Automated synthesis of sialylated oligosaccharides

• Davide Esposito,
• Mattan Hurevich,
• Bastien Castagner,
• Cheng-Chung Wang and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2012, 8, 1601–1609, doi:10.3762/bjoc.8.183

• ; sialosides; Introduction Sialic acid (Sia) belongs to a family of nonulosonic acids, i.e., monosaccharides equipped with a carboxylic moiety and a nine-carbon backbone, which play a unique role in glycobiology. Sia-containing glycans mediate pathogen invasion [1] and are involved in signalling cascades

• antigens in antibody selection by phage-display methods [31]. Thus, trisaccharide 16 (Scheme 7) was reacted with biotin derivative 31 in PBS buffer to afford compound 32 in 80% yield after gel filtration. Conclusion The synthesis of sialosides is important to create tools for glycobiology. The work

The use of glycoinformatics in glycochemistry

• Thomas Lütteke

Beilstein J. Org. Chem. 2012, 8, 915–929, doi:10.3762/bjoc.8.104

• that it provides information on proteins to which specific glycans were found to be attached, including details on glycosylation sites. The Japan Consortium for Glycobiology and Glycotechnology DataBase (JCGGDB) [34] provides a collection of individual databases that are cross-linked with each other

2-Allylphenyl glycosides as complementary building blocks for oligosaccharide and glycoconjugate synthesis

• Hemali D. Premathilake and
• Alexei V. Demchenko

Beilstein J. Org. Chem. 2012, 8, 597–605, doi:10.3762/bjoc.8.66

• efficient oligosaccharide assembly. Keywords: carbohydrates; glycosylation; leaving group; oligosaccharides; orthogonal strategy; selective activation; Introduction Current knowledge about the key roles of carbohydrates is still limited. However, thanks to the explosive growth of the field of glycobiology

Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays

• Ian Cumpstey,
• Jens Frigell,
• Elias Pershagen,
• Tashfeen Akhtar,
• Elena Moreno-Clavijo,
• Inmaculada Robina,
• Dominic S. Alonzi and
• Terry D. Butters

Beilstein J. Org. Chem. 2011, 7, 1115–1123, doi:10.3762/bjoc.7.128

• National de la Recherche Scientifique, 91198 Gif-sur-Yvette CEDEX, France Department of Organic Chemistry, Faculty of Chemistry, University of Seville, Prof. García González, 1, 41012 Seville, Spain Glycobiology Institute, Department of Biochemistry, Oxford University, South Parks Road, Oxford, OX1 3QU

• . Supporting Information File 214: 1H and 13C NMR spectra of compounds 18–27. Acknowledgements IC acknowledges the support of Vetenskapsrådet (the Swedish Research Council). TDB and DSA acknowledge the support of the Glycobiology Institute and Grant No. R01CA125642 from the National Cancer Institute for part

(Pseudo)amide-linked oligosaccharide mimetics: molecular recognition and supramolecular properties

• José L. Jiménez Blanco,
• Fernando Ortega-Caballero,
• Carmen Ortiz Mellet and
• José M. García Fernández

Beilstein J. Org. Chem. 2010, 6, No. 20, doi:10.3762/bjoc.6.20

• oligosaccharides is not yet efficient enough for generating oligosaccharide-based libraries that may be useful in the future for the discovery of new therapeutic drugs. Taking into account the increasing importance of glycobiology and the difficulties associated to the synthesis of carbohydrate-based libraries