• 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

己糖核苷类似物掺入寡核苷酸：合成、碱基配对特性及酶稳定性

Incorporation of hexose nucleoside analogues into oligonucleotides: synthesis, base-pairing properties and enzymatic stability.

作者信息

Augustyns K, Vandendriessche F, Van Aerschot A, Busson R, Urbanke C, Herdewijn P

机构信息

Laboratory of Pharmaceutical Chemistry, Rega Institute for Medical Research, Leuven.

出版信息

Nucleic Acids Res. 1992 Sep 25;20(18):4711-6. doi: 10.1093/nar/20.18.4711.

DOI:10.1093/nar/20.18.4711
PMID:1329028
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC334221/
Abstract

Oligonucleotides containing 1-(2,4-dideoxy-beta-D-erythro-hexopyranosyl)thymine (2) and 1-(3,4-dideoxy-beta-D-erythro-hexopyranosyl)thymine (3) were synthesized on a solid support using the phosphoramidite approach. The properties of these oligonucleotides were compared with the earlier reported characteristics of oligonucleotides containing 1-(2,3-dideoxy-beta-D-erythro-hexopyranosyl) thymine (1). The order in enzymatic stability of end-substituted oligonucleotides is 3 greater than 1 much greater than 2. The hybridization properties of the modified oligonucleotides are in reverse order: 2 much greater than 1 greater than 3.

摘要

采用亚磷酰胺法在固相载体上合成了含有1-(2,4-二脱氧-β-D-赤藓糖己吡喃糖基)胸腺嘧啶(2)和1-(3,4-二脱氧-β-D-赤藓糖己吡喃糖基)胸腺嘧啶(3)的寡核苷酸。将这些寡核苷酸的性质与早期报道的含有1-(2,3-二脱氧-β-D-赤藓糖己吡喃糖基)胸腺嘧啶(1)的寡核苷酸的特征进行了比较。末端取代寡核苷酸的酶稳定性顺序为3大于1远大于2。修饰寡核苷酸的杂交性质顺序相反：2远大于1大于3。

相似文献

1
Incorporation of hexose nucleoside analogues into oligonucleotides: synthesis, base-pairing properties and enzymatic stability.己糖核苷类似物掺入寡核苷酸：合成、碱基配对特性及酶稳定性
Nucleic Acids Res. 1992 Sep 25;20(18):4711-6. doi: 10.1093/nar/20.18.4711.
2
Sugar modified oligonucleotides: synthesis, nuclease resistance and base pairing of oligodeoxynucleotides containing 1-(4'-thio-beta-D-ribofuranosyl)-thymine.糖修饰的寡核苷酸：含1-(4'-硫代-β-D-呋喃核糖基)-胸腺嘧啶的寡脱氧核苷酸的合成、核酸酶抗性及碱基配对
Biochem Biophys Res Commun. 1992 Apr 30;184(2):797-803. doi: 10.1016/0006-291x(92)90660-d.
3
Synthesis, incorporation into triplex-forming oligonucleotide, and binding properties of a novel 2'-deoxy-C-nucleoside featuring a 6-(thiazolyl-5)benzimidazole nucleobase.一种具有6-(噻唑基-5)苯并咪唑碱基的新型2'-脱氧-C-核苷的合成、掺入三链形成寡核苷酸及其结合特性
Org Lett. 2002 Nov 28;4(24):4209-12. doi: 10.1021/ol026609h.
4
Synthesis and properties of aminopropyl nucleic acids.氨丙基核酸的合成与性质
Chembiochem. 2005 Dec;6(12):2298-304. doi: 10.1002/cbic.200500170.
5
Synthesis and hybridization properties of l-oligodeoxynucleotide analogues fixed in a low anti glycosyl conformation.固定在低抗糖基构象的L-寡脱氧核苷酸类似物的合成及杂交特性
Org Biomol Chem. 2004 Jan 21;2(2):183-9. doi: 10.1039/b312276j. Epub 2003 Dec 10.
6
Oligonucleotides containing a new type of acyclic, achiral nucleoside analogue: 1-[3-hydroxy-2-(hydroxymethyl)prop-1-enyl]thymine.含有新型无环、非手性核苷类似物的寡核苷酸：1-[3-羟基-2-(羟甲基)丙-1-烯基]胸腺嘧啶。
Bioorg Med Chem Lett. 2003 Mar 10;13(5):847-50. doi: 10.1016/s0960-894x(03)00008-8.
7
Synthesis and biophysical studies of modified oligonucleotides containing acyclic amino alcohol nucleoside analogs.
Nucleosides Nucleotides. 1999 Aug;18(8):1845-61. doi: 10.1080/07328319908044847.
8
Synthesis and incorporation of tricyclic-imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine nucleosides into oligonucleotides and their thermal stability.三环咪唑并[5',4':4,5]吡啶并[2,3-d]嘧啶核苷的合成、掺入寡核苷酸及其热稳定性。
Nucleic Acids Symp Ser. 1997(37):23-4.
9
Hybridization specificity, enzymatic activity and biological (Ha-ras) activity of oligonucleotides containing 2,4-dideoxy-beta-D-erythro-hexopyranosyl nucleosides.含有2,4-二脱氧-β-D-赤式-己吡喃糖基核苷的寡核苷酸的杂交特异性、酶活性及生物学（Ha-ras）活性
Nucleic Acids Res. 1993 Oct 11;21(20):4670-6. doi: 10.1093/nar/21.20.4670.
10
6-aza-2'-deoxyisocytidine: synthesis, properties of oligonucleotides, and base-pair stability adjustment of DNA with parallel strand orientation.6-氮杂-2'-脱氧异胞苷：合成、寡核苷酸性质以及具有平行链取向的DNA碱基对稳定性调节
J Org Chem. 2003 Jan 24;68(2):367-77. doi: 10.1021/jo020507n.

引用本文的文献

1
Ru-catalyzed sequence for the synthesis of cyclic amido-ethers.用于合成环状酰胺醚的钌催化序列
Chem Sci. 2017 Jan 1;8(1):770-774. doi: 10.1039/c6sc02849g. Epub 2016 Sep 12.
2
Dideoxy fluoro-ketopyranosyl nucleosides as potent antiviral agents: synthesis and biological evaluation of 2,3- and 3,4-dideoxy-3-fluoro-4- and -2-keto-beta-d-glucopyranosyl derivatives of N(4)-benzoyl cytosine.双脱氧氟代酮吡喃糖基核苷作为强效抗病毒剂：N(4)-苯甲酰胞嘧啶的2,3-和3,4-双脱氧-3-氟-4-和-2-酮-β-D-吡喃葡萄糖基衍生物的合成及生物学评价
Eur J Med Chem. 2009 Jun;44(6):2696-704. doi: 10.1016/j.ejmech.2009.01.020. Epub 2009 Jan 29.
3
Preorganization of DNA: Design Principles for Improving Nucleic Acid Recognition by Synthetic Oligonucleotides.DNA的预组织：通过合成寡核苷酸改善核酸识别的设计原则。
Chem Rev. 1997 Aug 5;97(5):1473-1488. doi: 10.1021/cr9603791.
4
Hybrid characteristics of oligonucleotides consisting of isonucleoside 2',5'-anhydro-3'-deoxy-3'-(thymin-1-yl)-D-mannitol with different linkage modes.具有不同连接方式的由异核苷2',5'-脱水-3'-脱氧-3'-(胸腺嘧啶-1-基)-D-甘露糖醇组成的寡核苷酸的杂交特性
Nucleic Acids Res. 2001 Apr 1;29(7):1470-5. doi: 10.1093/nar/29.7.1470.
5
DNA duplexes with reactive dialdehyde groups as novel reagents for cross-linking to restriction- modification enzymes.具有反应性二醛基团的DNA双链体作为用于与限制修饰酶交联的新型试剂。
Nucleic Acids Res. 1997 Aug 15;25(16):3302-9. doi: 10.1093/nar/25.16.3302.
6
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.
7
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.
8
An expression based clonality assay at the human androgen receptor locus (HUMARA) on chromosome X.一种基于X染色体上人类雄激素受体基因座（HUMARA）的表达克隆性分析。
Nucleic Acids Res. 1994 Feb 25;22(4):697-8. doi: 10.1093/nar/22.4.697.
9
Incorporation of 2'-amido-nucleosides in oligodeoxynucleotides and oligoribonucleotides as a model for 2'-linked conjugates.将2'-氨基核苷掺入寡脱氧核苷酸和寡核糖核苷酸中作为2'-连接缀合物的模型。
Nucleic Acids Res. 1995 Jan 11;23(1):51-7. doi: 10.1093/nar/23.1.51.
10
Hybridization specificity, enzymatic activity and biological (Ha-ras) activity of oligonucleotides containing 2,4-dideoxy-beta-D-erythro-hexopyranosyl nucleosides.含有2,4-二脱氧-β-D-赤式-己吡喃糖基核苷的寡核苷酸的杂交特异性、酶活性及生物学（Ha-ras）活性
Nucleic Acids Res. 1993 Oct 11;21(20):4670-6. doi: 10.1093/nar/21.20.4670.

本文引用的文献

1
Base-base mismatches. Thermodynamics of double helix formation for dCA3XA3G + dCT3YT3G (X, Y = A,C,G,T).碱基-碱基错配。dCA3XA3G + dCT3YT3G（X、Y = A、C、G、T）双螺旋形成的热力学
Nucleic Acids Res. 1985 Jul 11;13(13):4811-24. doi: 10.1093/nar/13.13.4811.
2
Predicting DNA duplex stability from the base sequence.根据碱基序列预测DNA双链稳定性。
Proc Natl Acad Sci U S A. 1986 Jun;83(11):3746-50. doi: 10.1073/pnas.83.11.3746.
3
Derivatization of controlled pore glass beads for solid phase oligonucleotide synthesis.用于固相寡核苷酸合成的可控孔径玻璃珠的衍生化
Biotechniques. 1988 Sep;6(8):768-75.
4
Uncharged stereoregular nucleic acid analogs: 2. Morpholino nucleoside oligomers with carbamate internucleoside linkages.不带电荷的立体规整核酸类似物：2. 具有氨基甲酸酯核苷间连接的吗啉代核苷寡聚物。
Nucleic Acids Res. 1989 Aug 11;17(15):6129-41. doi: 10.1093/nar/17.15.6129.
5
Sugar modified oligonucleotides. I. Carbo-oligodeoxynucleotides as potential antisense agents.糖修饰的寡核苷酸。I. 碳寡脱氧核苷酸作为潜在的反义剂。
Biochem Biophys Res Commun. 1989 Dec 15;165(2):742-7. doi: 10.1016/s0006-291x(89)80029-4.
6
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.
7
Biochemical properties of oligo [(+)-carbocyclic-thymidylates] and their complexes.寡聚[（+）-碳环胸苷酸]及其复合物的生化特性。
Nucleic Acids Res. 1990 Apr 25;18(8):2133-40. doi: 10.1093/nar/18.8.2133.
8
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.
9
Sequence-selective recognition of DNA by strand displacement with a thymine-substituted polyamide.通过胸腺嘧啶取代的聚酰胺进行链置换对DNA的序列选择性识别
Science. 1991 Dec 6;254(5037):1497-500. doi: 10.1126/science.1962210.
10
Synthesis and base-pairing properties of the nuclease-resistant alpha-anomeric dodecaribonucleotide alpha-[r(UCUUAACCCACA)].耐核酸酶的α-异头十二聚核糖核苷酸α-[r(UCUUAACCCACA)]的合成及碱基配对特性
Nucleic Acids Res. 1992 Mar 25;20(6):1193-200. doi: 10.1093/nar/20.6.1193.