Structure of the O-antigen of Acinetobacter lwoffii EK30A; identification of D-homoserine, a novel non-sugar component of bacterial polysaccharides

被引：9
作者：
Arbatsky, Nikolay P. [1 ]
Kondakova, Anna N. [1 ]
Shashkov, Alexander S. [1 ]
Drutskaya, Marina S. [2 ]
Belousov, Pavel V. [2 ,3 ]
Nedospasov, Sergei A. [2 ,3 ]
Petrova, Mayya A. [4 ]
Knirel, Yuriy A. [1 ]
机构：
[1] Russian Acad Sci, Zelinsky Inst Organ Chem, Moscow 119991, Russia
[2] Russian Acad Sci, VA Engelhardt Mol Biol Inst, Moscow 119991, Russia
[3] Moscow MV Lomonosov State Univ, Belozersky Inst Physicochem Biol, Moscow 119991, Russia
[4] Russian Acad Sci, Inst Mol Genet, Moscow 123182, Russia
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 15期
基金：
俄罗斯基础研究基金会;
关键词：
PROTEUS; LIPOPOLYSACCHARIDE; ACID; F78;
D O I：
10.1039/c004090h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We established a peculiar structure of the O-specific polysaccharide (O-antigen) of a psychrotrophic strain of Acinetobacter lwoffii, EK30A, isolated from a 1.6-1.8 million-year-old Siberian permafrost subsoil sediment sample. The polysaccharide was released by mild acid degradation of the lipopolysaccharide and studied using chemical analyses, Smith degradation, (1)H and (13)C NMR spectroscopy and mass spectrometry. It was found to contain D-homoserine, which is N-linked to 4-amino-4,6-dideoxy-D-glucose (Qui4N) and is N-acylated itself with acetyl in about half of the repeating units or (S)-3-hydroxybutanoyl group in the other half. The following is the structure of the tetrasaccharide repeating unit of the polysaccharide: -> 3)-beta-D-Quip4NAcyl-(1 -> 6)-alpha-D-Galp-(1 -> 4)-alpha-D-GalpNAc-(1 -> 3)-alpha-D-FucpNAc-(1 -> where Acyl stands for either N-acetyl- or N-[(S)-3-hydroxybutanoyl]-D-homoseryl.
引用
收藏
页码：3571 / 3577
页数：7
相关论文
共 24 条
  • [1] C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF MONOSACCHARIDES
    BOCK, K
    PEDERSEN, C
    [J]. ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1983, 41 : 27 - 66
  • [2] The molecular basis of the host response to lipopolysaccharide
    Bryant, Clare E.
    Spring, David R.
    Gangloff, Monique
    Gay, Nicholas J.
    [J]. NATURE REVIEWS MICROBIOLOGY, 2010, 8 (01) : 8 - 14
  • [3] The allergy-protective properties of Acinetobacter lwoffii F78 are imparted by its lipopolysaccharide
    Debarry, J.
    Hanuszkiewicz, A.
    Stein, K.
    Holst, O.
    Heine, H.
    [J]. ALLERGY, 2010, 65 (06) : 690 - 697
  • [4] Gerischer U., 2008, ACINETOBACTER MOL BI
  • [5] Structure of an acidic O-specific polysaccharide of Pseudoalteromonas haloplanktis type strain ATCC 14393 containing 2-acetamido-2-deoxy-D- and -L-galacturonic acids and 3-(N-acetyl-D-alanyl)amino-3,6-dideoxy-D-glucose
    Hanniffy, OM
    Shashkov, AS
    Senchenkova, SN
    Tomshich, SV
    Komandrova, NA
    Romanenko, LA
    Knirel, YA
    Savage, AV
    [J]. CARBOHYDRATE RESEARCH, 1999, 321 (1-2) : 132 - 138
  • [6] Structural and Immunochemical Analysis of the Lipopolysaccharide from Acinetobacter Iwoffii F78 Located Outside Chlamydiaceae with a Chlamydia-Specific Lipopolysaccharide Epitope
    Hanuszkiewicz, Anna
    Huebner, Goeran
    Vinogradov, Evgeny
    Lindner, Buko
    Brade, Lore
    Brade, Helmut
    Debarry, Jennifer
    Heine, Holger
    Holst, Otto
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (33) : 10251 - 10258
  • [7] THE STRUCTURE OF A GLYCEROL TEICHOIC ACID-LIKE O-SPECIFIC POLYSACCHARIDE OF HAFNIA-ALVEI 1205
    KATZENELLENBOGEN, E
    ROMANOWSKA, E
    KOCHAROVA, NA
    KNIREL, YA
    SHASHKOV, AS
    KOCHETKOV, NK
    [J]. CARBOHYDRATE RESEARCH, 1992, 231 : 249 - 260
  • [8] Structure of a polysaccharide from the lipopolusaccharide of Vibrio vulnificus CECT4602 containing 2-acetamido-2,3,6-trideoxy-3-[(S)- and (R)-3-hydroxybutanoylamino]-L-mannose
    Knirel, Yuriy A.
    Senchenkova, Sofya N.
    Shashkov, Alexander S.
    Esteve, Consuelo
    Alcaide, Elena
    Merino, Susana
    Tomas, Juan M.
    [J]. CARBOHYDRATE RESEARCH, 2009, 344 (04) : 479 - 483
  • [9] N-(1-Carboxyethyl)alanine (alanopine), a new non-sugar component of lipopolysaccharides of Providencia and Proteus
    Kocharova, Nina A.
    Kondakova, Anna N.
    Ovchinnikova, Olga G.
    Perepelov, Andrei V.
    Shashkov, Alexander S.
    Knirel, Yuriy A.
    [J]. CARBOHYDRATE RESEARCH, 2009, 344 (15) : 2060 - 2062
  • [10] New structures of the O-speciftic polysaccharides of proteus.: 4.: Polysaccharides containing unusual acidic N-acyl derivatives of 4-amino-4,6-dideoxy-D-glucose
    Kondakova, AN
    Linder, B
    Fudala, R
    Senchenkova, SN
    Moll, H
    Shashkov, AS
    Kaca, W
    Zähringer, U
    Knirel, YA
    [J]. BIOCHEMISTRY-MOSCOW, 2004, 69 (09) : 1034 - 1043
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