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Medientyp:
E-Artikel
Titel:
Defined Presentation of Carbohydrates on a Duplex DNA Scaffold
Beteiligte:
Schlegel, Mark K.;
Hütter, Julia;
Eriksson, Magdalena;
Lepenies, Bernd;
Seeberger, Peter H.
Erschienen:
Wiley, 2011
Erschienen in:ChemBioChem
Sprache:
Englisch
DOI:
10.1002/cbic.201100511
ISSN:
1439-4227;
1439-7633
Entstehung:
Anmerkungen:
Beschreibung:
<jats:title>Abstract</jats:title><jats:p>A new method for the spatially defined alignment of carbohydrates on a duplex DNA scaffold is presented. The use of an<jats:italic>N</jats:italic>‐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.</jats:p>