Konformationsanalyse, XXV. Konformationen von Octasaccharid‐ und Pentasaccharid‐Sequenzen in N‐Glycoproteinen des Lactosamin‐Typs

Paulsen, Hans; Peters, Thomas; Sinnwell, Volker; Lebuhn, Rolf; Meyer, Bernd

doi:10.1002/jlac.198519850309

Cited by 47 publications

(22 citation statements)

References 18 publications

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“…[64,651 The result is presented in Figure 6a.r643 The pentasaccharide chain with linkages to the secondary hydroxy groups of the (1 + 3)-arm shows the expected preferred conformation. The side chain of the (1 --+ 6)-arm is also inclined towards the reducing GlcNAc unit, as in 16.…”

Section: Conformation Of the Lactosamine-type Structure And Comparisomentioning

confidence: 91%

Syntheses, Conformations and X‐Ray Structure Analyses of the Saccharide Chains from the Core Regions of Glycoproteins

Paulsen¹

1990

Angew. Chem. Int. Ed. Engl.

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243

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The covalently bound carbohydrate moiety in glycoproteins can stabilize the protein molecule intramolecularly, or it may have an intermolecular function as receptor in biological recognition. The discovery of these biological phenomena has led to a renaissance of the chemistry and biochemistry of carbohydrates. Both N‐glycoproteins as well as O‐glycoproteins contain special, invariant oligosaccharide chains in the protein‐binding region, which occur again in all glycoproteins, and are described as the “core regions.” This review describes the various methods of oligosaccharide synthesis that may be used to arrive at the basic core structures by chemical means. Methods of oligosaccharide synthesis have improved so much that it is possible to synthesize complex lactosamine‐type structures, and “bisected”‐type structures up to nona‐ and undecasaccharides respectively. Oligosaccharide chains are considerably less flexible than peptide chains. Using modern methods of NMR spectroscopy, their preferred solution conformation can readily be determined. In the case of one branched octasaccharide, a comparison of the conformations in solution and in the crystal is possible. Oligosaccharides may be linked to the amide group of an asparagine, or to the hydroxyl groups of serine or threonine. By using suitable protecting groups, the glycosyl amino acids obtained can be extended with further amino acids at the N‐ or C‐terminus, thus arriving at the desired glycopeptide sequences. In the linkage region, glycopeptides prefer certain conformations. Future research into glycoprotein functions may involve the synthesis and biochemical study of modified glycoprotein segments.

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Section: Conformation Of the Lactosamine-type Structure And Comparisomentioning

confidence: 91%

Syntheses, Conformations and X‐Ray Structure Analyses of the Saccharide Chains from the Core Regions of Glycoproteins

Paulsen¹

1990

Angew. Chem. Int. Ed. Engl.

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243

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“…This perception is based on the observations that the al-6 bond of di-or tri-antennary oligosaccharides is flexible [240][241][242][243][244][245][246] and that analytical centrifugation of native and deglycosylated hormones revealed essentially no difference in sedimentation constant [247].…”

Section: Final Comments and Future Developmentsmentioning

confidence: 99%

Molecular structures of glycoprotein hormones and functions of their carbohydrate components

Hartree

Renwick

1992

Biochemical Journal

146

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“…The conformation of these and other relevant oligosaccharides has been calculated with the semi-empiric geometry of saccharides (GESA) program (Paulsen et al, 1985). Table 1.…”

Section: Introductionmentioning

confidence: 99%

Studies of the binding activity of phage G13 to synthetic trisaccharides analogous to binding structures in Salmonella typhimurium and Escherichia coli C core saccharide. Correlation between conformation and binding activity

Bruse

Wollin²,

Oscarson

et al. 1991

J of Molecular Recognition

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Phage G13 binds to the carbohydrate part of lipopolysaccharides from rough mutants of Salmonella and Escherichia coli as the first event of infection. Equilibrium dialysis inhibition studies with native and synthetic trisaccharides as inhibitors suggested that phage G13 recognizes branched oligosaccharides having 6-O-alpha- or 7-O-alpha-glycosyl groups with alpha-Man(1----3) [alpha-Man(1----6)]Man (Man[Man]Man) and alpha-Glc(1----3)-[alpha-Hep(1----7)] alpha-Hep(1----3) alpha-Hep(1----5)Kdo as the smallest saccharides with inhibitory activity (Wollin et al., 1989). Of four synthetic analogues to Man[Man]Man only Man(1----3)[alpha-Gal(1----6)]alpha-Man-OMe (Man[Gal]-Man) and alpha-Glc(1----3)[alpha-Hep(1----7)]alpha-Hep-OMe (Glc[Hep]Hep) inhibited the binding of labelled E. coli C core nonasaccharide ligand to G13 with activities which were 10- and 15-fold lower than Man[Man]Man. The trisaccharides alpha-Man(1----3)[alpha-Glc(1----6)[alpha-Man-OMe (Man[Glc]Mann) and alpha-Man(1---3)[alpha-Tal(1----6)]alpha-Man-OMe (Man[Tal]Man) showed no inhibition at concentrations 75-fold higher than Man[Man]Man. Minimum energy conformation calculations of the saccharides using the GESA method showed that the 6-O-alpha-Man group in Man[Man]Man and the 7-O-alpha-Hep group SL805 pentasaccharide expose their OH-2 and OH-3 groups in a similar way and these are postulated to be key structural features for binding activity. The importance of hydroxy groups at certain positions is implied from the fact that both manno- and galacto-isomers are active. We also conclude that the O6-C6-C5-O5-C1 region of the 3-O-alpha-glycosyl group in the Man[Man]Man trisaccharide, or part of it, is important for the G13 binding activity.

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Konformationsanalyse, XXV. Konformationen von Octasaccharid‐ und Pentasaccharid‐Sequenzen in N‐Glycoproteinen des Lactosamin‐Typs

Cited by 47 publications

References 18 publications

Syntheses, Conformations and X‐Ray Structure Analyses of the Saccharide Chains from the Core Regions of Glycoproteins

Syntheses, Conformations and X‐Ray Structure Analyses of the Saccharide Chains from the Core Regions of Glycoproteins

Molecular structures of glycoprotein hormones and functions of their carbohydrate components

Studies of the binding activity of phage G13 to synthetic trisaccharides analogous to binding structures in Salmonella typhimurium and Escherichia coli C core saccharide. Correlation between conformation and binding activity

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