Herein we present a versatile synthetic method for the 8-thioalkylation of (deoxy)adenosine with a short carbon linker having on the other side a variety of mols. (psoralen, acridine) and functional groups (alkyne). After conventional protections, the modified adenosine can be phosphytylated and inserted into an oligonucleotide without affecting the std. protocols for supported oligonucleotide synthesis. The hybridization properties of a generic oligonucleotide contg. the above conjugated moieties toward both DNA and RNA are evaluated both in the case of a perfectly complementary strand and in the case of a single mismatch. This methodol. is suitable for the prepn. of several types of derivs. and-through the alkynyl moiety-provides fast access to click-chem. transformations.
Labeling Deoxyadenosine for the Preparation of Functional Conjugated Oligonucleotides
MARCHESI, Elena;PERRONE, Daniela;
2013
Abstract
Herein we present a versatile synthetic method for the 8-thioalkylation of (deoxy)adenosine with a short carbon linker having on the other side a variety of mols. (psoralen, acridine) and functional groups (alkyne). After conventional protections, the modified adenosine can be phosphytylated and inserted into an oligonucleotide without affecting the std. protocols for supported oligonucleotide synthesis. The hybridization properties of a generic oligonucleotide contg. the above conjugated moieties toward both DNA and RNA are evaluated both in the case of a perfectly complementary strand and in the case of a single mismatch. This methodol. is suitable for the prepn. of several types of derivs. and-through the alkynyl moiety-provides fast access to click-chem. transformations.I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
