Synthesis of tri-, penta-, and hepta-saccharides, functionalized with Orthogonally N-Protected Amino residues at the reducing and non-reducing ends
2012 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 68, no 33, 6712-6720 p.Article in journal (Refereed) Published
The synthesis of four bifunctionalized orthogonally N-protected oligosaccharides derived from lactose and mannose, intended as cross-linking derivatives, is described. The amino sugar at the non-reducing end is derivatized with an N-Boc-protected glycine moiety, and further connected to either a mannose (1→6) disaccharide or (1→3) lactose units (one, two or three) resulting in tri-, penta-, or heptasaccharides. All of the synthesized oligosaccharides have an Nbenzyloxycarbonyl-aminoethyl residue at the reducing end. The fully orthogonal N-Boc/N-Cbz protection group pattern enables further conjugation/derivatization and results in a hydrophilic cross-linking molecule. It was found that the order of the final synthetic steps were crucial to avoid acyl migration. A suitable amide coupling protocol has been applied to introduce the NBoc-protected glycine moiety in alcoholic solvent. The synthesized oligosaccharides will provide a model system to investigate the influence of length, structure and flexibility. The function of the cross-linked substituents thereby provide valuable insights into the role as a spacer molecule.
Place, publisher, year, edition, pages
2012. Vol. 68, no 33, 6712-6720 p.
Glycosylation, glycosidation, oligosaccharide synthesis, spacer molecules, orthogonally protected, carbohydrates, bifunctionalized
IdentifiersURN: urn:nbn:se:liu:diva-76730DOI: 10.1016/j.tet.2012.05.118ISI: 000306618400009OAI: oai:DiVA.org:liu-76730DiVA: diva2:516487