Issue 17, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Chemoenzymic synthesis of oligosaccharide fragments of the capsular polysaccharide of Streptococcus pneumoniae type 14

Dirk Michalik,†a   Johannes F. G. Vliegentharta  and  Johannis P. Kamerling*a  

* Corresponding authors

a Bijvoet Center, Department of Bio-Organic Chemistry, Section of Glycoscience and Biocatalysis, Utrecht University, Padualaan 8, NL-3584 CH Utrecht, The Netherlands

Abstract

The chemoenzymic synthesis is described of β-D-Galp-(1→4)-β-D-Glcp-(1→6)-[(β-D-Galp)-(1→4)]-β-D-GlcpNAc-(1→3)-β-D-Galp-(1→O(CH2)6NH2) 20 and β-D-Galp-(1→4)-β-D-Glcp-(1→6)-[(β-D-Galp)-(1→4)]-β-D-GlcpNAc-(1→3)-β-D-Galp-(1→4)-β-D-Glcp-(1→O(CH2)6NH2) 21, representing penta- and hexasaccharide fragments of the Streptococcus pneumoniae type 14 capsular polysaccharide. In a chemical approach the intermediate tetra- and pentasaccharide fragments 18 and 19, respectively, were synthesised, wherein the non-terminal N-acetyl-β-D-glucosamine residues were not yet galactosylated. Both intermediates were found to be good acceptor substrates for bovine milk β-1,4-galactosyltransferase. The title oligosaccharides form suitable compounds for conjugation with carrier proteins, to be tested as potential vaccines in animal models.

Graphical abstract: Chemoenzymic synthesis of oligosaccharide fragments of the capsular polysaccharide of Streptococcus pneumoniae type 14

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/B204933C
Article type
Paper
Submitted
22 May 2002
Accepted
16 Jul 2002
First published
13 Aug 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1973-1981

Permissions

Request permissions

Chemoenzymic synthesis of oligosaccharide fragments of the capsular polysaccharide of Streptococcus pneumoniae type 14

D. Michalik, J. F. G. Vliegenthart and J. P. Kamerling, J. Chem. Soc., Perkin Trans. 1, 2002, 1973 DOI: 10.1039/B204933C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements