Synthesis of the sialylated pentasaccharide repeating unit of the capsular polysaccharide of Streptococcus group B type VI

被引：2
|
作者：
Manna, Tapasi [1 ]
Misra, Anup Kumar [1 ]
机构：
[1] Bose Inst, Div Mol Med, P-1-12,CIT Scheme 7-M, Kolkata 700054, India
来源：
CARBOHYDRATE RESEARCH | 2021年 / 502卷
关键词：
Oligosaccharide; Glycosylation; O-antigen; Capsular polysaccharide; Sialic acid; Streptococcus; SIALIC-ACID DONORS; PROMOTED REACTIONS; CHEMICAL-SYNTHESIS; EFFICIENT; GLYCOSYLATION; VIRULENCE; OLIGOSACCHARIDES; THIOGLYCOSIDE; ACETYLATION; CONVERSION;
D O I：
10.1016/j.carres.2021.108294
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：
An efficient synthetic strategy has been developed for the synthesis of the sialic acid containing pentasaccharide repeating unit of the cell wall O-antigen of Streptococcus group B type VI strain involving stereoselective alpha-glycosylation of sialic acid thioglycoside derivative. Stereoselective glycosylation of glycosyl trichloroacetimidate derivatives and thioglycosides were carried out using perchloric acid supported over silica (HClO4-SiO2) as a solid acid catalyst. A panel of sialic acid donors has been screened for achieving satisfactory yield and stereochemical outcome of the glycosylation reaction.
引用
收藏
页数：7
相关论文
共 50 条
  • [1] Chemical Synthesis of the Repeating Unit of Type la Group B Streptococcus Capsular Polysaccharide
    Mondal, Prolay K.
    Liao, Guochao
    Mondal, Mohabul A.
    Guo, Zhongwu
    ORGANIC LETTERS, 2015, 17 (05) : 1102 - 1105
  • [2] Chemical Synthesis of the Repeating Unit of Type II Group B Streptococcus Capsular Polysaccharide
    Shao, Liming
    Zhang, Han
    Li, Yaoyao
    Gu, Guofeng
    Cai, Feng
    Guo, Zhongwu
    Gao, Jian
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (11): : 5920 - 5930
  • [3] Chemical Synthesis of the Repeating Unit of Type V Group B Streptococcus Capsular Polysaccharide
    Gao, Jian
    Guo, Zhongwu
    ORGANIC LETTERS, 2016, 18 (21) : 5552 - 5555
  • [4] Chemical synthesis of the dimeric repeating unit of type Ia group B Streptococcus capsular polysaccharide
    Zhang, Han
    Zhou, Shihao
    Zhao, Ying
    Gao, Jian
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (23) : 5839 - 5848
  • [5] CORRECT STRUCTURE OF REPEATING UNIT OF GROUP-B STREPTOCOCCUS TYPE-III CAPSULAR POLYSACCHARIDE
    WESSELS, MR
    KASPER, DL
    JOURNAL OF INFECTIOUS DISEASES, 1990, 162 (06): : 1412 - 1412
  • [6] SYNTHESIS OF A REPEATING PENTASACCHARIDE FRAGMENT OF THE CAPSULAR POLYSACCHARIDE OF STREPTOCOCCUS-PNEUMONIAE TYPE-18C
    VANSTEIJN, AMP
    VANDERVEN, JGM
    VANSEEVENTER, P
    KAMERLING, JP
    VLIEGENTHART, JFG
    CARBOHYDRATE RESEARCH, 1992, 229 (01) : 155 - 160
  • [7] Synthesis of a pseudotetrasaccharide corresponding to a repeating unit of the Streptococcus pneumoniae type 6B capsular polysaccharide*
    Sukhova, Elena V.
    Yashunsky, Dmitry V.
    Kurbatova, Ekaterina A.
    Tsvetkov, Yury E.
    Nifantiev, Nikolay E.
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 2018, 37 (01) : 1 - 17
  • [8] Synthesis of a single repeat unit of type VIII Group B Streptococcus capsular polysaccharide
    Eichler, E
    Jennings, HJ
    Whitfield, DM
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1997, 16 (4-5) : 385 - 411
  • [9] Synthesis of a Single Repeat Unit of Type VIII Group B Streptococcus Capsular Polysaccharide
    Journal of Carbohydrate Chemistry, 16 (4-5):
  • [10] Capsular polysaccharide of Streptococcus pneumoniae type 19F:: synthesis of the repeating unit
    Bousquet, E
    Khitri, M
    Lay, L
    Nicotra, F
    Panza, L
    Russo, G
    CARBOHYDRATE RESEARCH, 1998, 311 (04) : 171 - 181
12345