1334540-38-3Relevant academic research and scientific papers
Oligosaccharides and oligosaccharides-protein conjugates derived from clostridium difficile polysaccharide PS-I, methods of synthesis and uses thereof, in particular as vaccines and diagnostic tools
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, (2013/03/26)
The invention relates to a synthetic oligosaccharide representing part of the repeating unit of the Clostridium difficile glycopolymer PS-I and having the sequence of the pentasaccharide α-L-Rhap-(1→3)-β-D-Glcp-(1→4)-[α-L-Rhap-(1→3)]-α-D-Glcp-(1→2)-α-D-Glcp or a synthetic fragment or derivative thereof. Preferably, the claimed synthetic oligosaccharide bears at least one linker L for conjugation to a carrier protein or for immobilization on a surface. Further aspects of the invention relate to advantageous methods for synthesizing said synthetic oligosaccharide and oligosaccharide-protein conjugate as well as to uses thereof, in particular as vaccines and diagnostic tools. A preferred method for synthesizing the pentasaccharide is shown below.
Automated solid-phase synthesis of a β-(1,3)-glucan dodecasaccharide
Weishaupt, Markus W.,Matthies, Stefan,Seeberger, Peter H.
, p. 12497 - 12503 (2013/09/23)
β-Glucans are a group of structurally heterogeneous polysaccharides found in bacteria, fungi, algae and plants. β-(1,3)-D-Glucans have been studied in most detail due to their impact on the immune system of vertebrates. The studies into the immunomodulatory properties of these glucans are typically carried out with isolates that contain a heterogeneous mixture of polysaccharides of different chain lengths and varying degrees of branching. In order to determine the structure-activity relationship of β-(1,3)-glucans, access to homogeneous, structurally-defined samples of these oligosaccharides that are only available through chemical synthesis is required. The syntheses of β-glucans reported to date rely on the classical solution-phase approach. We describe the first automated solid-phase synthesis of a β-glucan oligosaccharide that was made possible by innovating and optimizing the linker and glycosylating agent combination. A β-(1,3)-glucan dodecasaccharide was assembled in 56 h in a stereoselective fashion with an average yield of 88 % per step. This automated approach provides means for the fast and efficient assembly of linker-functionalized mono- to dodecasaccharide β-(1,3)-glucans required for biological studies. β-Glucans are a group of structurally heterogeneous polysaccharides found in bacteria, fungi, algae and plants. The first automated solid-phase synthesis of a β-glucan oligosaccharide is reported. A β-(1,3)-glucan dodecasaccharide was assembled in 56 h in a stereoselective fashion with an average yield of 88 % per step (see scheme; Fmoc = 9-fluorenylmethoxycarbonyl, PIV = pivaloyl). Copyright
Progress toward developing a carbohydrate-conjugate vaccine against Clostridium difficile ribotype 027: Synthesis of the cell-surface polysaccharide PS-I repeating unit
Martin, Christopher E.,Weishaupt, Markus W.,Seeberger, Peter H.
, p. 10260 - 10262 (2011/10/19)
Clostridium difficile strain ribotype 027 is a hypervirulent pathogen that is responsible for recent, severe outbreaks of serious nosocomial infections. As a foundation for the development of a preventative carbohydrate-based vaccine, we have synthesized a pentasaccharide cell wall repeating unit from PS-I unique to this strain, by the linear assembly of four monosaccharide building blocks.
