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

Behera, Archanamayee; Kulkarni, Suvarn S.

doi:10.3390/molecules23081997

Cited by 25 publications

(12 citation statements)

References 132 publications

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“…Such constructs would be pivotal for the development of glycoconjugate vaccines. [ 30 ] The rare monosaccharides can be employed in metabolic oligosaccharide engineering to develop novel diagnostics and therapeutics. [ 31 ] From the above discussion, it is clear that the synthesis of bacterial nonulosonic acids presents a next‐level challenge and although several remarkable synthetic approaches have been established over the years, there is still scope for further improvement.…”

Section: Discussionmentioning

confidence: 99%

Synthesis of Nonulosonic Acids

Pradhan

Kulkarni

2020

Eur J Org Chem

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Bacterial cell‐surface nonulosonic acids are unique in their structural complexity and their biological roles in life processes. Their presence at the non‐reducing end of bacterial cell surface glycans makes them key players in infections related to various multidrug‐resistant pathogens. These glycans are difficult to isolate from natural sources in pure form. Also, due to their complicated structures, access to these rare sugars through synthesis is highly challenging. The most well‐studied bacterial nonulosonic acid is pseudaminic acid which has been synthesized by many groups and reviewed very recently. In this minireview, we discuss the recent advances in the synthesis of remaining nonulosonic acids viz. legionaminic acid, acinetaminic acid, and fusaminic acid.

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Section: Discussionmentioning

confidence: 99%

Synthesis of Nonulosonic Acids

Pradhan

Kulkarni

2020

Eur J Org Chem

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“…Classical vaccines were obtained via isolation of polysaccharides directly from pathogens, but site-selective conjugations, protein modifications using unnatural amino acids and chemical or enzymatic modifications of native amino acids, and the bioengineering of carbohydrates (glycoengineering) are beginning to redefine this field [108]. Chemists can now also synthesize rare deoxy sugars found in bacterial cell surfaces, but not in humans, which may facilitate the development of new glycoconjugate vaccines [109].…”

Section: Novel Antimicrobial Moleculesmentioning

confidence: 99%

The Quest for Novel Antimicrobial Compounds: Emerging Trends in Research, Development, and Technologies

et al. 2019

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Pathogenic antibiotic resistant bacteria pose one of the most important health challenges of the 21st century. The overuse and abuse of antibiotics coupled with the natural evolutionary processes of bacteria has led to this crisis. Only incremental advances in antibiotic development have occurred over the last 30 years. Novel classes of molecules, such as engineered antibodies, antibiotic enhancers, siderophore conjugates, engineered phages, photo-switchable antibiotics, and genome editing facilitated by the CRISPR/Cas system, are providing new avenues to facilitate the development of antimicrobial therapies. The informatics revolution is transforming research and development efforts to discover novel antibiotics. The explosion of nanotechnology and micro-engineering is driving the invention of antimicrobial materials, enabling the cultivation of “uncultivable” microbes and creating specific and rapid diagnostic technologies. Finally, a revival in the ecological aspects of microbial disease management, the growth of prebiotics, and integrated management based on the “One Health” model, provide additional avenues to manage this health crisis. These, and future scientific and technological developments, must be coupled and aligned with sound policy and public awareness to address the risks posed by rising antibiotic resistance.

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“…The LPS and LOS oligosaccharides and analogs obtained (Figure 2B) include those from B. pertussis (26) [60] ** ; P. aeruginosa STO11 (27) [61] ** ; P. shigelloide ST51 (28) [62]; B. cenocepacia (29) [28]; P. fluorescens BIM B-582 (30) [63]; H. pylori STO2 (31) [29] ** ; K. pneumoniae O2a (32) [30] ** ; P. chloroaphis UCM B-106 (33) [64]; S. boydii type type 18 (34) [65]; S. enteritidis (35) [31]; S. paratyphi A (36) [32] ** ; S. enterica O41 (37) [33], O51 (38) [66], O60 (39) [67]; E. coli O43 (40) [68], O75 (41) [69], O115 (42) [34], O156 (43) [70]; A. doebereinerae type strain GSF71 T (44) [71], P. alcalifaciens O22 (45) [78], rhizobial and agrobacterial LPS inner core (46) [72]; and C. jejuni LOS core (47) [35] ** ; Bradyrhizobium sp. BTAi1 (48) [36] ** and P. cryohalolentis K5 T (49) [37].…”

Section: Chemically Synthesized Bacterial Surface Oligosaccharidesmentioning

confidence: 99%

Recent progress in chemical synthesis of bacterial surface glycans

Chen

2020

Current Opinion in Chemical Biology

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With the continuing advancement of carbohydrate chemical synthesis, bacterial glycomes have become increasingly attractive and accessible synthetic targets. While bacteria also produce carbohydrate-containing secondary metabolites, our review here will cover recent chemical synthetic efforts on bacterial surface glycans. The obtained compounds are excellent candidates for the development of improved structurally defined glycoconjugate vaccines against bacterial infection. They are also important probes for investigating glycan-protein interactions. Glycosylation strategies applied for the formation of some challenging glycosidic bonds of various uncommon sugars in a number of recently synthesized bacterial surface glycans are highlighted.

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

Cited by 25 publications

References 132 publications

Synthesis of Nonulosonic Acids

Synthesis of Nonulosonic Acids

The Quest for Novel Antimicrobial Compounds: Emerging Trends in Research, Development, and Technologies

Recent progress in chemical synthesis of bacterial surface glycans

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