A Concise Synthesis of the Repeating Unit of Capsular Polysaccharide <i>Staphylococcus aureus</i> Type 8

Visansirikul, Satsawat; Yasomanee, Jagodige P.; Pornsuriyasak, Papapida; Kamat, Medha N.; Podvalnyy, Nikita M.; Gobble, Chase; Thompson, Melissa R; Kolodziej, Stephen A.; Demchenko, Alexei V.

doi:10.1021/acs.orglett.5b00899

Cited by 26 publications

(25 citation statements)

References 18 publications

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“…Along similar lines, we have also investigated the introduction of trifluoromethane-sulfonyl ester, a possible intermediate for the synthesis of mannosamine and its derivatives. Mannosamine is a common component of bacterial glycans 49–51 and a biosynthetic precursor of sialic acids. 52–54 Reactions of bromide 3 with CAN, bromide 3 with AgNO 3 , and nitrate 13 followed by sulfonylation with triflic anhydride in the presence of pyridine afforded 2- O -trifluoromethanesulfonyl tetraacetate 17 in 54%, 52% and 67% over-all yield, respectively (entries 7–9).…”

Section: Resultsmentioning

confidence: 99%

Glycosyl nitrates in synthesis: streamlined access to glucopyranose building blocks differentiated at C-2

et al. 2018

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In an attempt to refine a CAN-mediated synthesis of 1,3,4,6-tetra-O-acetyl-α-D-glucopyranose (2-OH glucose) we unexpectedly discovered that this reaction proceeds via the intermediacy of glycosyl nitrates. Improved mechanistic understanding of this reaction led to the development of a more versatile synthesis of 2-OH glucose from a variety of precursors. Also demonstrated is the conversion of 2-OH glucose into a variety of building blocks differentially protected at C-2, a position that is generally hard to protect regioselectively in the glucopyranose series.

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Section: Resultsmentioning

confidence: 99%

Glycosyl nitrates in synthesis: streamlined access to glucopyranose building blocks differentiated at C-2

et al. 2018

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“…Demchenko and co-workers reported the first total synthesis of Staphylococcus aureus type 8 capsular polysaccharide in 2015 [ 97 ]. It is a Gram positive, cluster forming, bacteria and one of the highest among all bacterial pathogens [ 98 ].…”

Section: Staphylococcus Aureus Type 8 Capsular Polysaccharidmentioning

confidence: 99%

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

Behera

Kulkarni

2018

Molecules

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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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“…aureus CP5 and CP8 have been found as highly potent antigenic targets. To date, chemical synthesis of the trisaccharide repeating units of CP5 (Danieli et al, 2012;Yasomanee et al, 2016;Hagen et al, 2017;Behera et al, 2020) and CP8 (Visansirikul et al, 2015) has been achieved. The immunological mechanism remains unclear.…”

Section: Introductionmentioning

confidence: 99%

Conjugation of Synthetic Trisaccharide of Staphylococcus aureus Type 8 Capsular Polysaccharide Elicits Antibodies Recognizing Intact Bacterium

Zhao

Qin

et al. 2020

Front. Chem.

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Staphylococcus aureus causes a wide range of life-threatening diseases. One of the powerful approaches for prevention and treatment is to develop an efficient vaccine as antibiotic resistance greatly increases. S. aureus type 8 capsular polysaccharide (CP8) has shown great potential in vaccine development. An understanding of the immunogenicity of CP8 trisaccharide repeating unit is valuable for epitope-focused vaccine design and cost-efficient vaccine production. We report the chemical synthesis of conjugation-ready CP8 trisaccharide 1 bearing an amine linker, which effectively served for immunological evaluation. The trisaccharide 1-CRM197 conjugate elicited a robust immunoglobulin G (IgG) immune response in mice. Both serum antibodies and prepared monoclonal antibodies recognized S. aureus strain, demonstrating that synthetic trisaccharide 1 can be an efficient antigen for vaccine development.

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A Concise Synthesis of the Repeating Unit of Capsular Polysaccharide Staphylococcus aureus Type 8

Cited by 26 publications

References 18 publications

Glycosyl nitrates in synthesis: streamlined access to glucopyranose building blocks differentiated at C-2

Glycosyl nitrates in synthesis: streamlined access to glucopyranose building blocks differentiated at C-2

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

Conjugation of Synthetic Trisaccharide of Staphylococcus aureus Type 8 Capsular Polysaccharide Elicits Antibodies Recognizing Intact Bacterium

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