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

Overview
Journal Molecules
Publisher MDPI
Specialty Biology
Date 2018 Aug 15
PMID 30103434
Citations 9
Authors
Affiliations
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Abstract

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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References
1.
Nishat S, Andreana P . Entirely Carbohydrate-Based Vaccines: An Emerging Field for Specific and Selective Immune Responses. Vaccines (Basel). 2016; 4(2). PMC: 4931636. DOI: 10.3390/vaccines4020019. View

2.
Glover K, Weerapana E, Numao S, Imperiali B . Chemoenzymatic synthesis of glycopeptides with PglB, a bacterial oligosaccharyl transferase from Campylobacter jejuni. Chem Biol. 2005; 12(12):1311-5. PMC: 2519243. DOI: 10.1016/j.chembiol.2005.10.004. View

3.
De Silva R, Wang Q, Chidley T, Appulage D, Andreana P . Immunological response from an entirely carbohydrate antigen: design of synthetic vaccines based on Tn-PS A1 conjugates. J Am Chem Soc. 2009; 131(28):9622-3. DOI: 10.1021/ja902607a. View

4.
Drobniewski F . Bacillus cereus and related species. Clin Microbiol Rev. 1993; 6(4):324-38. PMC: 358292. DOI: 10.1128/CMR.6.4.324. View

5.
Pedersen C, Figueroa-Perez I, Boruwa J, Lindner B, Ulmer A, Zahringer U . Synthesis of the core structure of the lipoteichoic acid of Streptococcus pneumoniae. Chemistry. 2010; 16(42):12627-41. DOI: 10.1002/chem.201001204. View