Synthesis of Functionalised Nucleosides for Incorporation into Nucleic Acid-Based Serine Protease Mimics

Abstract

Abstract:The synthesis of nucleosides modified with an extra imidazole, carboxyl and hydroxyl group is described. These nucleosides can be incorporated into an oligonucleotide duplex, thus generating a novel type of serine protease mimic.

Chemical Synthesis of Site‐Specifically 2′‐Azido‐Modified RNA and Potential Applications for Bioconjugation and RNA Interference

“…[ 13 ] Subsequently, the 5′-hydroxyl group was protected as dimethoxytrityl (DMT) ether to form compound 5 . [ 14 ] Conversion into the corresponding phosphodiester 1 was achieved in good yield by reaction with in situ-generated 2-chlorophenyl chlorophosphorotriazolide, analogously to a general procedure in the literature. [ 15 ]…”

Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction

“…We here illustrated the efficient application of a simple carboxamidation procedure for the synthesis of modified nucleosides featuring two extra functional groups. Because hydrolysis of the methyl ester and removal of the t- Boc is performed during the standard cleavage of solid support using NH 4 OH and benzyl and benzoyl protecting groups can be removed by hydrogenation [ 64 ], only one extra deprotection step is needed after incorporation. After transformation of the modified nucleosides into the corresponding phosphoramidite building blocks 5 , 9 and 13 are amenable to incorporation in nucleic acids through standard DNA synthesis methodology.…”

Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction

“…This reaction has been the dominant method for the preparation of pyrimidine, purine and other heterocyclic nucleosides. Despite these available methods [ 8 , 9 , 27 , 28 , 29 , 30 ], a facile and green synthetic strategy, which avoids the use of costly and hazardous catalysts, for synthesizing nucleosides remains an urgent need.…”