氨基核苷及其衍生物。IV. 3'-氨基-3'-脱氧核苷5'-磷酸酯的合成。
Aminonucleosides and their derivatives. IV. Synthesis of the 3'-amino-3'-deoxynucleoside 5'-phosphates.
作者信息
Azhayev A V, Ozols A M, Bushnev A S, Dyatkina N B, Kochetkova S V, Victorova L S, Kukhanova M K, Krayevsky A A, Gottikh B P
出版信息
Nucleic Acids Res. 1979 Feb;6(2):625-43. doi: 10.1093/nar/6.2.625.
Abstract
A new procedure has been developed for the synthesis of 3'-amino-3'-deoxyribonucleosides of adenine, cytosine and uracil by condensing the trimethylsilylated bases with peracylated 3-azido-3-deoxyribose derivative. The azido group could subsequently be reduced to amino. The 5'-phosphates of these nucleosides have been prepared and the analogues have been tested for their ability to stimulate the ribosome-catalyzed reaction of 3'(2')-O-(N-formylmethionyl) adenosine 5'-phosphate with phenylalanyl-tRNA.
摘要
通过将三甲基硅烷基化碱基与全酰化的3-叠氮基-3-脱氧核糖衍生物缩合，已开发出一种合成腺嘌呤、胞嘧啶和尿嘧啶的3'-氨基-3'-脱氧核糖核苷的新方法。叠氮基随后可被还原为氨基。已制备了这些核苷的5'-磷酸酯，并测试了这些类似物刺激核糖体催化的3'(2')-O-(N-甲酰甲硫氨酰)腺苷5'-磷酸与苯丙氨酰-tRNA反应的能力。
相似文献
1
Aminonucleosides and their derivatives. IV. Synthesis of the 3'-amino-3'-deoxynucleoside 5'-phosphates.氨基核苷及其衍生物。IV. 3'-氨基-3'-脱氧核苷5'-磷酸酯的合成。
Nucleic Acids Res. 1979 Feb;6(2):625-43. doi: 10.1093/nar/6.2.625.
2
Synthesis and separation of diastereomers of deoxynucleoside 5'-O-(1-thio)triphosphates.脱氧核苷5'-O-(1-硫代)三磷酸非对映异构体的合成与分离
Nucleic Acids Res. 1983 Jun 11;11(11):3737-51. doi: 10.1093/nar/11.11.3737.
3
Aminoacyl derivatives of nucleosides, nucleotides, and polynucleotides. 18. Synthesis of 2'(3')-O-aminoacyl derivatives of dinucleoside phosphates.核苷、核苷酸及多核苷酸的氨酰基衍生物。18. 二核苷磷酸酯的2'（3'）-O-氨酰基衍生物的合成。
J Org Chem. 1974 Jul 26;39(15):2187-93. doi: 10.1021/jo00929a010.
4
Synthesis and enzymatic polymerisation of 5-amino-1-(2'-deoxy-beta-D-ribofuranosyl)imidazole-4-carboxamide-5'- triphosphate.5-氨基-1-(2'-脱氧-β-D-呋喃核糖基)咪唑-4-甲酰胺-5'-三磷酸的合成与酶促聚合
Nucleic Acids Res. 1990 Dec 11;18(23):7127-31. doi: 10.1093/nar/18.23.7127.
5
Synthesis and characterization of (d)NTP derivatives substituted with residues of different photoreagents.用不同光试剂残基取代的（d）NTP衍生物的合成与表征
Bioconjug Chem. 1995 Jul-Aug;6(4):352-60. doi: 10.1021/bc00034a003.
6
A new linker group for functionalization of nucleic acids.
Nucleic Acids Symp Ser (Oxf). 2008(52):385-6. doi: 10.1093/nass/nrn196.
7
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.某些嘧啶的3'-氨基-2',3'-二脱氧核糖核苷：合成及生物活性
J Med Chem. 1983 Jun;26(6):891-5. doi: 10.1021/jm00360a019.
8
Biochemical retrosynthesis of 2'-deoxyribonucleosides from glucose, acetaldehyde, and a nucleobase.从葡萄糖、乙醛和一种核苷碱进行2'-脱氧核糖核苷的生物化学逆合成
Appl Microbiol Biotechnol. 2006 Aug;71(5):615-21. doi: 10.1007/s00253-005-0205-5. Epub 2005 Nov 11.
9
Synthesis of novel 3'-azido-3'-deoxy-α-L-ribo configured nucleosides: A comparative study between chemical and chemo-enzymatic methodologies.新型3'-叠氮基-3'-脱氧-α-L-核糖构型核苷的合成：化学法与化学酶法的比较研究
Nucleosides Nucleotides Nucleic Acids. 2018;37(4):217-231. doi: 10.1080/15257770.2018.1460476. Epub 2018 May 3.
10
Expanding the borononucleotide family: synthesis of borono-analogues of dCMP, dGMP and dAMP.拓展硼核苷酸家族：dCMP、dGMP 和 dAMP 的硼类似物的合成。
Org Biomol Chem. 2009 Nov 7;7(21):4369-77. doi: 10.1039/b912616c. Epub 2009 Aug 27.
引用本文的文献
1
New fluorescent dyes in the red region for biodiagnostics.用于生物诊断的新型红色荧光染料。
J Fluoresc. 1995 Sep;5(3):247-61. doi: 10.1007/BF00723896.
2
Neoceptor concept based on molecular complementarity in GPCRs: a mutant adenosine A(3) receptor with selectively enhanced affinity for amine-modified nucleosides.基于GPCRs中分子互补性的新型受体概念：一种对胺修饰核苷具有选择性增强亲和力的突变型腺苷A(3)受体
J Med Chem. 2001 Nov 22;44(24):4125-36. doi: 10.1021/jm010232o.
3
Oligomerization of activated derivatives of 3'-amino-3'-deoxyguanosine on poly(C) and poly(dC) templates.3'-氨基-3'-脱氧鸟苷的活化衍生物在聚（C）和聚（dC）模板上的寡聚化。
Nucleic Acids Res. 1985 Apr 11;13(7):2469-84. doi: 10.1093/nar/13.7.2469.
4
Oligoaminonucleoside phosphoramidates. Oligomerization of dimers of 3'-amino-3'-deoxy-nucleotides (GC and CG) in aqueous solution.寡氨基核苷亚磷酰胺酯。3'-氨基-3'-脱氧核苷酸（GC和CG）二聚体在水溶液中的寡聚化。
Nucleic Acids Res. 1987 Feb 25;15(4):1699-715. doi: 10.1093/nar/15.4.1699.
5
The synthesis of protected 5'-amino-2',5'-dideoxyribonucleoside-3'-O-phosphoramidites; applications of 5'-amino-oligodeoxyribonucleotides.保护型5'-氨基-2',5'-二脱氧核糖核苷-3'-O-亚磷酰胺的合成；5'-氨基寡脱氧核糖核苷酸的应用。
Nucleic Acids Res. 1987 Aug 11;15(15):6181-96. doi: 10.1093/nar/15.15.6181.
6
Thiol reduction of 3'-azidothymidine to 3'-aminothymidine: kinetics and biomedical implications.
Pharm Res. 1988 May;5(5):297-9. doi: 10.1023/a:1015926720740.
本文引用的文献
1
Conformational analysis of the sugar ring in nucleosides and nucleotides. Improved method for the interpretation of proton magnetic resonance coupling constants.核苷和核苷酸中糖环的构象分析。解释质子磁共振耦合常数的改进方法。
J Am Chem Soc. 1973 Apr 4;95(7):2333-44. doi: 10.1021/ja00788a038.
2
A novel procedure for the synthesis of 2'-O-alkyl nucleotides.一种合成2'-O-烷基核苷酸的新方法。
Biochemistry. 1972 Dec 19;11(26):4931-7. doi: 10.1021/bi00776a009.
3
Effect of cytidine-5'-monophosphate on peptidyl transferase activity.5'-胞苷单磷酸对肽基转移酶活性的影响。
FEBS Lett. 1975 Oct 15;58(1):94-8. doi: 10.1016/0014-5793(75)80233-x.
4
Preparation of a substituted 3-acetamido-3-deoxy-D-ribofuranosyl bromide suitable for the synthesis of puromycin analogs.制备适用于嘌呤霉素类似物合成的取代3-乙酰氨基-3-脱氧-D-核糖呋喃糖基溴化物。
Carbohydr Res. 1975 May;41:318-22. doi: 10.1016/s0008-6215(00)87033-0.
5
Amino acids are not all initially attached to the same position on transfer RNA molecules.氨基酸并非一开始都附着在转运RNA分子的同一位置上。
Proc Natl Acad Sci U S A. 1975 Aug;72(8):3044-8. doi: 10.1073/pnas.72.8.3044.
6
A general synthesis of N-glycosides. 6. On the mechanism of the stannic chloride catalyzed silyl Hilbert-Johnson reaction.N-糖苷的一般合成。6. 关于氯化锡催化的硅烷基希尔伯特-约翰逊反应的机理
J Org Chem. 1976 Jun 11;41(12):2084-6. doi: 10.1021/jo00874a002.
Zotero 插件