Abstract
Methods for the chemical synthesis of RNA have been available for almost half century, and presently, RNA could be chemically synthesized by automated synthesizers, using protected ribonucleosides preactivated as phosphoramidites, which has already been covered by many reviews. In addition to advancement on synthetic methods, a variety of modifications have also been made on the synthesized oligonucleotides, and previous reviews on the general synthesis of RNAs have not covered this area. In this tutorial review, three types of modifications have been summarized standing at the viewpoint of medicinal chemistry: (1) modifications on nucleobase, comprising substituent introduction and replacement with pseudobase; (2) modifications on ribose, consisting of modifications on the 2’, 3’ or 5’-position, alternation of configuration, and conformational restriction on ribose; (3) modifications on internucleoside linkages, including amide, formacetal, sulfide, sulfone, ether, phosphorothiolate and phosphorothioate linkages. Synthetic methods achieving these modifications along with the functions or values of these modifications have also been discussed and commented on.
Keywords: Bioactive RNAs, small non-coding RNA, oligoribonucleotide, structural modification, chemical synthesis, nucleobase, pseudobase, ribose, conformational restriction, internucleoside linkage.
Current Medicinal Chemistry
Title:Advances in Chemical Synthesis of Structurally Modified Bioactive RNAs
Volume: 20 Issue: 29
Author(s): Ziyuan Li, Haipin Zhou, Xiaoming Wu and Hequan Yao
Affiliation:
Keywords: Bioactive RNAs, small non-coding RNA, oligoribonucleotide, structural modification, chemical synthesis, nucleobase, pseudobase, ribose, conformational restriction, internucleoside linkage.
Abstract: Methods for the chemical synthesis of RNA have been available for almost half century, and presently, RNA could be chemically synthesized by automated synthesizers, using protected ribonucleosides preactivated as phosphoramidites, which has already been covered by many reviews. In addition to advancement on synthetic methods, a variety of modifications have also been made on the synthesized oligonucleotides, and previous reviews on the general synthesis of RNAs have not covered this area. In this tutorial review, three types of modifications have been summarized standing at the viewpoint of medicinal chemistry: (1) modifications on nucleobase, comprising substituent introduction and replacement with pseudobase; (2) modifications on ribose, consisting of modifications on the 2’, 3’ or 5’-position, alternation of configuration, and conformational restriction on ribose; (3) modifications on internucleoside linkages, including amide, formacetal, sulfide, sulfone, ether, phosphorothiolate and phosphorothioate linkages. Synthetic methods achieving these modifications along with the functions or values of these modifications have also been discussed and commented on.
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Cite this article as:
Li Ziyuan, Zhou Haipin, Wu Xiaoming and Yao Hequan, Advances in Chemical Synthesis of Structurally Modified Bioactive RNAs, Current Medicinal Chemistry 2013; 20 (29) . https://dx.doi.org/10.2174/0929867311320290010
DOI https://dx.doi.org/10.2174/0929867311320290010 |
Print ISSN 0929-8673 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-533X |
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