Abstract:
In this study, an efficient methodology for the preparation of carbohydrate-RNA
conjugates was established, which involved the use of 3,4~diethoxy-3-cyclobutene-l,2-
dione (diethyl squarate) as the linking reagent. First, a glycan moiety containing an
amino group reacted with diethyl squarate to form an activated glycan, which further
reacted with an amino modified oligoribonucleotide to form a glycoconjugate under
slightly basic conditions. The effect of glycosylation on the stability of RNA molecules
was evaluated on two glycoconjugates, monomannosyl UlO-mer and dimannosyl UlO-mer.
In the synthesis of aromatic fluorescent ribosides, perbenzylated ribofuranosyl pyrene
and phenanthrene were synthesized from perbenzylated ribolactone. Deprotection of
benzyl-protected ribofuranosyl phenanthrene and pyrene by boron tribromide gave
ribofuranosyl phenanthrene and ribopyranosyl pyrene, respectively. UV/vis and
fluorescent properties of the ribosides were characterized.
