title: Defined presentation of carbohydrates on a duplex DNA scaffold.
abstract: A new method for the spatially defined alignment of carbohydrates on a duplex DNA scaffold is presented. The use of an N-hydroxysuccinimide (NHS)-ester phosphoramidite along with carbohydrates containing an alkylamine linker allows for on-column labeling during solid-phase oligonucleotide synthesis. This modification method during solid-phase synthesis only requires the use of minimal amounts of complex carbohydrates. The covalently attached carbohydrates are presented in the major groove of the B-form duplex DNA as potential substrates for murine type II C-type lectin receptors mMGL1 and mMGL2. CD spectroscopy and thermal melting revealed only minimal disturbance of the overall helical structure. Surface plasmon resonance and cellular uptake studies with bone-marrow-derived dendritic cells were used to assess the capability of these carbohydrate-modified duplexes to bind to mMGL receptors.
authors: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany.
authors: Mark K
authors: MK
authors: Schlegel
authors: Julia
authors: J
authors: Hütter
authors: Magdalena
authors: M
authors: Eriksson
authors: Bernd
authors: B
authors: Lepenies
authors: Peter H
authors: PH
authors: Seeberger
mesh_terms: D001483:Base Sequence; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D017931:DNA Primers; D008969:Molecular Sequence Data; D021241:Spectrometry, Mass, Electrospray Ionization; D020349:Surface Plasmon Resonance
chemical_list: D002241:Carbohydrates; D017931:DNA Primers; D004247:DNA