Synthesis of 4,5-disubstituted-3-deoxy-D-manno-octulosonic acid (Kdo) derivatives

被引：16
|
作者：
Yi, Ruiqin [1 ]
Ogaki, Atsushi [2 ]
Fukunaga, Mayumi [2 ]
Nakajima, Hiromitsu [2 ]
Ichiyanagi, Tsuyoshi [2 ]
机构：
[1] Tottori Univ, United Grad Sch Agr Sci, Tottori 6808553, Japan
[2] Tottori Univ, Fac Agr, Dept Life & Food Sci, Tottori 6808553, Japan
来源：
TETRAHEDRON | 2014年 / 70卷 / 23期
关键词：
3-Deoxy-D-manno-2-octulosonic acid; Lipopolysaccharide; Lipooligosaccharide; 4,5-Branched structure; Inner-core oligosaccharide; LIPOPOLYSACCHARIDE; GLYCOSPHINGOLIPIDS; OLIGOSACCHARIDES;
D O I：
10.1016/j.tet.2014.04.024
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this study, a new synthetic approach to 4,5-branched Kdo trisaccharides based on the common acceptor Kdo(alpha 2-4)Kdo was developed. The synthesis of three types of 4,5-branched trisaccharides, Hep(alpha 1-5)[Kdo(alpha 2-4)]Kdo, Man(alpha 1-5)[Kdo(alpha 2-4)]Kdo, and GaINAc(alpha 1-5)[Kdo(alpha 2-4)]Kdo, was achieved in good yield and high a-selectivity. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3675 / 3682
页数：8
相关论文
共 50 条
  • [21] Preparation of the phosphonic acid analogue of 3-deoxy-D-manno-2-octulosonic acid (KDO)
    Coutrot, P
    Grison, C
    Lecouvey, M
    TETRAHEDRON LETTERS, 1996, 37 (10) : 1595 - 1598
  • [22] SYNTHESIS OF 3-DEOXY-6-THIO-D-MANNO-2-OCTULOSONIC ACID (6-THIO-KDO)
    CLASSON, B
    GAREGG, PJ
    LIU, ZC
    SAMUELSSON, B
    CARBOHYDRATE RESEARCH, 1988, 174 : 369 - 374
  • [23] SYNTHESIS OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO) AND ITS ANALOGS BASED ON KDO ALDOLASE-CATALYZED REACTIONS
    SUGAI, T
    SHEN, GJ
    ICHIKAWA, Y
    WONG, CH
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (02) : 413 - 421
  • [24] Synthesis of a 3-deoxy-D-manno-octulosonic acid (KDO) building block from D-glucose via fermentation
    Camci-Unal, Gulden
    Mizanur, Rahman M.
    Chai, Yonghai
    Pohl, Nicola L. B.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (30) : 5856 - 5860
  • [25] A NEW SYNTHESIS OF 3-DEOXY-D-MANNO-OCTULOSONIC ACID ENOLLACTONES THROUGH THIOKETALE DERIVATIVES
    KORNILOV, VI
    ZHDANOV, YA
    MIKSHIEV, YM
    PAYDAK, BB
    MAKAROVA, OM
    BIOORGANICHESKAYA KHIMIYA, 1987, 13 (05): : 708 - 709
  • [26] SYNTHESIS OF 3-DEOXY-D-MANNO-OCTULOSONIC ACID BASED ON THIOACETALS
    MIKSHIEV, YM
    PAIDAK, BB
    KORNILOV, VI
    ZHDANOV, YA
    BIOORGANICHESKAYA KHIMIYA, 1990, 16 (08): : 1118 - 1124
  • [27] PREPARATION OF NOVEL PYRANOSYL FLUORIDES OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO) FEASIBLE FOR SYNTHESIS OF KDO ALPHA-GLYCOSIDES
    IMOTO, M
    KUSUNOSE, N
    MATSUURA, Y
    KUSUMOTO, S
    SHIBA, T
    TETRAHEDRON LETTERS, 1987, 28 (50) : 6277 - 6280
  • [28] A NEW SYNTHESIS OF 3-DEOXY-D-MANNO-OCTULOSONIC ACID (KDO) FROM D-MANNOSE VIA CONDENSATION OF DIOXENE
    HORITO, S
    AMANO, M
    HASHIMOTO, H
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1989, 8 (04) : 681 - 684
  • [29] Production of 3-deoxy-d-manno-octulosonic acid (KDO) by fermentation for plant lectin binding studies
    Camci-Unal, Gulden
    Pohl, Nicola L.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 237 : 697 - 697
  • [30] A novel 3-deoxy-D-manno-octulosonic acid (Kdo) hydrolase that removes the outer Kdo sugar of Helicobacter pylori lipopolysaccharide
    Stead, C
    Tran, A
    Ferguson, D
    McGrath, S
    Cotter, R
    Trent, S
    JOURNAL OF BACTERIOLOGY, 2005, 187 (10) : 3374 - 3383
12345