Total Synthesis of Lipoteichoic Acid of <i>Streptococcus pneumoniae</i>

Pedersen, Christian; Figueroa-Perez, Ignacio; Lindner, Buko; Ulmer, Artur J.; Zähringer, Ulrich; Schmidt, Richard R.

doi:10.1002/anie.200906163

Cited by 57 publications

(42 citation statements)

References 49 publications

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“…45 This synthesis is summarized in Scheme 6 and is based on the block coupling of ribitol tetrasaccharide 54 and trisaccharide lipid anchor 55. 45 This synthesis is summarized in Scheme 6 and is based on the block coupling of ribitol tetrasaccharide 54 and trisaccharide lipid anchor 55.…”

Section: Chemical Synthesis Of Tasmentioning

confidence: 99%

Teichoic acids: synthesis and applications

Hogendorf

Overkleeft

et al. 2017

Chem. Soc. Rev.

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This review describes the developments in the synthesis of teichoic acids (TA) - glycosylated poly(alditolphosphates) - and the application of these fragments in immunological studies. These structurally diverse biopolymers are omnipresent constituents of the Gram-positive bacterial cell wall where they fulfill a variety of vital functions. They have been and continue to be attractive synthetic targets because of their challenging structures and the fact that their microheterogeneity precludes their isolation in single and pure enough form from natural sources. Progress in glycosylation chemistry and the development of effective phosphorylation chemistry has driven TA synthesis over the years, and highly complex and large TA structures can now reliably be targeted. Starting from the first TA synthesis in 1981, this review highlights the progress made in the field over the years. The synthesized TA fragments have been used to unravel their role in immunology and it is described how focused libraries of TAs have been used to discover the active principles of the TA polymers that interact with the innate immune system. Recently, synthetic TA fragments have also found applications as well-defined synthetic antigens for the generation of novel vaccine modalities to combat Gram-positive bacterial infections. It is foreseen that synthetic TA fragments will be valuable tools in the future to unravel the mode of action of these biomolecules at the molecular level. They will be instrumental in discovering and characterizing their designated biological binding partners, be it pattern recognition receptors or carbohydrate binding lectins or biomachinery enzymes. This review thus serves to showcase the potential of organic synthesis for (chemical) biology and immunology.

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Section: Chemical Synthesis Of Tasmentioning

confidence: 99%

Teichoic acids: synthesis and applications

Hogendorf

Overkleeft

et al. 2017

Chem. Soc. Rev.

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“…and Sauvageau et al 15. Total synthesis of a derivative of the more complex LTA from S. pneumoniae has also been achieved16 and its interaction with the host immune system revealed that not TLR‐2 but the complement pathway was activated 17. Since the structural motive is very different between the families of LTAs, and dependent on the origin, a different biological pathway is not a surprise, but what about other LTAs from other Gram‐positive bacteria?…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of Five Lipoteichoic acids of Clostridium difficile

Hogendorf

Gisch

Schwudke

et al. 2014

Chemistry A European J

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The emergence of hypervirulent resistant strains have made Clostridium difficile a notorious nosocomial pathogen and has resulted in a renewed interest in preventive strategies, such as vaccines based on (synthetic) cell wall antigens. Recently, the structure of the lipoteichoic acid (LTA) of this species has been elucidated. Additionally, this LTA was found to induce the formation of protective antibodies against C. difficile in rabbits and mice. The LTA from C. difficile is isolated as a microheterogenous mixture, differing in size and composition, impeding any structure-activity relationship studies. To ensure reliable biological results, pure and well-defined synthetic samples are required. In this work the total synthesis of LTAs from C. difficile with defined chain length is described and the initial biological results are presented.

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“…The synthesis was followed by derivatives to find the smallest structure giving activity [15][16][17] and the synthesis of LTA from other bacteria, where S. pneumoniae is a milestone. In this account the synthesis of LTA from S. aureus, 14 S. pneumoniae 18 and Streptococcus sp. DSM 8747 19 ( Figure 2) will be discussed together with their biological activities.…”

Section: Introductionmentioning

confidence: 99%

Total synthesis of biologically active lipoteichoic acids

Pedersen¹,

Bols²,

Yan³

2012

Arkivoc

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Lipoteichoic acids (LTAs) are found in the Gram positive bacteria cell wall and consist of a lipid anchor connected to a repeating unit linked together with phosphate esters. Due to the resemblance with the immune active lipopolysaccharides (LPSs) found in Gram negative bacteria, there has been interest in studying their biological role. Isolation from bacteria is complicated, and has led to inconsistent conclusions. The best way to avoid biologically active impurities in the LTA is therefore chemical synthesis, but it was not until the total synthesis of Staphylococcus aureus LTA that a clear biological activity of synthetic material could be observed. This successful synthesis was followed up by the synthesis of derivatives as well as the preparation of two other LTAs, from Streptococcus pneumoniae and Streptococcus species DSM 8747, respectively.

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Total Synthesis of Lipoteichoic Acid of Streptococcus pneumoniae

Cited by 57 publications

References 49 publications

Teichoic acids: synthesis and applications

Teichoic acids: synthesis and applications

Total Synthesis of Five Lipoteichoic acids of Clostridium difficile

Total synthesis of biologically active lipoteichoic acids

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