适用于2'-O-烯丙基寡核糖核苷酸组装的合成子的新合成路线。
New synthetic routes to synthons suitable for 2'-O-allyloligoribonucleotide assembly.
作者信息
Sproat B S, Iribarren A M, Garcia R G, Beijer B
机构信息
European Molecular Biology Laboratory, Heidelberg, FRG.
出版信息
Nucleic Acids Res. 1991 Feb 25;19(4):733-8. doi: 10.1093/nar/19.4.733.
Abstract
New synthetic routes have been devised for the high yield preparation of protected 2'-O-allylribonucleoside-3'-O-phosphoramidites, exemplified by the ribonucleosides guanosine and 2,6-diaminopurine riboside (2-aminoadenosine). Key features are the use of versatile intermediates and an easy allylation step. The development of a novel synthon based on 2'-O-allyl-2,6-diaminopurine riboside enables short 2'-O-allyl-oligoribonucleotide probes to be synthesized with adenine replaced by 2-aminoadenine. Thus very stable hybrids with complementary RNA target sequences can be formed due to the formation of the three hydrogen bond 2-amino A.U base pairs.
摘要
已设计出用于高产率制备受保护的2'-O-烯丙基核糖核苷-3'-O-亚磷酰胺的新合成路线，鸟苷和2,6-二氨基嘌呤核糖核苷（2-氨基腺苷）核糖核苷即为示例。关键特征是使用通用中间体和简便的烯丙基化步骤。基于2'-O-烯丙基-2,6-二氨基嘌呤核糖核苷的新型合成子的开发，使得能够合成短的2'-O-烯丙基寡核糖核苷酸探针，其中腺嘌呤被2-氨基腺嘌呤取代。因此，由于形成了三个氢键的2-氨基A.U碱基对，可与互补RNA靶序列形成非常稳定的杂交体。
相似文献
1
New synthetic routes to synthons suitable for 2'-O-allyloligoribonucleotide assembly.适用于2'-O-烯丙基寡核糖核苷酸组装的合成子的新合成路线。
Nucleic Acids Res. 1991 Feb 25;19(4):733-8. doi: 10.1093/nar/19.4.733.
2
New synthetic routes to protected purine 2'-O-methylriboside-3'-O-phosphoramidites using a novel alkylation procedure.使用一种新型烷基化方法合成受保护嘌呤2'-O-甲基核糖核苷-3'-O-亚磷酰胺的新路线。
Nucleic Acids Res. 1990 Jan 11;18(1):41-9. doi: 10.1093/nar/18.1.41.
3
2'-O-alkyloligoribonucleotides, synthesis and applications in molecular biology.2'-O-烷基寡核糖核苷酸的合成及其在分子生物学中的应用。
Nucleic Acids Symp Ser. 1991(24):59-62.
4
A chemical synthesis of LNA-2,6-diaminopurine riboside, and the influence of 2'-O-methyl-2,6-diaminopurine and LNA-2,6-diaminopurine ribosides on the thermodynamic properties of 2'-O-methyl RNA/RNA heteroduplexes.LNA - 2,6 - 二氨基嘌呤核苷的化学合成以及2'-O - 甲基 - 2,6 - 二氨基嘌呤和LNA - 2,6 - 二氨基嘌呤核苷对2'-O - 甲基RNA/RNA异源双链体热力学性质的影响。
Nucleic Acids Res. 2007;35(12):4055-63. doi: 10.1093/nar/gkm421. Epub 2007 Jun 12.
5
Chemical synthesis of branched RNA.分支RNA的化学合成
Nucleic Acids Res. 1986 Jun 25;14(12):4751-64. doi: 10.1093/nar/14.12.4751.
6
Chemical synthesis of RNA sequences with 2'-O-[(triisopropylsilyl)oxy]methyl-protected ribonucleoside phosphoramidites.使用2'-O-[(三异丙基甲硅烷基)氧基]甲基保护的核糖核苷亚磷酰胺进行RNA序列的化学合成。
Curr Protoc Nucleic Acid Chem. 2002 Feb;Chapter 3:Unit 3.8. doi: 10.1002/0471142700.nc0308s07.
7
8
Synthesis of 2'-O-[2-(N-methylcarbamoyl)ethyl]ribonucleosides using oxa-Michael reaction and chemical and biological properties of oligonucleotide derivatives incorporating these modified ribonucleosides.利用氧杂-Michael 反应合成 2'-O-[2-(N-甲基氨基甲酰基)乙基]核苷，并研究了这些修饰核苷的寡核苷酸衍生物的化学和生物学性质。
J Org Chem. 2011 May 6;76(9):3042-53. doi: 10.1021/jo101963z. Epub 2011 Mar 23.
9
Advances in the chemical synthesis and purification of RNA.RNA化学合成与纯化的进展
Nucleic Acids Symp Ser. 1995(33):123-5.
10
Synthesis of isotopically labeled D-[1'-13C]ribonucleoside phosphoramidites.同位素标记的 D-[1'-¹³C]核糖核苷亚磷酰胺的合成。
Carbohydr Res. 2001 Mar 9;331(1):83-90. doi: 10.1016/s0008-6215(00)00327-x.
引用本文的文献
1
A Chemical Approach to Introduce 2,6-Diaminopurine and 2-Aminoadenine Conjugates into Oligonucleotides without Need for Protecting Groups.一种无需保护基团即可将 2,6-二氨基嘌呤和 2-氨基腺嘌呤缀合到寡核苷酸中的化学方法。
Org Lett. 2022 Aug 26;24(33):6111-6116. doi: 10.1021/acs.orglett.2c01848. Epub 2022 Aug 16.
2
The 2-Amino Group of 8-Aza-7-deaza-7-bromopurine-2,6-diamine and Purine-2,6-diamine as Stabilizer for the Adenine-Thymine Base Pair in Heterochiral DNA with Strands in Anomeric Configuration.8-氮杂-7-去氮-7-溴鸟嘌呤-2,6-二氨基和嘌呤-2,6-二氨基 2-氨基作为非手性 DNA 中糖苷构型链上腺嘌呤-胸腺嘧啶碱基对的稳定剂。
Chemistry. 2021 Jan 26;27(6):2093-2103. doi: 10.1002/chem.202004221. Epub 2020 Dec 21.
3
Combined Approaches to Site-Specific Modification of RNA.RNA位点特异性修饰的联合方法
ACS Chem Biol. 2008 Jan 18;3(1):30-37. doi: 10.1021/cb7002225. Epub 2008 Jan 5.
4
Pyrazolo[3,4-d]pyrimidine nucleic acids: adjustment of dA-dT to dG-dC base pair stability.吡唑并[3,4-d]嘧啶核酸：dA-dT到dG-dC碱基对稳定性的调整。
Nucleic Acids Res. 2001 May 15;29(10):2069-78. doi: 10.1093/nar/29.10.2069.
5
Formation of a covalent complex between methylguanine methyltransferase and DNA via disulfide bond formation between the active site cysteine and a thiol-containing analog of guanine.通过活性位点半胱氨酸与含硫醇的鸟嘌呤类似物之间形成二硫键，使甲基鸟嘌呤甲基转移酶与DNA形成共价复合物。
Nucleic Acids Res. 1997 May 1;25(9):1795-801. doi: 10.1093/nar/25.9.1795.
6
Synthesis and hybridization properties of oligonucleotides containing 2'-O-modified ribonucleotides.含2'-O-修饰核糖核苷酸的寡核苷酸的合成与杂交特性
Nucleic Acids Res. 1993 Sep 25;21(19):4499-505. doi: 10.1093/nar/21.19.4499.
7
The role of the 5' untranslated region of eukaryotic messenger RNAs in translation and its investigation using antisense technologies.真核生物信使核糖核酸5'非翻译区在翻译中的作用及其利用反义技术进行的研究。
Prog Nucleic Acid Res Mol Biol. 1994;48:181-238. doi: 10.1016/s0079-6603(08)60856-9.
8
Solid phase synthesis of 5'-diphosphorylated oligoribonucleotides and their conversion to capped m7Gppp-oligoribonucleotides for use as primers for influenza A virus RNA polymerase in vitro.5'-二磷酸化寡核糖核苷酸的固相合成及其转化为帽化的m7Gppp-寡核糖核苷酸，用作甲型流感病毒RNA聚合酶体外引物。
Nucleic Acids Res. 1995 Jul 25;23(14):2641-7. doi: 10.1093/nar/23.14.2641.
9
A simple procedure for the preparation of protected 2'-O-methyl or 2'-O-ethyl ribonucleoside-3'-O-phosphoramidites.一种制备2'-O-甲基或2'-O-乙基核糖核苷-3'-O-亚磷酰胺酯的简单方法。
Nucleic Acids Res. 1991 Nov 11;19(21):5965-71. doi: 10.1093/nar/19.21.5965.
10
In vivo detection of snRNP-rich organelles in the nuclei of mammalian cells.哺乳动物细胞核中富含小核核糖核蛋白（snRNP）的细胞器的体内检测。
EMBO J. 1991 Jul;10(7):1863-73. doi: 10.1002/j.1460-2075.1991.tb07712.x.
本文引用的文献
1
Polymer support oligonucleotide synthesis XVIII: use of beta-cyanoethyl-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product.聚合物载体寡核苷酸合成 XVIII：脱氧核苷的β-氰基乙基-N，N-二烷基氨基-/N-吗啉代亚磷酰胺用于 DNA 片段合成，简化最终产物的脱保护和分离
Nucleic Acids Res. 1984 Jun 11;12(11):4539-57. doi: 10.1093/nar/12.11.4539.
2
2NH2A X T helices in the ribo- and deoxypolynucleotide series. Structural and energetic consequences of 2NH2A substitution.核糖核苷酸和脱氧多核苷酸系列中的2NH2A X T螺旋。2NH2A取代的结构和能量后果。
Biochemistry. 1984 Dec 18;23(26):6723-32. doi: 10.1021/bi00321a068.
3
Synthesis of 2'-O-methyluridine, 2'-O-methylcytidine and their relating compounds.2'-O-甲基尿苷、2'-O-甲基胞苷及其相关化合物的合成。
Chem Pharm Bull (Tokyo). 1965 Nov;13(11):1273-8. doi: 10.1248/cpb.13.1273.
4
The interaction of actinomycin with DNA: requirement for the 2-amino group of purines.放线菌素与DNA的相互作用：嘌呤2-氨基基团的必要性。
Proc Natl Acad Sci U S A. 1967 Apr;57(4):1036-42. doi: 10.1073/pnas.57.4.1036.
5
The final deprotection step in oligonucleotide synthesis is reduced to a mild and rapid ammonia treatment by using labile base-protecting groups.通过使用不稳定的碱基保护基团，寡核苷酸合成中的最终脱保护步骤简化为温和且快速的氨处理。
Nucleic Acids Res. 1987 Jan 26;15(2):397-416. doi: 10.1093/nar/15.2.397.
6
Synthesis of O2'-methyluridine, O2'-methylcytidine, N4,O2'-dimethylcytidine and N4,N4,O2'-trimethylcytidine from a common intermediate.由一个共同中间体合成2'-O-甲基尿苷、2'-O-甲基胞苷、N4,2'-O-二甲基胞苷和N4,N4,2'-O-三甲基胞苷。
Acta Chem Scand B. 1986 Nov;40(10):826-30. doi: 10.3891/acta.chem.scand.40b-0826.
7
Prevention of chain cleavage in the chemical synthesis of 2'-silylated oligoribonucleotides.2'-硅烷化寡核糖核苷酸化学合成中链裂解的预防
Nucleic Acids Res. 1989 May 11;17(9):3501-17. doi: 10.1093/nar/17.9.3501.
8
Highly efficient chemical synthesis of 2'-O-methyloligoribonucleotides and tetrabiotinylated derivatives; novel probes that are resistant to degradation by RNA or DNA specific nucleases.2'-O-甲基寡核糖核苷酸及其四生物素化衍生物的高效化学合成；对RNA或DNA特异性核酸酶降解具有抗性的新型探针。
Nucleic Acids Res. 1989 May 11;17(9):3373-86. doi: 10.1093/nar/17.9.3373.
9
New synthetic routes to protected purine 2'-O-methylriboside-3'-O-phosphoramidites using a novel alkylation procedure.使用一种新型烷基化方法合成受保护嘌呤2'-O-甲基核糖核苷-3'-O-亚磷酰胺的新路线。
Nucleic Acids Res. 1990 Jan 11;18(1):41-9. doi: 10.1093/nar/18.1.41.
10
2'-O-alkyl oligoribonucleotides as antisense probes.2'-O-烷基寡核糖核苷酸作为反义探针。
Proc Natl Acad Sci U S A. 1990 Oct;87(19):7747-51. doi: 10.1073/pnas.87.19.7747.
Zotero 插件