Suppr超能文献

α-核苷综述:从发现、合成到性质及潜在应用

Review of α-nucleosides: from discovery, synthesis to properties and potential applications.

作者信息

Ni Guangcheng, Du Yuqi, Tang Fan, Liu Jiang, Zhao Hang, Chen Qianming

机构信息

State Key Laboratory of Oral Diseases, National Clinical Research Center for Oral Diseases, Chinese Academy of Medical Sciences Research Unit of Oral Carcinogenesis and Management, West China Hospital of Stomatology, Sichuan University Chengdu Sichuan 610041 P. R. China

出版信息

RSC Adv. 2019 May 7;9(25):14302-14320. doi: 10.1039/c9ra01399g.

Abstract

Nucleic acids play an important role in the genetic process of organisms; nucleosides, the building block of nucleic acids, typically exist in nature in a β configuration. As an anomer of β-nucleoside, α-nucleoside is extremely rare in nature. Because of their unique and interesting properties such as high stability, specific parallel double-stranded structure and some other biochemical properties, α-nucleosides have attracted wide attention. Various methods including but not limited to the mercuri procedure, fusion reaction and Vorbrüggen glycosylation have been used to synthesize α-nucleosides and their derivatives. However, to the best of our knowledge, there is no review that has summarized these works. Therefore, we systematically review the discovery, synthesis, properties, and potential applications of α-nucleosides in this article and look to provide a reference for subsequent studies in the coming years.

摘要

核酸在生物体的遗传过程中起着重要作用;核苷作为核酸的组成单元,通常以β构型存在于自然界中。作为β-核苷的端基异构体,α-核苷在自然界中极为罕见。由于其具有诸如高稳定性、特定的平行双链结构以及其他一些生化特性等独特且有趣的性质,α-核苷已引起广泛关注。包括但不限于汞法、融合反应和 Vorbruggen 糖基化等各种方法已被用于合成α-核苷及其衍生物。然而,据我们所知,尚无综述对这些工作进行总结。因此,我们在本文中系统地综述了α-核苷的发现、合成、性质及潜在应用,以期为未来几年的后续研究提供参考。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4daa/9064229/af1b34ebcd19/c9ra01399g-f2.jpg

相似文献

1
Review of α-nucleosides: from discovery, synthesis to properties and potential applications.
RSC Adv. 2019 May 7;9(25):14302-14320. doi: 10.1039/c9ra01399g.
6
Effective anomerisation of 2'-deoxyadenosine derivatives during disaccharide nucleoside synthesis.
Nucleosides Nucleotides Nucleic Acids. 2004;23(12):1849-64. doi: 10.1081/NCN-200040627.
7
Facile preparation of the oxetane-nucleosides.
Org Biomol Chem. 2005 Dec 21;3(24):4362-72. doi: 10.1039/b511406c. Epub 2005 Nov 7.
9
Strategies for the Synthesis of Fluorinated Nucleosides, Nucleotides and Oligonucleotides.
Chem Rec. 2022 Sep;22(9):e202200066. doi: 10.1002/tcr.202200066. Epub 2022 May 31.
10
Optimized Biocatalytic Synthesis of 2-Selenopyrimidine Nucleosides by Transglycosylation*.
Chembiochem. 2021 Jun 2;22(11):2002-2009. doi: 10.1002/cbic.202100067. Epub 2021 Mar 31.

引用本文的文献

1
The XNA alphabet.
Nucleic Acids Res. 2025 Jul 8;53(13). doi: 10.1093/nar/gkaf635.
3
Comparative genomics of the highly halophilic Haloferacaceae.
Sci Rep. 2024 Nov 6;14(1):27025. doi: 10.1038/s41598-024-78438-8.
4
Prebiotic N-(2-Aminoethyl)-Glycine (AEG)-Assisted Synthesis of Proto-RNA?
J Mol Evol. 2024 Aug;92(4):449-466. doi: 10.1007/s00239-024-10185-w. Epub 2024 Jul 25.
7
Prebiotic synthesis and triphosphorylation of 3'-amino-TNA nucleosides.
Nat Chem. 2022 Jul;14(7):766-774. doi: 10.1038/s41557-022-00982-5. Epub 2022 Jul 1.
8
Novel 1'-homo--2'-deoxy-α-nucleosides: synthesis, characterization and biological activity.
RSC Adv. 2020;10(27):15815-15824. doi: 10.1039/D0RA03254A. Epub 2020 Apr 21.
9
Anomeric and Enantiomeric 2'-Deoxycytidines: Base Pair Stability in the Absence and Presence of Silver Ions.
Chemistry. 2021 Jul 21;27(41):10574-10577. doi: 10.1002/chem.202101253. Epub 2021 Jun 10.
10
The α-D-anomer of 2'-deoxycytidine: crystal structure, nucleoside conformation and Hirshfeld surface analysis.
Acta Crystallogr C Struct Chem. 2021 May 1;77(Pt 5):202-208. doi: 10.1107/S2053229621003430. Epub 2021 Apr 9.

本文引用的文献

1
Guanosine-Derived Supramolecular Hydrogels: Recent Developments and Future Opportunities.
ACS Omega. 2018 Feb 22;3(2):2230-2241. doi: 10.1021/acsomega.7b02039. eCollection 2018 Feb 28.
4
Replicative Bypass Studies of α-Anomeric Lesions of 2'-Deoxyribonucleosides in Vitro.
Chem Res Toxicol. 2017 May 15;30(5):1127-1133. doi: 10.1021/acs.chemrestox.6b00439. Epub 2017 Apr 14.
6
Synthesis and Evaluation of 2'-Deoxy-2'-Spirodiflurocyclopropyl Nucleoside Analogs.
Nucleosides Nucleotides Nucleic Acids. 2016 Sep;35(9):479-94. doi: 10.1080/15257770.2016.1202965. Epub 2016 Aug 11.
7
In vivo detection and replication studies of α-anomeric lesions of 2'-deoxyribonucleosides.
Nucleic Acids Res. 2015 Sep 30;43(17):8314-24. doi: 10.1093/nar/gkv725. Epub 2015 Jul 21.
8
Synthesis and evaluation of α-thymidine analogues as novel antimalarials.
J Med Chem. 2012 Dec 27;55(24):10948-57. doi: 10.1021/jm301328h. Epub 2012 Dec 14.
9
DNA sequence context conceals α-anomeric lesions.
J Mol Biol. 2012 Feb 24;416(3):425-37. doi: 10.1016/j.jmb.2011.12.051. Epub 2011 Dec 29.
10
Potential application of thymidylate kinase in nucleoside analogue activation in Plasmodium falciparum.
Bioorg Med Chem. 2010 Oct 15;18(20):7302-9. doi: 10.1016/j.bmc.2010.07.006. Epub 2010 Aug 6.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验