Total synthesis of five lipoteichoic acids of Clostridium difficile

Wouter Frederik Johan Hogendorf; Nicolas Gisch; Dominik Schwudke; Holger Heine; Mikael Bols; Christian Marcus Pedersen

doi:10.1002/chem.201404336

Total synthesis of five lipoteichoic acids of Clostridium difficile

Wouter Frederik Johan Hogendorf, Nicolas Gisch, Dominik Schwudke, Holger Heine, Mikael Bols, Christian Marcus Pedersen

Department of Chemistry

7 Citations (Scopus)

Abstract

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.

Original language	English
Journal	Chemistry: A European Journal
Volume	20
Issue number	42
Pages (from-to)	13511-13516
Number of pages	6
ISSN	0947-6539
DOIs	https://doi.org/10.1002/chem.201404336
Publication status	Published - 13 Oct 2014

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title = "Total synthesis of five lipoteichoic acids of Clostridium difficile",

abstract = "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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T1 - Total synthesis of five lipoteichoic acids of Clostridium difficile

AU - Hogendorf, Wouter Frederik Johan

AU - Gisch, Nicolas

AU - Schwudke, Dominik

AU - Heine, Holger

AU - Bols, Mikael

AU - Pedersen, Christian Marcus

PY - 2014/10/13

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N2 - 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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Total synthesis of five lipoteichoic acids of Clostridium difficile

Abstract

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