• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

寡聚-2-嘧啶酮-2'-脱氧核糖核苷酸和寡聚-2-嘧啶酮-2'-脱氧核苷甲基膦酸酯的固相合成

Solid-phase synthesis of oligo-2-pyrimidinone-2'-deoxyribonucleotides and oligo-2-pyrimidinone-2'-deoxyriboside methylphosphonates.

作者信息

Zhou Y, Ts'o P O

机构信息

Department of Biochemistry, School of Hygiene and Public Health, Johns Hopkins University, Baltimore, MD 21205, USA.

出版信息

Nucleic Acids Res. 1996 Jul 15;24(14):2652-9. doi: 10.1093/nar/24.14.2652.

DOI:10.1093/nar/24.14.2652
PMID:8758991
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC145996/
Abstract

A synthetic method was developed for the synthesis of oligodeoxyribonucleotides and oligodeoxyribonucleoside methylphosphonates comprised exclusively of the fluorescent 2-pyrimidinone base for the first time. The method utilized the solid-phase 2-cyanoethylphosphoramidite and methylphosphonamidite chemistry for internucleotide couplings and a baselabile oxalyl linkage to anchor the oligomers onto the CPG support. Cleavage of the oligomers from the support was effected by a short treatment of the support with 5% ammonium hydroxide in methanol at room temperature, without any degradation of the base-sensitive 2-pyrimidinone residues or the base-sensitive methylphosphonate backbone.

摘要

首次开发了一种合成方法,用于合成仅由荧光2-嘧啶酮碱基组成的寡脱氧核糖核苷酸和寡脱氧核糖核苷甲基膦酸酯。该方法利用固相2-氰基乙基亚磷酰胺和甲基膦酰胺化学进行核苷酸间偶联,并使用碱不稳定的草酰基连接将寡聚物锚定在CPG载体上。通过在室温下用5%氢氧化铵的甲醇溶液对载体进行短时间处理,可将寡聚物从载体上切割下来,而不会使对碱敏感的2-嘧啶酮残基或对碱敏感的甲基膦酸酯主链发生任何降解。

相似文献

1
Solid-phase synthesis of oligo-2-pyrimidinone-2'-deoxyribonucleotides and oligo-2-pyrimidinone-2'-deoxyriboside methylphosphonates.寡聚-2-嘧啶酮-2'-脱氧核糖核苷酸和寡聚-2-嘧啶酮-2'-脱氧核苷甲基膦酸酯的固相合成
Nucleic Acids Res. 1996 Jul 15;24(14):2652-9. doi: 10.1093/nar/24.14.2652.
2
Automated synthesis of oligodeoxyribonucleoside methylphosphonates having [N-(3-aminoprop-1-yl)-N-(2-hydroxyethyl)-2-aminoethyl] phosphate or methylphosphonic acid at the 3' end using a modified controlled pore glass support.使用改性的可控孔径玻璃载体自动合成在3'端具有[ N-(3-氨基丙-1-基)-N-(2-羟乙基)-2-氨基乙基]磷酸酯或甲基膦酸的寡脱氧核糖核苷甲基膦酸酯。
Bioconjug Chem. 1993 Sep-Oct;4(5):395-401. doi: 10.1021/bc00023a015.
3
Solid-phase syntheses of oligodeoxyribonucleoside methylphosphonates.寡脱氧核糖核苷甲基膦酸酯的固相合成
Biochemistry. 1986 Sep 9;25(18):5092-7. doi: 10.1021/bi00366a017.
4
Control of ribonucleic acid function by oligonucleoside methylphosphonates.寡核苷膦酸酯对核糖核酸功能的控制
Biochimie. 1985 Jul-Aug;67(7-8):769-76. doi: 10.1016/s0300-9084(85)80166-8.
5
Oxalyl-CPG: a labile support for synthesis of sensitive oligonucleotide derivatives.草酰基-CPG:用于合成敏感寡核苷酸衍生物的不稳定载体。
Nucleic Acids Res. 1991 Apr 11;19(7):1527-32. doi: 10.1093/nar/19.7.1527.
6
Use of EDTA derivatization to characterize interactions between oligodeoxyribonucleoside methylphosphonates and nucleic acids.使用乙二胺四乙酸(EDTA)衍生化来表征寡脱氧核糖核苷甲基膦酸酯与核酸之间的相互作用。
Biochemistry. 1989 Feb 7;28(3):1054-61. doi: 10.1021/bi00429a020.
7
Preparation of oligodeoxyribonucleoside methylphosphonates on a polystyrene support.在聚苯乙烯载体上制备寡脱氧核糖核苷甲基膦酸酯。
Nucleic Acids Res. 1983 Sep 24;11(18):6225-42. doi: 10.1093/nar/11.18.6225.
8
Comparative hybrid arrest by tandem antisense oligodeoxyribonucleotides or oligodeoxyribonucleoside methylphosphonates in a cell-free system.在无细胞系统中,串联反义寡脱氧核苷酸或寡脱氧核苷甲基膦酸酯的比较性杂交捕获
Nucleic Acids Res. 1988 Apr 25;16(8):3341-58. doi: 10.1093/nar/16.8.3341.
9
Characterization of sequence-specific oligodeoxyribonucleoside methylphosphonates and their interaction with rabbit globin mRNA.序列特异性寡脱氧核糖核苷甲基膦酸酯的表征及其与兔珠蛋白mRNA的相互作用。
Biochemistry. 1985 Jul 16;24(15):4041-6. doi: 10.1021/bi00336a036.
10
Interaction of psoralen-derivatized oligodeoxyribonucleoside methylphosphonates with single-stranded DNA.补骨脂素衍生的寡脱氧核糖核苷甲基膦酸酯与单链DNA的相互作用。
Biochemistry. 1988 May 3;27(9):3197-203. doi: 10.1021/bi00409a011.

引用本文的文献

1
Electronic and structural elements that regulate the excited-state dynamics in purine nucleobase derivatives.调节嘌呤核苷酸碱基衍生物激发态动力学的电子和结构元素。
J Am Chem Soc. 2015 Apr 8;137(13):4368-81. doi: 10.1021/ja512536c. Epub 2015 Mar 25.
2
Chemical mapping of cytosines enzymatically flipped out of the DNA helix.对从DNA螺旋中酶促翻转出来的胞嘧啶进行化学图谱分析。
Nucleic Acids Res. 2008 Jun;36(10):e57. doi: 10.1093/nar/gkn200. Epub 2008 May 1.
3
Post-synthetic and site-specific modification of endocyclic nitrogen atoms of purines in DNA and its potential for biological and structural studies.
Nucleic Acids Res. 2005 Mar 23;33(6):1767-78. doi: 10.1093/nar/gki315. Print 2005.
4
Hydroquinone-O,O'-diacetic acid ('Q-linker') as a replacement for succinyl and oxalyl linker arms in solid phase oligonucleotide synthesis.对苯二酚 - O,O'-二乙酸(“Q 连接体”)在固相寡核苷酸合成中作为琥珀酰和草酰连接臂的替代物。
Nucleic Acids Res. 1997 Sep 15;25(18):3629-35. doi: 10.1093/nar/25.18.3629.

本文引用的文献

1
Minimum Muscle-Tension Change Trajectories Predicted by Using a 17-Muscle Model of the Monkey's Arm.使用猴子手臂的17肌肉模型预测的最小肌肉张力变化轨迹
J Mot Behav. 1996 Jun;28(2):83-100. doi: 10.1080/00222895.1996.9941736.
2
Cellular uptake of oligodeoxyribonucleoside methylphosphonates.
Antisense Res Dev. 1995 Winter;5(4):251-9. doi: 10.1089/ard.1995.5.251.
3
Cell-type specific and ligand specific enhancement of cellular uptake of oligodeoxynucleoside methylphosphonates covalently linked with a neoglycopeptide, YEE(ah-GalNAc)3.
Bioconjug Chem. 1995 Nov-Dec;6(6):695-701. doi: 10.1021/bc00036a006.
4
Characterization of hybridization between synthetic oligodeoxynucleotides and RNA in living cells.活细胞中合成寡脱氧核苷酸与RNA杂交的表征
Nucleic Acids Res. 1995 Dec 25;23(24):4946-53. doi: 10.1093/nar/23.24.4946.
5
Deprotection of methylphosphonate oligonucleotides using a novel one-pot procedure.使用一种新型一锅法对甲基膦酸酯寡核苷酸进行脱保护。
Nucleic Acids Res. 1993 May 11;21(9):2031-8. doi: 10.1093/nar/21.9.2031.
6
The application of the AMB protective group in the solid-phase synthesis of methylphosphonate DNA analogues.AMB保护基团在甲基膦酸酯DNA类似物固相合成中的应用。
Nucleic Acids Res. 1993 Jul 25;21(15):3493-500. doi: 10.1093/nar/21.15.3493.
7
Functionalization of oligonucleotides with amino groups and attachment of amino specific reporter groups.用氨基对寡核苷酸进行功能化修饰以及连接氨基特异性报告基团。
Methods Mol Biol. 1994;26:93-120. doi: 10.1007/978-1-59259-513-6_3.
8
Solid-phase synthesis of oligonucleotides containing site-specific N-(2'-deoxyguanosin-8-yl)-2-(acetylamino)fluorene adducts using 9-fluorenylmethoxycarbonyl as the base-protecting group.以9-芴甲氧羰基作为碱基保护基团,固相合成含位点特异性N-(2'-脱氧鸟苷-8-基)-2-(乙酰氨基)芴加合物的寡核苷酸。
Biochemistry. 1993 Dec 21;32(50):14043-52. doi: 10.1021/bi00213a038.
9
Delivery of antisense oligodeoxyribonucleotides against the human epidermal growth factor receptor into cultured KB cells with liposomes conjugated to folate via polyethylene glycol.通过聚乙二醇将叶酸偶联脂质体用于向培养的KB细胞中递送针对人表皮生长因子受体的反义寡脱氧核糖核苷酸。
Proc Natl Acad Sci U S A. 1995 Apr 11;92(8):3318-22. doi: 10.1073/pnas.92.8.3318.
10
The synthesis, characterization and biological properties of a new substance, 5-fluoropyrimidine-2-one.
Biochim Biophys Acta. 1964 Jun 22;87(2):353-5. doi: 10.1016/0926-6550(64)90236-1.