Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 48, Pages 11598-11610Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201701866
Keywords
carbohydrates; hydrogen bond; NMR spectroscopy; secondary structure; solution conformation
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Funding
- Swiss National Science Foundation (SNF sinergia grant) [CRSII3_127333]
- Swiss National Science Foundation (SNF) [CRSII3_127333] Funding Source: Swiss National Science Foundation (SNF)
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The increasing understanding of the essential role of carbohydrates in development, and in a wide range of diseases fuels a rapidly growing interest in the basic principles governing carbohydrate-protein interactions. A still heavily debated issue regarding the recognition process is the degree of flexibility or rigidity of oligosaccharides. Combining NMR structure determination based on extensive experimental data with DFT and database searches, we have identified a set of trisaccharide motifs with a similar conformation that is characterized by a non-conventional C-H center dot center dot center dot O hydrogen bond. These motifs are present in numerous classes of oligosaccharides, found in everything from bacteria to mammals, including Lewis blood group antigens but also unusual motifs from amphibians and marine invertebrates. The set of trisaccharide motifs can be summarized with the consensus motifs X-beta 1,4-[Fuc alpha 1,3]-Y and X-beta 1,3-[Fuc alpha 1,4]-Y-a secondary structure we name [3,4]F-branch. The wide spectrum of possible modifications of this scaffold points toward a large variety of glycoepitopes, which nature generated using the same underlying architecture.
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