Automated glycan assembly of a s. pneumoniae serotype 3 cps antigen

Markus W. Weishaupt, Stefan Matthies, Mattan Hurevich, Claney L. Pereira, Heung Sik Hahm, Peter H. Seeberger*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

19 Scopus citations


Vaccines against S. pneumoniae, one of the most prevalent bacterial infections causing severe disease, rely on isolated capsular polysaccharide (CPS) that are conjugated to proteins. Such isolates contain a heterogeneous oligosaccharide mixture of different chain lengths and frame shifts. Access to defined synthetic S. pneumoniae CPS structures is desirable. Known syntheses of S. pneumoniae serotype 3 CPS rely on a time-consuming and low-yielding late-stage oxidation step, or use disaccharide building blocks which limits variability. Herein, we report the first iterative automated glycan assembly (AGA) of a conjugation-ready S. pneumoniae serotype 3 CPS trisaccharide. This oligosaccharide was assembled using a novel glucuronic acid building block to circumvent the need for a late-stage oxidation. The introduction of a washing step with the activator prior to each glycosylation cycle greatly increased the yields by neutralizing any residual base from deprotection steps in the synthetic cycle. This process improvement is applicable to AGA of many other oligosaccharides.

Original languageAmerican English
Pages (from-to)1440-1446
Number of pages7
JournalBeilstein Journal of Organic Chemistry
StatePublished - 12 Jul 2016
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2016 Weishaupt et al.; licensee Beilstein-Institut.


  • Automation
  • Glycosylation
  • Oligosaccharides
  • Protecting groups
  • Solid-phase synthesis
  • Streptococcus pneumoniae


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