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1 article(s) from Weishaupt, Markus W

Automated glycan assembly of a S. pneumoniae serotype 3 CPS antigen

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

Beilstein J. Org. Chem. 2016, 12, 1440–1446, doi:10.3762/bjoc.12.139

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Graphical Abstract

Figure 1: Disaccharide repeating unit of the S. pneumoniae serotype 3 CPS.

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Figure 2: Building blocks and solid support for the automated solid-phase synthesis of S. pneumoniae serotype...

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Scheme 1: Attempted assembly of SP3 trisaccharide 5 using glycosyl phosphate building blocks 1 and 2. Reagent...

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Figure 3: HPLC chromatogram of the crude products of the attempted AGA of SP3 trisaccharide 5; conditions: YM...

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Scheme 2: Attempted AGA of SP3 trisaccharide 9 using glycosyl phosphate building blocks 1 and 3. Reagents and...

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Figure 4: HPLC chromatogram of the crude products of the attempted AGA of SP3 trisaccharide 9; conditions: YM...

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Scheme 3: Automated synthesis of linker-bound glucuronic acid 10 using glycosyl phosphate building block 1. R...

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Scheme 4: Automated synthesis of SP3 trisaccharide 5 using glycosyl phosphate building blocks 1 and 2. Reagen...

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Figure 5: HPLC chromatogram of the crude products of the automated solid-phase SP3 trisaccharide 5 synthesis;...

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Scheme 5: Global deprotection of SP3 trisaccharide 5. Reagents and conditions: a) LiOH, H₂O₂, THF, −5 °C to r...

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Published 12 Jul 2016

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