Synthesis of the tetrasaccharide repeating unit of the O-glycan from the polar flagellum flagellin of Azospirillum brasilense Sp7

被引:7
作者
Pal, Kumar Bhaskar [1 ]
Mukhopadhyay, Balaram [1 ]
机构
[1] Indian Inst Sci Educ & Res, Kolkata 741246, Mohanpur, India
关键词
Flagellin O-glycan; Total synthesis; H2SO4-silica; PSEUDOMONAS-AERUGINOSA; CONCISE SYNTHESIS; GLYCOSYLATION; MOTILITY; LIPOPOLYSACCHARIDE; POLYSACCHARIDE; THIOGLYCOSIDES; IDENTIFICATION;
D O I
10.1016/j.carres.2014.06.019
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Chemical synthesis of the tetrasaccharide repeating unit of the O-glycan from the polar flagellum flagellin of Azospirillum brasilense Sp7 in the form of its p-methoxyphenyl glycoside is reported. The required glycosidic linkages have been accomplished by activation of thioglycosides with N-iodosuccinimide in the presence of H2SO4-silica. H2SO4-silica was found to be an effective alternative to the classical acid promoters like TfOH or TMSOTf and it can lead to the formation of both 1,2-cis and 1,2-trans glycosidic linkages depending on the protecting group manipulation and control of the reaction condition. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9 / 13
页数:5
相关论文
共 23 条
  • [1] Abbau der Reduzierenden Biosen, 1926, BIOCHEM, V59, P1254, DOI [10.1002/cber.19260590626, DOI 10.1002/CBER.19260590626]
  • [2] Identification of an O-linked repetitive glycan chain of the polar flagellum flagellin of Azospirillum brasilense Sp7
    Belyakov, Alexei Ye.
    Burygin, Gennady L.
    Arbatsky, Nikolai P.
    Shashkov, Alexander S.
    Selivanov, Nikolai Yu.
    Matora, Larisa Yu.
    Knirel, Yuriy A.
    Shchyogolev, Sergei Yu.
    [J]. CARBOHYDRATE RESEARCH, 2012, 361 : 127 - 132
  • [3] Why are the hydroxy groups of partially protected N-acetylglucosamine derivatives such poor glycosyl accepters, and what can be done about it?: A comparative study of the reactivity of N-acetyl-, N-phthalimido-, and 2-azido-2-deoxy-glucosamine derivatives in glycosylation.: 2-picolinyl ethers as reactivity-enhancing replacements for benzyl ethers
    Crich, D
    Dudkin, V
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) : 6819 - 6825
  • [4] IDENTIFICATION AND MAPPING OF LOCI INVOLVED IN MOTILITY, ADSORPTION TO WHEAT ROOTS, COLONY MORPHOLOGY, AND GROWTH IN MINIMAL MEDIUM ON THE AZOSPIRILLUM-BRASILENSE SP7 90-MDA PLASMID
    CROES, C
    VANBASTELAERE, E
    DECLERCQ, E
    EYERS, M
    VANDERLEYDEN, J
    MICHIELS, K
    [J]. PLASMID, 1991, 26 (02) : 83 - 93
  • [5] NIS/H2SO4-silica:: a mild and efficient reagent system for the hydrolysis of thioglycosides
    Dasgupta, Somnath
    Roy, Birnalendu
    Mukhopadhyay, Balaram
    [J]. CARBOHYDRATE RESEARCH, 2006, 341 (16) : 2708 - 2713
  • [6] Regioselective reduction of 4,6-O-benzylidenes using triethylsilane and BF3•Et2O
    Debenham, SD
    Toone, EJ
    [J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (02) : 385 - 387
  • [7] Gent P. A., 1974, J CHEM SOC P1, V1, P1446
  • [8] Structural establishment of polygalatenosides A and B by total synthesis
    Huang, Chih-Ming
    Liu, Rai-Shung
    Wu, Tian-Shung
    Cheng, Wei-Chieh
    [J]. TETRAHEDRON LETTERS, 2008, 49 (18) : 2895 - 2898
  • [9] ACCEPTOR SUBSTRATE RECOGNITION BY N-ACETYLGLUCOSAMINYLTRANSFERASE-V - CRITICAL ROLE OF THE 4''-HYDROXYL GROUP IN BETA-D-GLCPNAC-(1-)2)-ALPHA-D-MANP(1-)6)-BETA-D-GLCP-OR
    KANIE, O
    CRAWLEY, SC
    PALCIC, MM
    HINDSGAUL, O
    [J]. CARBOHYDRATE RESEARCH, 1993, 243 (01) : 139 - 164
  • [10] Truncation in the core oligosaccharide of lipopolysaccharide affects flagella-mediated motility in Pseudomonas aeruginosa PAO1 via modulation of cell surface attachment
    Lindhout, Theresa
    Lau, Peter C. Y.
    Brewer, Dyanne
    Lam, Joseph S.
    [J]. MICROBIOLOGY-SGM, 2009, 155 : 3449 - 3460