Straightforward synthesis of a tetrasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O16

被引:3
|
作者
Jana, Manas [1 ]
Misra, Anup Kumar [1 ]
机构
[1] Bose Inst, Div Mol Med, Kolkata 700054, India
关键词
Escherichia coli; glycosylation; lipopolysaccharide; O-antigen; tetrasaccharide; BACTERIAL-MENINGITIS; PROMOTED REACTIONS; POLYSACCHARIDE; INFANTS; SEPSIS; ETHER;
D O I
10.3762/bjoc.9.203
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A straightforward synthesis of the tetrasaccharide repeating unit of the O-antigen of Escherichia coli O16 has been achieved following a sequential glycosylation strategy. A minimum number of steps was used for the synthesis of the target compound involving a one-pot glycosylation and a protecting group manipulation. All intermediate reactions afford their products in high yield, and the glycosylation steps are stereoselective.
引用
收藏
页码:1757 / 1762
页数:6
相关论文
共 50 条
  • [31] Synthesis of the tetrasaccharide repeating unit of the antigen from Escherichia coli O126 as its methyl glycoside
    Misra, AK
    Roy, N
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1998, 17 (07) : 1047 - 1056
  • [32] Expedient synthesis of the pentasaccharide repeating unit of the O-antigen of Escherichia coli O86 and its conformational analysis
    Ishani Bhaumik
    Rajiv Kumar Kar
    Anirban Bhunia
    Anup Kumar Misra
    Glycoconjugate Journal, 2016, 33 : 887 - 896
  • [33] Expedient synthesis of the pentasaccharide repeating unit of the O-antigen of Escherichia coli O86 and its conformational analysis
    Bhaumik, Ishani
    Kar, Rajiv Kumar
    Bhunia, Anirban
    Misra, Anup Kumar
    GLYCOCONJUGATE JOURNAL, 2016, 33 (06) : 887 - 896
  • [34] Synthesis of the trisaccharide repeating unit of the O-antigen related to the enterohemorrhagic Escherichia coli type 026:H
    Sarkar, K
    Mukherjee, I
    Roy, N
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 2003, 22 (02) : 95 - 107
  • [35] Mass spectrometric characterization of a two-glycosyltransferase tandem reaction for assembly of tetrasaccharide repeating unit of Escherichia coli O77 O-antigen
    Zhou, Dawei
    Chen, Chao
    Xu, Lingling
    Utkina, Natalia
    Danilov, Leonid
    Torgov, Vladimir
    Veselovsky, Vladimir
    Liu, Bin
    Feng, Lu
    CARBOHYDRATE RESEARCH, 2016, 424 : 24 - 29
  • [36] Concise Synthesis of a Pentasaccharide Repeating Unit Corresponding to the O-Antigen of Salmonella Enterica O51
    Bhaumik, Ishani
    Misra, Anup Kumar
    CHEMISTRYSELECT, 2017, 2 (03): : 937 - 939
  • [37] Total Synthesis of a Conjugation-Ready Tetrasaccharide Repeating Unit of Vibrio cholerae O:3 O-antigen Polysaccharide
    Maji, Soumyakanta
    Ghotekar, Balasaheb K.
    Kulkarni, Suvarn S.
    ORGANIC LETTERS, 2024, 26 (03) : 745 - 750
  • [38] Concise synthesis of a tetrasaccharide related to the repeating unit of the cell wall O-antigen of Salmonella enterica 060
    Gucchait, Arin
    Shit, Pradip
    Misra, Anup Kumar
    TETRAHEDRON, 2020, 76 (34)
  • [39] ARTIFICIAL CARBOHYDRATE ANTIGENS - THE SYNTHESIS OF A TETRASACCHARIDE HAPTEN, A SHIGELLA-FLEXNERI O-ANTIGEN REPEATING UNIT
    BUNDLE, DR
    JOSEPHSON, S
    CARBOHYDRATE RESEARCH, 1980, 80 (01) : 75 - 85
  • [40] Linear synthesis and conformational analysis of the pentasaccharide repeating unit of the cell wall O-antigen of Escherichia coli O13
    Santra, Abhishek
    Si, Anshupriya
    Kar, Rajiv Kumar
    Bhunia, Anirban
    Misra, Anup Kumar
    CARBOHYDRATE RESEARCH, 2014, 391 : 9 - 15