title: Stereoselective synthesis of light-activatable perfluorophenylazide-conjugated carbohydrates for glycoarray fabrication and evaluation of structural effects on protein binding by SPR imaging.
abstract: A series of light-activatable perfluorophenylazide (PFPA)-conjugated carbohydrate structures have been synthesized and applied to glycoarray fabrication. The glycoconjugates were structurally varied with respect to anomeric attachment, S-, and O-linked carbohydrates, respectively, as well as linker structure and length. Efficient stereoselective synthetic routes were developed, leading to the formation of the PFPA-conjugated structures in good yields over few steps. The use of glycosyl thiols as donors proved especially efficient and provided the final compounds in up to 70% total yield with high anomeric purities. PFPA-based photochemistry was subsequently used to generate carbohydrate arrays on a polymeric surface, and surface plasmon resonance imaging (SPRi) was applied for evaluation of carbohydrate-protein interactions using the plant lectin Concanavalin A (Con A) as a probe. The results indicate better performance and equal efficiency of S- and O-linked structures with intermediate linker length.
authors.affiliation: Department of Chemistry, KTH-Royal Institute of Technology, Teknikringen 30, S-10044, Stockholm, Sweden.
authors.forename: Lingquan
authors.initials: L
authors.lastname: Deng
authors.forename: Oscar
authors.initials: O
authors.lastname: Norberg
authors.forename: Suji
authors.initials: S
authors.lastname: Uppalapati
authors.forename: Mingdi
authors.initials: M
authors.lastname: Yan
authors.forename: Olof
authors.initials: O
authors.lastname: Ramström
mesh_terms: D001386:Azides / Q000138:chemical synthesis*; D002241:Carbohydrates / Q000138:chemical synthesis*; D017611:Fluorine Compounds / Q000138:chemical synthesis*; D046228:Microarray Analysis; D015394:Molecular Structure; D011485:Protein Binding; D011506:Proteins / Q000032:analysis* / Q000378:metabolism; D013237:Stereoisomerism; D020349:Surface Plasmon Resonance
chemical_list: D001386:Azides; D002241:Carbohydrates; D017611:Fluorine Compounds; D011506:Proteins