使用9-芴甲氧羰基（Fmoc）对5'-羟基进行保护的寡核糖核苷酸的固相合成。
Solid-phase synthesis of oligoribonucleotides using 9-fluorenylmethoxycarbonyl (Fmoc) for 5'-hydroxyl protection.
作者信息
Lehmann C, Xu Y Z, Christodoulou C, Tan Z K, Gait M J
机构信息
Medical Research Council, Laboratory of Molecular Biology, Cambridge, UK.
出版信息
Nucleic Acids Res. 1989 Apr 11;17(7):2379-90. doi: 10.1093/nar/17.7.2379.
Abstract
Efficient solid-phase synthesis of a series of oligoribonucleotides of up to 20 residues is described that utilises the 9-fluorenylmethoxycarbonyl group (Fmoc) for 5'-protection and 4-methoxytetrahydropyran-4-yl (Mthp) for 2'-protection of ribonucleotide monomers and a phosphoramidite coupling procedure. The Fmoc group is removed after each coupling step by treatment with 0.1M DBU in acetonitrile. Oligoribonucleotides are isolated in 2'-protected form in good yield and shown to be readily and efficiently deprotected by mild acidic treatment.
摘要
本文描述了一系列长达20个残基的寡核糖核苷酸的高效固相合成方法，该方法利用9-芴甲氧羰基（Fmoc）对核糖核苷酸单体进行5'-保护，4-甲氧基四氢吡喃-4-基（Mthp）进行2'-保护，并采用亚磷酰胺偶联程序。在每个偶联步骤后，通过用0.1M二氮杂双环十一碳烯（DBU）的乙腈溶液处理来除去Fmoc基团。寡核糖核苷酸以2'-保护形式高产率分离得到，并显示通过温和的酸性处理可容易且有效地脱保护。
相似文献
1
Solid-phase synthesis of oligoribonucleotides using 9-fluorenylmethoxycarbonyl (Fmoc) for 5'-hydroxyl protection.使用9-芴甲氧羰基（Fmoc）对5'-羟基进行保护的寡核糖核苷酸的固相合成。
Nucleic Acids Res. 1989 Apr 11;17(7):2379-90. doi: 10.1093/nar/17.7.2379.
2
Solid-phase synthesis of oligoribonucleotides.
Nucleic Acids Symp Ser. 1989(21):39-40.
3
The acetal levulinyl ester (ALE) group for the 2'-hydroxyl protection of ribonucleosides and the synthesis of oligoribonucleotides.用于核糖核苷2'-羟基保护及寡核糖核苷酸合成的乙酰丙酰基酯（ALE）基团。
Nucleic Acids Symp Ser (Oxf). 2008(52):35-6. doi: 10.1093/nass/nrn018.
4
Synthesis of oligoribonucleotides using the 2-nitrobenzyloxymethyl group for 2'-hydroxyl protection.使用2-硝基苄氧基甲基基团进行2'-羟基保护合成寡核糖核苷酸。
Curr Protoc Nucleic Acid Chem. 2001 May;Chapter 3:Unit 3.7. doi: 10.1002/0471142700.nc0307s03.
5
Synthesis of RNA oligomer using 9-fluorenylmethoxycarbonyl (Fmoc) group for 5'-hydroxyl protection.
Nucleic Acids Symp Ser. 1988(19):13-6.
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
Preparation of 2'-O-[(Triisopropylsilyl)oxy]methyl-protected ribonucleosides.2'-O-[(三异丙基甲硅烷基)氧基]甲基保护的核糖核苷的制备。
Curr Protoc Nucleic Acid Chem. 2002 Feb;Chapter 2:Unit 2.9. doi: 10.1002/0471142700.nc0209s07.
8
Synthesis of 5'-Thio-3'-O-ribonucleoside Phosphoramidites.5′-硫代-3′-O-核糖核苷亚磷酰胺的合成。
J Org Chem. 2017 Dec 1;82(23):12003-12013. doi: 10.1021/acs.joc.7b01484. Epub 2017 Oct 31.
9
A base-labile protecting group (fluorenylmethoxycarbonyl) for the 5'-hydroxy function of nucleosides.用于核苷5'-羟基官能团的碱不稳定保护基团（芴甲氧羰基）。
Curr Protoc Nucleic Acid Chem. 2001 May;Chapter 2:Unit 2.4. doi: 10.1002/0471142700.nc0204s00.
10
The 4-(N-dichloroacetyl-N-methylamino)benzyloxymethyl group for 2'-hydroxyl protection of ribonucleosides in the solid-phase synthesis of oligoribonucleotides.用于寡核糖核苷酸固相合成中核糖核苷2'-羟基保护的4-(N-二氯乙酰基-N-甲基氨基)苄氧甲基基团。
J Org Chem. 2008 Apr 4;73(7):2774-83. doi: 10.1021/jo702717g. Epub 2008 Mar 8.
引用本文的文献
1
Encapsulation of a novel peptide derived from histatin-1 in liposomes against initial enamel caries in vitro and in vivo.新型组蛋白衍生肽包封于脂质体中，用于体外和体内抗初始釉质龋。
Clin Oral Investig. 2023 Dec 26;28(1):35. doi: 10.1007/s00784-023-05465-6.
2
Synthetic approach to stop-codon scanning mutagenesis.合成方法实现终止密码子扫描突变。
J Am Chem Soc. 2011 Apr 27;133(16):6177-86. doi: 10.1021/ja106894g. Epub 2011 Mar 31.
3
Combinatorial codon-based amino acid substitutions.基于密码子组合的氨基酸替换
Nucleic Acids Res. 2004 Nov 10;32(20):e158. doi: 10.1093/nar/gnh156.
4
Novel ceftazidime-resistance beta-lactamases generated by a codon-based mutagenesis method and selection.通过基于密码子的诱变方法和筛选产生的新型耐头孢他啶β-内酰胺酶。
Nucleic Acids Res. 2002 Aug 15;30(16):e84. doi: 10.1093/nar/gnf083.
5
Orthogonal combinatorial mutagenesis: a codon-level combinatorial mutagenesis method useful for low multiplicity and amino acid-scanning protocols.正交组合诱变：一种适用于低多样性和氨基酸扫描方案的密码子水平组合诱变方法。
Nucleic Acids Res. 2001 Feb 1;29(3):E9. doi: 10.1093/nar/29.3.e9.
6
Synthesis and radioiodination of a stannyl oligodeoxyribonucleotide.一种甲锡烷基寡脱氧核糖核苷酸的合成与放射性碘化
Nucleic Acids Res. 1997 Jul 15;25(14):2897-901. doi: 10.1093/nar/25.14.2897.
7
Base-boronated dinucleotides: synthesis and effect of N7-cyanoborane substitution on the base protons.碱基硼化的二核苷酸：N7-氰基硼烷取代对碱基质子的合成及影响。
Nucleic Acids Res. 1996 Jun 1;24(11):2150-7. doi: 10.1093/nar/24.11.2150.
8
Generation and screening of an oligonucleotide-encoded synthetic peptide library.寡核苷酸编码合成肽库的生成与筛选
Proc Natl Acad Sci U S A. 1993 Nov 15;90(22):10700-4. doi: 10.1073/pnas.90.22.10700.
9
Chemical synthesis of the 24 RNA fragments corresponding to hop stunt viroid.对应啤酒花矮化类病毒的24个RNA片段的化学合成
Nucleic Acids Res. 1989 Oct 25;17(20):8135-47. doi: 10.1093/nar/17.20.8135.
10
Synthesis and applications of oligoribonucleotides with selected 2'-O-methylation using the 2'-O-[1-(2-fluorophenyl)-4-methoxypiperidin-4-yl] protecting group.使用2'-O-[1-(2-氟苯基)-4-甲氧基哌啶-4-基]保护基团合成及应用具有特定2'-O-甲基化的寡核糖核苷酸
Nucleic Acids Res. 1990 Sep 11;18(17):5143-51. doi: 10.1093/nar/18.17.5143.
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
Action of acid on oligoribonucleotide phosphotriester intermediates. Effect of released vicinal hydroxy functions.酸对寡核糖核苷酸磷酸三酯中间体的作用。释放的邻位羟基官能团的影响。
Nucleic Acids Res. 1985 Jul 25;13(14):5215-31. doi: 10.1093/nar/13.14.5215.
3
Solid phase synthesis of oligoribonucleotides using o-nitrobenzyl protection of 2'-hydroxyl via a phosphite triester approach.通过亚磷酸三酯法利用邻硝基苄基对2'-羟基进行保护的寡核糖核苷酸的固相合成。
Nucleic Acids Res. 1986 Aug 11;14(15):6265-79. doi: 10.1093/nar/14.15.6265.
4
Solid phase synthesis of oligoribonucleotides using the o-nitrobenzyl group for 2'-hydroxyl protection and H-phosphonate chemistry.使用邻硝基苄基进行2'-羟基保护和H-膦酸酯化学法固相合成寡核糖核苷酸。
Nucleic Acids Res. 1987 Sep 25;15(18):7235-48. doi: 10.1093/nar/15.18.7235.
5
Total chemical synthesis of a 77-nucleotide-long RNA sequence having methionine-acceptance activity.具有甲硫氨酸接受活性的77个核苷酸长的RNA序列的全化学合成。
Proc Natl Acad Sci U S A. 1988 Aug;85(16):5764-8. doi: 10.1073/pnas.85.16.5764.
6
5'-Levulinyl and 2'-tetrahydrofuranyl protection for the synthesis of oligoribonucleotides by the phosphoramidite approach.用于通过亚磷酰胺法合成寡核糖核苷酸的5'-乙酰基和2'-四氢呋喃基保护。
Nucleic Acids Res. 1988 Oct 25;16(20):9443-56. doi: 10.1093/nar/16.20.9443.
7
Studies on the t-butyldimethylsilyl group as 2'-O-protection in oligoribonucleotide synthesis via the H-phosphonate approach.通过H-膦酸酯法进行寡核糖核苷酸合成中叔丁基二甲基硅烷基作为2'-O-保护基的研究。
Nucleic Acids Res. 1988 Oct 11;16(19):9285-98. doi: 10.1093/nar/16.19.9285.
8
Synthesis of RNA oligomer using 9-fluorenylmethoxycarbonyl (Fmoc) group for 5'-hydroxyl protection.
Nucleic Acids Symp Ser. 1988(19):13-6.
9
The synthesis of oligoribonucleotides. Part XI. Preparation of ribonucleoside 2'-acetal 3'-esters by selective deacylation.寡核糖核苷酸的合成。第十一章。通过选择性脱酰作用制备核糖核苷2'-缩醛3'-酯。
J Chem Soc Perkin 1. 1975(10):934-42. doi: 10.1039/p19750000934.
Zotero 插件