Chemical Synthesis of Rare, Deoxy-Amino Sugars Containing Bacterial Glycoconjugates as Potential Vaccine Candidates

被引:28
作者
Behera, Archanamayee [1 ]
Kulkarni, Suvarn S. [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India
关键词
bacterial glycoconjugates; rare deoxy-amino sugars; total synthesis; vaccine candidates; zwitterionic polysaccharides; stereoselective glycosylation; GRAM-NEGATIVE BACTERIUM; N-LINKED GLYCAN; AUREUS TYPE 5; O-SPECIFIC POLYSACCHARIDE; CAPSULAR POLYSACCHARIDE; REPEATING UNIT; PLESIOMONAS-SHIGELLOIDES; LIPOTEICHOIC ACID; BUILDING-BLOCKS; YERSINIA-ENTEROCOLITICA;
D O I
10.3390/molecules23081997
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
Bacteria often contain rare deoxy amino sugars which are absent in the host cells. This structural difference can be harnessed for the development of vaccines. Over the last fifteen years, remarkable progress has been made toward the development of novel and efficient protocols for obtaining the rare sugar building blocks and their stereoselective assembly to construct conjugation ready bacterial glycans. In this review, we discuss the total synthesis of a variety of rare sugar containing bacterial glycoconjugates which are potential vaccine candidates.
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页数:36
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共 132 条
[11]   Sulfoxide covalent catalysis: Application to glycosidic bond formation [J].
Boebel, TA ;
Gin, DY .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (47) :5874-5877
[12]   Bad Bugs, No Drugs: No ESKAPE! An Update from the Infectious Diseases Society of America [J].
Boucher, Helen W. ;
Talbot, George H. ;
Bradley, John S. ;
Edwards, John E., Jr. ;
Gilbert, David ;
Rice, Louis B. ;
Scheld, Michael ;
Spellberg, Brad ;
Bartlett, John .
CLINICAL INFECTIOUS DISEASES, 2009, 48 (01) :1-12
[13]   Environmental and Biofilm-dependent Changes in a Bacillus cereus Secondary Cell Wall Polysaccharide [J].
Candela, Thomas ;
Maes, Emmanuel ;
Garenaux, Estelle ;
Rombouts, Yoann ;
Krzewinski, Frederic ;
Gohar, Michel ;
Guerardel, Yann .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2011, 286 (36) :31250-31262
[14]   Structural characterization of the Pseudomonas aeruginosa 1244 pilin glycan [J].
Castric, P ;
Cassels, FJ ;
Carlson, RW .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (28) :26479-26485
[15]   A unique structural pattern shared by T-cell-activating and abscess-regulating zwitterionic polysaccharides [J].
Choi, YH ;
Roehrl, MH ;
Kasper, DL ;
Wang, JY .
BIOCHEMISTRY, 2002, 41 (51) :15144-15151
[16]   Galacturonic Acid Lactones in the Synthesis of All Trisaccharide Repeating Units of the Zwitterionic Polysaccharide Sp1 [J].
Christina, Alphert E. ;
van den Bos, Leendert J. ;
Overkleeft, Herman S. ;
van der Marel, Gijsbert A. ;
Codee, Jeroen D. C. .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (06) :1692-1706
[17]   Development of Rare Bacterial Monosaccharide Analogs for Metabolic Glycan Labeling in Pathogenic Bacteria [J].
Clark, Emily L. ;
Emmadi, Madhu ;
Krupp, Katharine L. ;
Podilapu, Ananda R. ;
Helble, Jennifer D. ;
Kulkarni, Suvarn S. ;
Dube, Danielle H. .
ACS CHEMICAL BIOLOGY, 2016, 11 (12) :3365-3373
[18]   Polysaccharide processing and presentation by the MHCII pathway [J].
Cobb, BA ;
Wang, O ;
Tzianabos, AO ;
Kasper, DL .
CELL, 2004, 117 (05) :677-687
[19]   Zwitterionic capsular polysaccharides: the new MHCII-dependent antigens [J].
Cobb, BA ;
Kasper, DL .
CELLULAR MICROBIOLOGY, 2005, 7 (10) :1398-1403
[20]   Characteristics of carbohydrate antigen binding to the presentation protein HLA-DR [J].
Cobb, Brian A. ;
Kasper, Dennis L. .
GLYCOBIOLOGY, 2008, 18 (09) :707-718