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
[1]   Comparative bioinformatics analysis of the mammalian and bacterial glycomes [J].
Adibekian, Alexander ;
Stallforth, Pierre ;
Hecht, Marie-Lyn ;
Werz, Daniel B. ;
Gagneux, Pascal ;
Seeberger, Peter H. .
CHEMICAL SCIENCE, 2011, 2 (02) :337-344
[2]  
Ala'Aldeen D.A.A., 2004, Staphylococcus aureus: Molecular and Clinical Aspects
[3]   Synthesis of N-linked glycan derived from Gram-negative bacterium, Campylobacter jejuni [J].
Amin, Mohammed Nurul ;
Ishiwata, Akihiro ;
Ito, Yukishige .
TETRAHEDRON, 2007, 63 (34) :8181-8198
[4]   Synthesis of asparagine-linked bacillosamine [J].
Amin, Mohammed Nurul ;
Ishiwata, Akihiro ;
Ito, Yukishige .
CARBOHYDRATE RESEARCH, 2006, 341 (11) :1922-1929
[5]  
[Anonymous], FACT SHEETS MEN MEN
[6]   A mechanism for glycoconjugate vaccine activation of the adaptive immune system and its implications for vaccine design [J].
Avci, Fikri Y. ;
Li, Xiangming ;
Tsuji, Moriya ;
Kasper, Dennis L. .
NATURE MEDICINE, 2011, 17 (12) :1602-U115
[7]   How Bacterial Carbohydrates Influence the Adaptive Immune System [J].
Avci, Fikri Y. ;
Kasper, Dennis L. .
ANNUAL REVIEW OF IMMUNOLOGY, VOL 28, 2010, 28 :107-130
[8]   Progress and pitfalls in Shigella vaccine research [J].
Barry, Eileen M. ;
Pasetti, Marcela F. ;
Sztein, Marcelo B. ;
Fasano, Alessio ;
Kotloff, Karen L. ;
Levine, Myron M. .
NATURE REVIEWS GASTROENTEROLOGY & HEPATOLOGY, 2013, 10 (04) :245-255
[9]   STRUCTURAL ELUCIDATION OF 2 CAPSULAR POLYSACCHARIDES FROM ONE STRAIN OF BACTEROIDES-FRAGILIS USING HIGH-RESOLUTION NMR-SPECTROSCOPY [J].
BAUMANN, H ;
TZIANABOS, AO ;
BRISSON, JR ;
KASPER, DL ;
JENNINGS, HJ .
BIOCHEMISTRY, 1992, 31 (16) :4081-4089
[10]   The structure of the O-specific polysaccharide of the lipopolysaccharide from Yersinia enterocolitica serotype O:50 strain 3229 [J].
Beczala, Agnieszka ;
Duda, Katarzyna Anna ;
Skurnik, Mikael ;
Holst, Otto .
CARBOHYDRATE RESEARCH, 2012, 359 :97-101