Issue 5, 2017

Teichoic acids: synthesis and applications


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.

Graphical abstract: Teichoic acids: synthesis and applications

Article information

Article type
Review Article
31 Mar 2016
First published
19 Dec 2016
This article is Open Access
Creative Commons BY license

Chem. Soc. Rev., 2017,46, 1464-1482

Teichoic acids: synthesis and applications

D. van der Es, W. F. J. Hogendorf, H. S. Overkleeft, G. A. van der Marel and J. D. C. Codée, Chem. Soc. Rev., 2017, 46, 1464 DOI: 10.1039/C6CS00270F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity