requirements of NKR-P1 lectin receptor on effective mimetics of its natural ligands has been discussed. A significant binding activity of the branched trisaccharide 25 to the receptor CD69 was observed.

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27

Loveless, R. W., T. Feizi, R. A. Childs, et al. "Bovine serum conglutinin is a lectin which binds non-reducing terminal N-acetylglucosamine, mannose and fucose residues." Biochemical Journal 258, no. 1 (1989): 109–13. http://dx.doi.org/10.1042/bj2580109.

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Carbohydrate recognition by bovine serum conglutinin has been investigated by inhibition and direct binding assays using glycoproteins and polysaccharides from Saccharomyces cerevisiae (baker's yeast), and neoglycolipids derived from N-acetylglucosamine oligomers, mannobiose and human milk oligosaccharides. The results clearly show that conglutinin is a lectin which binds terminal N-acetylglucosamine, mannose and fucose residues as found in chitobiose (GlcNAc beta 1-4GlcNAc), mannobiose (Man alpha 1-3Man) and lacto-N-fucopentaose II [Fuc alpha 1-4(Gal beta 1-3)GlcNAc beta 1-3Gal beta 1-4Glc] r

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28

Shahgholi, Mona, Mark M. Ross, John H. Callahan, and Richard A. Smucker. "Electrospray Mass Spectrometric Detection of Chitobiose in Enzyme Hydrolysates of Marine Phytoplankton." Analytical Chemistry 68, no. 8 (1996): 1335–41. http://dx.doi.org/10.1021/ac951240d.

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29

Rhodes, Ryan G., Janet A. Atoyan, and David R. Nelson. "The chitobiose transporter, chbC, is required for chitin utilization in Borrelia burgdorferi." BMC Microbiology 10, no. 1 (2010): 21. http://dx.doi.org/10.1186/1471-2180-10-21.

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30

Rhodes, Ryan G., Wendy Coy, and David R. Nelson. "Chitobiose utilization in Borrelia burgdorferi is dually regulated by RpoD and RpoS." BMC Microbiology 9, no. 1 (2009): 108. http://dx.doi.org/10.1186/1471-2180-9-108.

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31

Witte, Martin D., Danielle Horst, Emmanuel J. H. J. Wiertz, Gijsbert A. van der Marel, and Herman S. Overkleeft. "Synthesis and Biological Evaluation of a Chitobiose-Based PeptideN-Glycanase Inhibitor Library." Journal of Organic Chemistry 74, no. 2 (2009): 605–16. http://dx.doi.org/10.1021/jo801906s.

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32

Ilankovan, Paraman, San Hein, Chuen-How Ng, Trang Si Trung, and Willem F. Stevens. "Production of N-acetyl chitobiose from various chitin substrates using commercial enzymes." Carbohydrate Polymers 63, no. 2 (2006): 245–50. http://dx.doi.org/10.1016/j.carbpol.2005.08.060.

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33

Li, Yubin, Yan Gou, Zhongchuan Liu, Tian Xie, and Ganggang Wang. "Structure-based rational design of chitosanase CsnMY002 for high yields of chitobiose." Colloids and Surfaces B: Biointerfaces 202 (June 2021): 111692. http://dx.doi.org/10.1016/j.colsurfb.2021.111692.

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34

Chen, An-Shu, Tadao Taguchi, Kazuo Sakai, Yoshiharu Matahira, Min-Wei Wang, and Ichitomo Miwa. "Effect of Chitobiose and Chitotriose on Carbon Tetrachloride-Induced Acute Hepatotoxicity in Rats." Biological & Pharmaceutical Bulletin 28, no. 10 (2005): 1971–73. http://dx.doi.org/10.1248/bpb.28.1971.

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35

Hojo, Hironobu, Jun Watabe, Yoshiaki Nakahara, et al. "Synthesis of the extracellular Ig domain I of Emmprin carrying a chitobiose unit." Tetrahedron Letters 42, no. 16 (2001): 3001–4. http://dx.doi.org/10.1016/s0040-4039(01)00342-2.

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36

Kunz, Horst, and Carlo Unverzagt. "Protecting-Group-Dependent Stability of Intersaccharide Bonds?Synthesis of a Fucosyl-Chitobiose Glycopeptide." Angewandte Chemie International Edition in English 27, no. 12 (1988): 1697–99. http://dx.doi.org/10.1002/anie.198816971.

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37

Wang, Meng, Feng Zheng, Ting Wang, et al. "Characterization of Stackebrandtia nassauensis GH 20 Beta-Hexosaminidase, a Versatile Biocatalyst for Chitobiose Degradation." International Journal of Molecular Sciences 20, no. 5 (2019): 1243. http://dx.doi.org/10.3390/ijms20051243.

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An unstudied β-N-acetylhexosaminidase (SnHex) from the soil bacterium Stackebrandtia nassauensis was successfully cloned and subsequently expressed as a soluble protein in Escherichia coli. Activity tests and the biochemical characterization of the purified protein revealed an optimum pH of 6.0 and a robust thermal stability at 50 °C within 24 h. The addition of urea (1 M) or sodium dodecyl sulfate (1% w/v) reduced the activity of the enzyme by 44% and 58%, respectively, whereas the addition of divalent metal ions had no effect on the enzymatic activity. PUGNAc (O-(2-acetamido-2-deoxy-D-glucop

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38

Kuroiwa, T., K. Kimura, S. Ichikawa, M. Nakajima, S. Sato, and S. Mukataka. "Lipase-Catalysed Synthesis of Fatty Acid Modified Chitobiose in a Low-Water Organic Solvent." Food and Bioproducts Processing 85, no. 2 (2007): 98–103. http://dx.doi.org/10.1205/fbp06049.

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39

Cao, Bobo, Jiuyao Du, Ziping Cao, Xuejun Sun, Haitao Sun та Hui Fu. "DFT study on the dissolution mechanisms of α-cyclodextrin and chitobiose in ionic liquid". Carbohydrate Polymers 169 (серпень 2017): 227–35. http://dx.doi.org/10.1016/j.carbpol.2017.04.012.

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40

Fang, Xinggao, Barbara S. Gibbs, and James K. Coward. "Synthesis and evaluation of synthetic analogues of dolichyl-P-P-chitobiose as oligosaccharyltransferase substrates." Bioorganic & Medicinal Chemistry Letters 5, no. 22 (1995): 2701–6. http://dx.doi.org/10.1016/0960-894x(95)00460-b.

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41

Egusa, Shizuka, Masahiro Goto, and Takuya Kitaoka. "Facile and direct synthesis of long-chain chitin from chitobiose via proton-assisted nonaqueous biocatalysis." Journal of Molecular Catalysis B: Enzymatic 87 (March 2013): 69–74. http://dx.doi.org/10.1016/j.molcatb.2012.10.005.

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42

Trimble, R. B., P. H. Atkinson, A. L. Tarentino, T. H. Plummer, F. Maley, and K. B. Tomer. "Transfer of glycerol by Endo-beta-N-acetylglucosaminidase F to oligosaccharides during chitobiose core cleavage." Journal of Biological Chemistry 261, no. 26 (1986): 12000–12005. http://dx.doi.org/10.1016/s0021-9258(18)67193-5.

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43

Wu, Yue-Jin, Chih-Yu Cheng, and Yaw-Kuen Li. "Cloning and Expression of Chitinase A fromSerratia Marcescensfor Large-Scale Preparation ofN,N-Diacetyl Chitobiose." Journal of the Chinese Chemical Society 56, no. 4 (2009): 688–95. http://dx.doi.org/10.1002/jccs.200900103.

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44

Sakamoto, Junji, and Shiro Kobayashi. "Enzymatic Synthesis of 3-O-Methylated Chitin Oligomers from New Derivatives of a Chitobiose Oxazoline." Chemistry Letters 33, no. 6 (2004): 698–99. http://dx.doi.org/10.1246/cl.2004.698.

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45

Sakamoto, Junji, Takeshi Watanabe, Yumiko Ariga, and Shiro Kobayashi. "Ring-Opening Glycosylation of a Chitobiose Oxazoline Catalyzed by a Non-Chitinolytic Mutant of Chitinase." Chemistry Letters 30, no. 11 (2001): 1180–81. http://dx.doi.org/10.1246/cl.2001.1180.

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46

H., Li, Morimoto K., Katagiri N. та ін. "A novel β- N -acetylglucosaminidase of Clostridium paraputrificum M-21 with high activity on chitobiose". Applied Microbiology and Biotechnology 60, № 4 (2002): 420–27. http://dx.doi.org/10.1007/s00253-002-1129-y.

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47

Flescher, E., Y. Keisari, J. Lengy, and D. Gold. "On the possible schistosomulicidal effect of macrophage-derived lysozyme." Parasitology 103, no. 1 (1991): 61–64. http://dx.doi.org/10.1017/s0031182000059291.

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Lysozyme secretion from macrophages of Schistosoma mansoni-infected mice was time dependent, rising significantly from the 8th week post-infection, the macrophages thereafter exhibiting very high levels (> 90%) of schistosomulicidal activity. Despite the ability of lysozyme to kill schistosomula in vitro, the concentrations required for such killing were several hundred-fold to several thousand-fold higher than those detected in the supernatants from infected-mice macrophages cultured with or without schistosomula. An in vitro lysozyme inhibitor, N, N, N-triacetyl chitobiose, did not abroga

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48

Bosques, Carlos J., Vincent W. F. Tai та Barbara Imperiali. "Stereoselective synthesis of β-linked TBDMS-protected chitobiose-asparagine: a versatile building block for amyloidogenic glycopeptides". Tetrahedron Letters 42, № 41 (2001): 7207–10. http://dx.doi.org/10.1016/s0040-4039(01)01524-6.

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49

Peyfoon, Elham, Benjamin Meyer, Paul G. Hitchen, et al. "The S-Layer Glycoprotein of the CrenarchaeoteSulfolobus acidocaldariusIs Glycosylated at Multiple Sites with Chitobiose-LinkedN-Glycans." Archaea 2010 (2010): 1–10. http://dx.doi.org/10.1155/2010/754101.

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Glycosylation of the S-layer of the crenarchaeaSulfolobus acidocaldariushas been investigated using glycoproteomic methodologies. The mature protein is predicted to contain 31 N-glycosylation consensus sites with approximately one third being found in the C-terminal domain spanning residuesL1004-Q1395. Since this domain is rich in Lys and Arg and therefore relatively tractable to glycoproteomic analysis, this study has focused on mapping its N-glycosylation. Our analysis identified nine of the 11 consensus sequence sites, and all were found to be glycosylated. This constitutes a remarkably hig

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50

Kiso, Makoto, Hideki Katagiri, Hiroyasu Furui, and Akira Hasegawa. "Studies on 1-Deoxynojirimycin-Containing Glycans: Synthesis of Novel Disaccharides Related to Lactose, Lactosamine, and Chitobiose." Journal of Carbohydrate Chemistry 11, no. 5 (1992): 627–44. http://dx.doi.org/10.1080/07328309208016153.

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