Dienophile-Modified Mannosamine Derivatives for Metabolic Labeling of Sialic Acids : A Comparative Study

Dold, Jeremias E.G.A.; Pfotzer, Jessica; Späte, Anne-Katrin; Wittmann, Valentin

Dienophile-Modified Mannosamine Derivatives for Metabolic Labeling of Sialic Acids : A Comparative Study

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Date

2017

Authors

Dold, Jeremias E.G.A.

Pfotzer, Jessica

Späte, Anne-Katrin

Wittmann, Valentin

DOI (citable link)

10.1002/cbic.201700002

Collections

Chemie

Publication type

Journal article

Publication status

Published

Published in

ChemBioChem ; 18 (2017), 13. - pp. 1242-1250. - ISSN 1439-4227. - eISSN 1439-7633

Abstract

Sialic acids play an important role in numerous cell adhesion processes, and sialylation levels are known to be altered under certain pathogenic conditions, such as cancer. Metabolic glycoengineering with mannosamine derivatives is a convenient way to introduce non-natural chemical reporter groups into sialylated glycoconjugates, offering the opportunity to label sialic acids by using bioorthogonal ligation chemistry. The labeling intensity depends not only on the rate of the ligation reaction but also on the extent to which the natural sialic acids are replaced by the modified ones; that is, the incorporation efficiency. Here, we present a comparative study of eight mannosamine derivatives featuring terminal alkenes as chemical reporter groups that can be labeled by an inverse-electron-demand Diels-Alder (DAinv) reaction. The derivatives differed in chain length as well as the type of linkage (carbamates, amides, and a urea) that connects the terminal alkene to the sugar. As a general trend, increasing chain lengths resulted in higher DAinv reactivity and, at the same time, reduced incorporation efficiency. Carbamates were better accepted than amides with the same chain length; nevertheless, the latter resulted in more intense cell-surface staining, visible by live-cell fluorescence microscopy. A urea derivative was also shown to be accepted.

Subject (DDC)

540 Chemistry

Cite This

ISO 690

DOLD, Jeremias E.G.A., Jessica PFOTZER, Anne-Katrin SPÄTE, Valentin WITTMANN, 2017. Dienophile-Modified Mannosamine Derivatives for Metabolic Labeling of Sialic Acids : A Comparative Study. In: ChemBioChem. 18(13), pp. 1242-1250. ISSN 1439-4227. eISSN 1439-7633. Available under: doi: 10.1002/cbic.201700002

BibTex

@article{Dold2017-07-04Dieno-40021,
  year={2017},
  doi={10.1002/cbic.201700002},
  title={Dienophile-Modified Mannosamine Derivatives for Metabolic Labeling of Sialic Acids : A Comparative Study},
  number={13},
  volume={18},
  issn={1439-4227},
  journal={ChemBioChem},
  pages={1242--1250},
  author={Dold, Jeremias E.G.A. and Pfotzer, Jessica and Späte, Anne-Katrin and Wittmann, Valentin}
}

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Bibliography of Konstanz

Yes