Synthesis of a hexasaccharide fragment of group E streptococci polysaccharide and the tetrasaccharide repeating unit of E. coli O7:K98:H6

Zeng, Youlin; Kong, Fanzuo

doi:10.1016/j.carres.2004.03.027

Cited by 3 publications

References 17 publications

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The Cyanopivaloyl Ester: A Protecting Group in the Assembly of Oligorhamnans

et al. 2016

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Protecting groups play a vital role in the assembly of oligosaccharides. The pivaloyl (Piv) ester is commonly used to ensure 1,2‐trans‐selective glycosylation reactions. A significant drawback of the Piv ester is its stability, necessitating strong alkaline conditions for its removal. We here present the cyanopivaloyl (CNPiv) group, a modified pivaloyl group having a cyano group appended to the tert‐butyl moiety. The CNPiv group benefits from the profitable features of the Piv group (stability and effective neighboring‐group participation with minimal orthoester formation during glycosylation reactions), but can be removed under mild conditions (reduction of the cyano function followed by mild base treatment). The applicability of the CNPiv group is demonstrated in the assembly of two rhamnose oligosaccharides, a hexarhamnan that represents a fragment of the capsular polysaccharide of Enterococcus faecium and a tetrarhamnan that is part of the polyrhamnose backbone of the Lancefield Group A carbohydrate (GAC).

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The Cyanopivaloyl Ester: A Protecting Group in the Assembly of Oligorhamnans

et al. 2016

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2003–2004

Harvey

2008

Mass Spectrometry Reviews

100

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This review is the third update of the original review, published in 1999, on the application of matrix-assisted laser desorption/ionization (MALDI) mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings the topic to the end of 2004. Both fundamental studies and applications are covered. The main topics include methodological developments, matrices, fragmentation of carbohydrates and applications to large polymeric carbohydrates from plants, glycans from glycoproteins and those from various glycolipids. Other topics include the use of MALDI MS to study enzymes related to carbohydrate biosynthesis and degradation, its use in industrial processes, particularly biopharmaceuticals and its use to monitor products of chemical synthesis where glycodendrimers and carbohydrate-protein complexes are highlighted.

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Chapter 6 Stereocontrolled Synthesis of Mannans and Rhamnans

Cai

Crich

2009

Advances in Carbohydrate Chemistry and Biochemistry

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Synthesis of a hexasaccharide fragment of group E streptococci polysaccharide and the tetrasaccharide repeating unit of E. coli O7:K98:H6

Cited by 3 publications

References 17 publications

The Cyanopivaloyl Ester: A Protecting Group in the Assembly of Oligorhamnans

The Cyanopivaloyl Ester: A Protecting Group in the Assembly of Oligorhamnans

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2003–2004

Chapter 6 Stereocontrolled Synthesis of Mannans and Rhamnans

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