Topic
Trisaccharide
About: Trisaccharide is a research topic. Over the lifetime, 1553 publications have been published within this topic receiving 33290 citations. The topic is also known as: trisaccharides.
Papers published on a yearly basis
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Papers
TL;DR: It is found that when oligosaccharides containing reducing-terminal KDO residues are subjected to borohydride reduction prior to Smith degradation, the epimeric pair of oligosACcharides is obtained, containing 3-deoxy- L - ribo - and - arabino -hexonic acid at the end that had formerly been reducing.
Abstract: Publisher Summary This chapter examines the chemistry and biological significance of 3-deoxy- D -manno-2-octulosonic acid (KDO). The KDO occurs as a ketosidic component in all lipopolysaccharides (LPS) of Gram-negative bacteria and it has also been identified in several acidic exopolysaccharides. The incorporation of KDO appears to be a vital step in LPS biosynthesis and in the growth of the Gram-negative bacteria. The partial protection of individual KDO residues from periodate degradation, depending on the origin of the LPS and the method of TBA analysis, suggest that a common, branched, trisaccharide structure consisting of KDO residues might actually constitute the linkage region between core oligosaccharides and lipid A in LPS from Salmonella Minnesota . It is found that when oligosaccharides containing reducing-terminal KDO residues are subjected to borohydride reduction prior to Smith degradation, the epimeric pair of oligosaccharides is obtained, containing 3-deoxy- L - ribo - and - arabino -hexonic acid at the end that had formerly been reducing. The spectroscopic analysis of KDO and of its natural derivatives is also described in the chapter.
366 citations
TL;DR: Methyl triflate-promoted condensation of ethyl 4,6-O-benzylidene-2-deoxy- 2-phthalimido-1-thio-3-O gives a trisaccharide and a heptasaccharides derivative, respectively, which are parts of the complex type of glycoproteins.
359 citations
TL;DR: The thermodynamics of binding of concanavalin A with a series of linear and branched chain oligosaccharides including certain N-linked complex type and oligomannose type carbohydrates and a fraction of quail ovalbumin containing Man7 and Man8 oligomANNose chains have been determined using titration microcalorimetry.
Abstract: The thermodynamics of binding of concanavalin A (Con A) with a series of linear and branched chain oligosaccharides including certain N-linked complex type and oligomannose type carbohydrates and a fraction of quail ovalbumin containing Man7 and Man8 oligomannose chains have been determined using titration microcalorimetry. Methyl3,6-di-O-(alpha-D-mannopyranosyl)-alpha-D-mannopyranoside, a branch chain trisaccharide moiety found in all N-linked carbohydrates which possesses approximately 60-fold higher affinity than methyl alpha-D-mannopyranoside, exhibited a change in enthalpy of binding (delta H) of -14.4 kcal mol-1 as compared to -8.2 kcal mol-1 for the monosaccharide. This demonstrates that Con A possesses an extended binding site for the trimannoside. However, a biantennary complex type carbohydrate with terminal beta (1,2)-GlcNAc residues which binds with 3-fold higher affinity than the trimannoside possesses a delta H of only -10.6 kcal mol-1. A plot of -delta H versus -T delta S for the carbohydrates in the present study showed positive deviations in -T delta S for the complex type carbohydrate, as well as alpha (1,2)-di- and trimannosyl oligosaccharides which are part of the structures of oligomannose type carbohydrates. The relative favorable changes in binding entropies of these compounds are attributed to the presence of multiple internal and terminal residues in each molecule which can independently bind to the monosaccharide binding site of the lectin. The delta H values for the complex type carbohydrate and the alpha (1,2) mannose oligosaccharides were also approximately -2.5 kcal mol-1 greater than that of methyl alpha-D-mannopyranoside, indicating some extended binding site interactions.(ABSTRACT TRUNCATED AT 250 WORDS)
279 citations
240 citations
TL;DR: A general, modular strategy for the first completely stereoselective synthesis of defined heparin oligosaccharides is described, and the union of many glucosamine uronic acid disaccharide modules did not meet any problems, certain sequences proved not accessible.
Abstract: A general, modular strategy for the first completely stereoselective synthesis of defined heparin oligosaccharides is described. Six monosaccharide building blocks (four differentially protected glucosamines, one glucuronic and one iduronic acid) were utilized to prepare di- and trisaccharide modules in a fully selective fashion. Installation of the α-glucosamine linkage was controlled by placing a conformational constraint on the uronic acid glycosyl acceptors thereby establishing a new concept for stereochemical control. Combination of disaccharide modules to form trans-uronic acid linkages was completely selective by virtue of C2 participating groups. Coupling reactions between disaccharide modules exhibited sequence dependence. While the union of many glucosamine uronic acid disaccharide modules did not meet any problems, certain sequences proved not accessible. Elaboration of glucosamine uronic acid disaccharide building blocks to trisaccharide modules by addition of either one additional glucosamine or uronic acid allowed for stereoselective access to oligosaccharides as demonstrated on the example of a hexasaccharide resembling the ATIII-binding sequence. Final deprotection and sulfation yielded the fully synthetic heparin oligosaccharides.
229 citations
Related Topics (5)
Performance Metrics
| Year | Papers |
|---|---|
| 2025 | 9 |
| 2024 | 25 |
| 2023 | 26 |
| 2022 | 41 |
| 2021 | 14 |
| 2020 | 21 |