Suppr超能文献

含2-硫代嘧啶残基的寡脱氧核苷酸的合成——一种新的保护策略。

Synthesis of oligodeoxynucleotides containing 2-thiopyrimidine residues--a new protection scheme.

作者信息

Kuimelis R G, Nambiar K P

机构信息

Department of Chemistry, University of California, Davis 95616.

出版信息

Nucleic Acids Res. 1994 Apr 25;22(8):1429-36. doi: 10.1093/nar/22.8.1429.

DOI:10.1093/nar/22.8.1429
PMID:8190635
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC308001/
Abstract

A method is described for the incorporation of 2'-deoxy-2-thiouridine (dS2U) and 2'-deoxy-2-thiothymidine (dS2T) into oligodeoxynucleotides at predetermined positions. This requires N3 or O4-acylation of dS2U and dS2T with toluoyl chloride. These base-protected thiopyrimidines are completely stable toward the aqueous iodine oxidation reagent used in the phosphoramidite DNA synthesis method. The toluoyl protecting group is removed during the standard post-synthetic ammonia treatment. This novel protection strategy allows dS2U and dS2T to be efficiently incorporated into oligodeoxynucleotides at predetermined sites without the usual problem of desulfurization and decomposition. Several 14-mers containing the Eco-RI recognition site (dGGCGGAAXXCCGCC and dGGCGGAAXXCGCGG, where X represents dT, dS2U or dS2T) have been synthesized and characterized by base composition, thermal denaturation, CD spectroscopy and endonuclease substrate activity.

摘要

描述了一种将2'-脱氧-2-硫代尿苷（dS2U）和2'-脱氧-2-硫代胸苷（dS2T）掺入到寡脱氧核苷酸预定位置的方法。这需要用甲苯甲酰氯对dS2U和dS2T进行N3或O4酰化。这些碱基保护的硫代嘧啶对亚磷酰胺DNA合成方法中使用的水性碘氧化试剂完全稳定。在标准的合成后氨处理过程中，甲苯甲酰保护基被除去。这种新颖的保护策略允许dS2U和dS2T在预定位点有效地掺入寡脱氧核苷酸中，而没有通常的脱硫和分解问题。已经合成了几种含有Eco-RI识别位点的14聚体（dGGCGGAAXXCCGCC和dGGCGGAAXXCGCGG，其中X代表dT、dS2U或dS2T），并通过碱基组成、热变性、圆二色光谱和核酸内切酶底物活性进行了表征。

相似文献

1
Synthesis of oligodeoxynucleotides containing 2-thiopyrimidine residues--a new protection scheme.含2-硫代嘧啶残基的寡脱氧核苷酸的合成——一种新的保护策略。
Nucleic Acids Res. 1994 Apr 25;22(8):1429-36. doi: 10.1093/nar/22.8.1429.
2
Synthesis and properties of oligodeoxynucleotides containing the analogue 2'-deoxy-4'-thiothymidine.含类似物2'-脱氧-4'-硫代胸苷的寡脱氧核苷酸的合成与性质
Nucleic Acids Res. 1993 Jul 25;21(15):3485-91. doi: 10.1093/nar/21.15.3485.
3
Synthesis and selective cleavage of an oligodeoxynucleotide containing a bridged internucleotide 5'-phosphorothioate linkage.
Nucleic Acids Res. 1991 Apr 11;19(7):1437-41. doi: 10.1093/nar/19.7.1437.
4
Synthesis and properties of oligonucleotides containing 4-thiothymidine, 5-methyl-2-pyrimidinone-1-beta-D(2'-deoxyriboside) and 2-thiothymidine.含4-硫代胸腺嘧啶、5-甲基-2-嘧啶酮-1-β-D（2'-脱氧核糖核苷）和2-硫代胸腺嘧啶的寡核苷酸的合成与性质
Nucleic Acids Res. 1989 Jul 11;17(13):4957-74. doi: 10.1093/nar/17.13.4957.
5
5-Fluoro-4-thiouridine phosphoramidite: new synthon for introducing photoaffinity label into oligodeoxynucleotides.5-氟-4-硫代尿嘧啶核苷亚磷酰胺：将光亲和性标记引入寡脱氧核苷酸的新前体。
Bioorg Med Chem. 2011 Oct 15;19(20):6098-106. doi: 10.1016/j.bmc.2011.08.035. Epub 2011 Aug 22.
6
Oligodeoxynucleotides containing 4-thiothymidine and 6-thiodeoxyguanosine as affinity labels for the Eco RV restriction endonuclease and modification methylase.含有4-硫代胸腺嘧啶核苷和6-硫代脱氧鸟苷的寡脱氧核苷酸作为Eco RV限制性内切酶和修饰甲基化酶的亲和标记。
Nucleic Acids Res. 1992 Mar 25;20(6):1209-14. doi: 10.1093/nar/20.6.1209.
7
The synthesis of 2-pyrimidinone nucleosides and their incorporation into oligodeoxynucleotides.2-嘧啶酮核苷的合成及其掺入寡脱氧核苷酸中。
Nucleic Acids Res. 1989 Mar 25;17(6):2261-81. doi: 10.1093/nar/17.6.2261.
8
Oligodeoxynucleotides having a loop consisting of 3'-deoxy-4'-C-(2-hydroxyethyl)thymidines form stable hairpins.具有由3'-脱氧-4'-C-(2-羟乙基)胸苷组成的环的寡脱氧核苷酸形成稳定的发夹结构。
Biochemistry. 2004 Jul 13;43(27):8690-9. doi: 10.1021/bi0496283.
9
Incorporation of (R)- and (S)-3',4'-seco-thymidine into oligodeoxynucleotides: hybridization properties and enzymatic stability.将（R）-和（S）-3'，4'-裂胸腺嘧啶核苷掺入寡脱氧核苷酸：杂交特性和酶稳定性
Nucleic Acids Res. 1994 Mar 11;22(5):703-10. doi: 10.1093/nar/22.5.703.
10
Triplex forming ability of oligonucleotides containing 2'-O-methyl-2-thiouridine or 2-thiothymidine.含有2'-O-甲基-2-硫代尿苷或2-硫代胸苷的寡核苷酸的三链体形成能力。
Bioorg Med Chem Lett. 2006 Jun 15;16(12):3334-6. doi: 10.1016/j.bmcl.2006.02.019. Epub 2006 May 2.

引用本文的文献

1
2-Thiouracil deprived of thiocarbonyl function preferentially base pairs with guanine rather than adenine in RNA and DNA duplexes.在RNA和DNA双链体中，失去硫羰基功能的2-硫尿嘧啶优先与鸟嘌呤而非腺嘌呤形成碱基对。
Nucleic Acids Res. 2015 Mar 11;43(5):2499-512. doi: 10.1093/nar/gkv109. Epub 2015 Feb 17.
2
Pseudo-complementary PNA actuators as reversible switches in dynamic DNA nanotechnology.作为动态 DNA 纳米技术中可逆开关的伪互补 PNA 驱动器。
Nucleic Acids Res. 2013 Apr;41(8):4729-39. doi: 10.1093/nar/gkt121. Epub 2013 Feb 26.
3
tRNA structural and functional changes induced by oxidative stress.氧化应激诱导的 tRNA 结构和功能变化。
Cell Mol Life Sci. 2011 Dec;68(24):4023-32. doi: 10.1007/s00018-011-0773-8. Epub 2011 Aug 11.
4
Enhanced base pairing and replication efficiency of thiothymidines, expanded-size variants of thymidine.硫代胸苷（胸苷的扩展大小变体）的碱基配对增强及复制效率提高。
J Am Chem Soc. 2006 Jan 18;128(2):396-7. doi: 10.1021/ja0562447.
5
Covalent cross-linking of duplex DNA using 4-thio-2'-deoxyuridine as a readily modifiable platform for introduction of reactive functionality into oligonucleotides.使用4-硫代-2'-脱氧尿苷作为易于修饰的平台，将反应性功能引入寡核苷酸中，实现双链DNA的共价交联。
Nucleic Acids Res. 1997 Dec 1;25(23):4771-7. doi: 10.1093/nar/25.23.4771.

本文引用的文献

1
Importance of specific guanosine N7-nitrogens and purine amino groups for efficient cleavage by a hammerhead ribozyme.特定鸟苷N7氮原子和嘌呤氨基对于锤头状核酶高效切割的重要性。
Biochemistry. 1993 Oct 12;32(40):10629-37. doi: 10.1021/bi00091a013.
2
Facilitated distortion of the DNA site enhances EcoRI endonuclease-DNA recognition.DNA位点的易化扭曲增强了EcoRI核酸内切酶与DNA的识别。
Proc Natl Acad Sci U S A. 1993 Aug 15;90(16):7548-52. doi: 10.1073/pnas.90.16.7548.
3
The synthesis of oligoribonucleotides containing O6-methylguanosine: the role of conserved guanosine residues in hammerhead ribozyme cleavage.含O6-甲基鸟苷的寡核糖核苷酸的合成：锤头状核酶切割中保守鸟苷残基的作用
Nucleic Acids Res. 1993 Sep 25;21(19):4444-50. doi: 10.1093/nar/21.19.4444.
4
Assignment of the non-exchangeable proton resonances of d(C-G-C-G-A-A-T-T-C-G-C-G) using two-dimensional nuclear magnetic resonance methods.使用二维核磁共振方法对d（C-G-C-G-A-A-T-T-C-G-C-G）的非交换质子共振进行归属
J Mol Biol. 1983 Dec 15;171(3):319-36. doi: 10.1016/0022-2836(83)90096-7.
5
[The chemical synthesis of 2,4-dithiothymine nucleosides].
Chem Ber. 1970;103(5):1307-11. doi: 10.1002/cber.19701030502.
6
Circular dichroism and its empirical application to biopolymers.圆二色性及其在生物聚合物中的实证应用。
Methods Biochem Anal. 1985;31:61-163. doi: 10.1002/9780470110522.ch2.
7
Calculating thermodynamic data for transitions of any molecularity from equilibrium melting curves.根据平衡熔化曲线计算任何分子数转变的热力学数据。
Biopolymers. 1987 Sep;26(9):1601-20. doi: 10.1002/bip.360260911.
8
Stacking interactions of tryptophan residues and nucleotide bases in complexes formed between Escherichia coli single-stranded DNA binding protein and heavy atom-modified poly(uridylic) acid. A study by optically detected magnetic resonance spectroscopy.大肠杆菌单链DNA结合蛋白与重原子修饰的聚（尿苷酸）酸形成的复合物中色氨酸残基与核苷酸碱基的堆积相互作用。光检测磁共振光谱研究。
J Biol Chem. 1987 Feb 5;262(4):1725-33.
9
The effects of base analogue substitutions on the methylation by the EcoRI modification methylase of octadeoxyribonucleotides containing modified EcoRI recognition sequences.碱基类似物取代对含有修饰的EcoRI识别序列的十八聚脱氧核糖核苷酸经EcoRI甲基化酶甲基化的影响。
J Biol Chem. 1986 Jun 5;261(16):7279-86.
10
The effects of base analogue substitutions on the cleavage by the EcoRI restriction endonuclease of octadeoxyribonucleotides containing modified EcoRI recognition sequences.碱基类似物取代对含有修饰的EcoRI识别序列的十八聚脱氧核糖核苷酸经EcoRI限制性内切核酸酶切割的影响。
J Biol Chem. 1986 Jun 5;261(16):7270-8.

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