Synthesis of Pseudooligosaccharides Related to the Capsular Phosphoglycan of Type .

Synthesis of spacer-armed pseudodi-, pseudotetra-, and pseudohexasaccharides related to the capsular phosphoglycan of type , the second most virulent serotype of (after type ), was performed for the first time via iterative chain elongation using H-phosphonate chemistry for the formation of inter-unit phosphodiester bridges. These compounds were prepared for the design of neoglycoconjugates, as exemplified by the transformation of the obtained pseudohexasaccharide derivative into a biotinylated glycoconjugate suitable for use in immunological studies, particularly in diagnostic screening systems as a coating antigen for streptavidin-coated plates and chip slides.

Cross reacting material (CRM197) as a carrier protein for carbohydrate conjugate vaccines targeted at bacterial and fungal pathogens.

This paper gives an overview of conjugate glycovaccines which contain recombinant diphtheria toxoid CRM197 as a carrier protein. A special focus is given to synthetic methods used for preparation of neoglycoconjugates of CRM197 with oligosaccharide epitopes of cell surface carbohydrates of pathogenic bacteria and fungi. Syntheses of commercial vaccines and laboratory specimen on the basis of CRM197 are outlined briefly.

Glycoconjugate Vaccines for Prevention of Type b Diseases.

This review summarizes the experience in laboratory- and industrial-scale syntheses of glycoconjugate vaccines used for prevention of infectious diseases caused by type b bacteria based on the linear capsular polysaccharide poly-3-β-D-ribosyl-(1→1)-D-ribitol-5-phosphate (PRP) or related synthetic oligosaccharide ligands. The methods for preparation of related oligosaccharide derivatives and results of the studies evaluating effect of their length on immunogenic properties of the conjugates with protein carriers are overviewed.

High-resolution electrospray mass spectra of hexaethylene glycol connected biotinylated HNK-1 antigenic trisaccharide molecular probe and its non-sulfated analogue.

High-resolution electrospray mass spectra in positive and negative ion modes (MS and MS/MS) were measured and described for biotinylated hexaethylene glycol (HEG) connected molecular probes bearing HNK-1 (abbreviation of human natural killer cell-1 epitope) antigenic trisaccharide (1) and its non-sulfated analogue (2). For molecular probe 2, in its CID MS/MS of [M+2Na](2+), unexpected peak at m/z 530.2475 [C22H41N3O8SNa](+) was observed and attributed to the fragmentation of the aglycone at the end of the HEG chain distant from the biotin fragment.

Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel.

Two new triterpenoid saponins 1 and 2 were isolated from the methanol extract of the roots of Acanthophyllum gypsophiloides Regel. These saponins have quillaic acid or gypsogenin moieties as an aglycon, and both bear similar sets of two oligosaccharide chains, which are 3-O-linked to the triterpenoid part trisaccharide α-L-Arap-(1→3)-[α-D-Galp-(1→2)]-β-D-GlcpA and pentasaccharide β-D-Xylp-(1→3)-β-D-Xylp-(1→3)-α-L-Rhap-(1→2)-[β-D-Quip-(1→4)]-β-D-Fucp connected through an ester linkage to C-28. The structures of the obtained saponins were elucidated by a combination of mass spectrometry and 2D NMR spectroscopy.