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The chemical synthesis of the anticodon loop of an eukaryotic initiator tRNA containing the hypermodified nucleoside N6-/N-threonylcarbonyl/-adenosine/t6A/1.包含超修饰核苷N6-（N-苏氨甲酰）-腺苷（t6A）的真核起始tRNA反密码子环的化学合成。
Nucleic Acids Res. 1978 Jun;5(6):1889-905. doi: 10.1093/nar/5.6.1889.
2
Functional anticodon architecture of human tRNALys3 includes disruption of intraloop hydrogen bonding by the naturally occurring amino acid modification, t6A.人类tRNALys3的功能性反密码子结构包括天然存在的氨基酸修饰t6A对环内氢键的破坏。
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Chemical Synthesis of Oligoribonucleotide (ASL of tRNA T. brucei) Containing a Recently Discovered Cyclic Form of 2-Methylthio-N -threonylcarbamoyladenosine (ms ct A).寡核苷酸的化学合成（T. brucei tRNA 的 ASL），其中包含最近发现的 2-甲基硫代-N-硫代羰基氨酰腺苷的环状形式（ms ct A）。
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Hypermodified nucleoside carboxyl group as a target site for specific tRNA modification.超修饰核苷羧基作为特定tRNA修饰的靶位点。
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Synthesis of oligoribonucleotides containing N6-alkyladenosine and 2-methylthio-N6-alkyladenosine.含N6-烷基腺苷和2-甲硫基-N6-烷基腺苷的寡核糖核苷酸的合成。
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The synthesis of oligoribonucleotides containing N6-alkyladenosines and 2-methylthio-N6-alkyladenosines via post-synthetic modification of precursor oligomers.通过前体寡聚物的合成后修饰合成含N6-烷基腺苷和2-甲硫基-N6-烷基腺苷的寡核糖核苷酸。
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Synthesis of the tRNA(Lys,3) anticodon stem-loop domain containing the hypermodified ms2t6A nucleoside.包含超修饰的ms2t6A核苷的tRNA（赖氨酸，3）反密码子茎环结构域的合成。
J Org Chem. 2002 Jul 26;67(15):5352-8. doi: 10.1021/jo025826t.
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Efficient access to 3'--phosphoramidite derivatives of tRNA related -threonylcarbamoyladenosine (tA) and 2-methylthio- -threonylcarbamoyladenosine (mstA).高效获取与苏氨甲酰腺苷（tA）和2-甲硫基-苏氨甲酰腺苷（mstA）相关的tRNA的3'-亚磷酰胺衍生物。
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A cyclic form of N6-threonylcarbamoyladenosine as a widely distributed tRNA hypermodification.N6-硫代氨甲酰基腺苷的环状形式作为一种广泛分布的 tRNA 超修饰。
Nat Chem Biol. 2013 Feb;9(2):105-11. doi: 10.1038/nchembio.1137. Epub 2012 Dec 16.
3
The synthesis of oligoribonucleotides containing N6-alkyladenosines and 2-methylthio-N6-alkyladenosines via post-synthetic modification of precursor oligomers.通过前体寡聚物的合成后修饰合成含N6-烷基腺苷和2-甲硫基-N6-烷基腺苷的寡核糖核苷酸。
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4
Chromatography on Sephadex LH20 as an efficient purification step after removal of internucleotide 2,2,2-trichloroethyl protective groups from oligoribonucleotide phosphotriesters.从寡核糖核苷酸磷酸三酯上去除核苷酸间的2,2,2-三氯乙基保护基团后，使用葡聚糖凝胶LH20进行色谱分离作为一种有效的纯化步骤。
Nucleic Acids Res. 1980 Mar 11;8(5):1097-105. doi: 10.1093/nar/8.5.1097.
5
The chemical synthesis of oligoribonucleotides VII. A comparison of condensing agents in the coupling of silylated ribonucleosides.寡核糖核苷酸的化学合成VII. 甲硅烷基化核糖核苷偶联中缩合剂的比较。
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The synthesis of oligoribonucleotides. IV. Preparation of dinucleoside phosphates from 2',5'-protected ribonucleoside derivatives.寡核糖核苷酸的合成。IV. 由2',5'-保护的核糖核苷衍生物制备二核苷磷酸酯。
Tetrahedron. 1968 Jan;24(2):639-62. doi: 10.1016/0040-4020(68)88015-9.
2
Deoxy oligonucleotide synthesis via the triester method.通过三酯法合成脱氧寡核苷酸。
J Org Chem. 1973 Jan 26;38(2):245-50. doi: 10.1021/jo00942a011.
3
Synthesis of the anticodon loop of Escherichia coli methionine transfer ribonucleic acid.大肠杆菌甲硫氨酸转移核糖核酸反密码子环的合成
J Am Chem Soc. 1974 Apr 3;96(7):2295-7. doi: 10.1021/ja00814a074.
4
Studies on transfer ribonucleic acids and related compounds. VI. Synthesis of yeast alanine transfer ribonucleic acid 3'-terminal nonanucleotides and 5'-terminal hexanucleotides.转移核糖核酸及相关化合物的研究。VI. 酵母丙氨酸转移核糖核酸3'-末端九核苷酸和5'-末端六核苷酸的合成。
J Am Chem Soc. 1973 Jul 11;95(14):4725-33. doi: 10.1021/ja00795a042.
5
Determination of N-(9-( -D-ribofuranosyl)purin-6-ylcarbamoly)threonine at the picomole level in transfer-RNA.在转移核糖核酸中皮摩尔水平的N-（9-（β-D-呋喃核糖基）嘌呤-6-基氨基甲酰基）苏氨酸的测定
Anal Biochem. 1972 Dec;50(2):327-36. doi: 10.1016/0003-2697(72)90041-3.
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Synthesis of thymidine oligonucleotides by phosphite triester intermediates.通过亚磷酸三酯中间体合成胸苷寡核苷酸。
J Am Chem Soc. 1976 Jun 9;98(12):3655-61. doi: 10.1021/ja00428a045.
7
Nucleoside-3'-phosphotriesters as key intermediates for the oligoribonucleotide synthesis. III. An improved preparation of nucleoside 3'-phosphotriesters, their 1H NMR characterization and new conditions for removal of 2-cyanoethyl group.作为寡核糖核苷酸合成关键中间体的核苷-3'-磷酸三酯。III. 核苷3'-磷酸三酯的改进制备方法、其1H NMR表征以及去除2-氰基乙基的新条件。
Nucleic Acids Res. 1976 Dec;3(12):3397-408. doi: 10.1093/nar/3.12.3397.
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Synthesis of oligoribonucleotides.寡核糖核苷酸的合成
J Am Chem Soc. 1977 Nov 9;99(23):7741-3. doi: 10.1021/ja00465a073.
9
Nucleoside 3'-phosphotriesters as key intermediates for the oligoribonucleotide synthesis. IV. New method for removal of 2,2,2-trichloroethyl group and 31P NMR as a new tool for analysis of deblocking of internucleotide phosphate protecting groups.核苷3'-磷酸三酯作为寡核糖核苷酸合成的关键中间体。IV. 去除2,2,2-三氯乙基基团的新方法以及31P NMR作为分析核苷酸间磷酸保护基团脱保护的新工具。
Nucleic Acids Res. 1977 Jul;4(7):2321-9. doi: 10.1093/nar/4.7.2321.
10
Studies on transfer ribonucleic acids and related compounds. X. synthesis of the yeast tyrosine tRNA 5'-terminal oligonucleotides.转移核糖核酸及相关化合物的研究。X. 酵母酪氨酸tRNA 5'-末端寡核苷酸的合成。
Chem Pharm Bull (Tokyo). 1976 Apr;24(4):570-9. doi: 10.1248/cpb.24.570.

包含超修饰核苷N6-（N-苏氨甲酰）-腺苷（t6A）的真核起始tRNA反密码子环的化学合成。

The chemical synthesis of the anticodon loop of an eukaryotic initiator tRNA containing the hypermodified nucleoside N6-/N-threonylcarbonyl/-adenosine/t6A/1.

作者信息

Adamiak R W, Biała E, Grześkowiak K, Kierzek R, Kraszewski A, Markiewicz W T, Okupniak J, Stawiński J, Wiewiórowski M

出版信息

Nucleic Acids Res. 1978 Jun;5(6):1889-905. doi: 10.1093/nar/5.6.1889.

DOI:10.1093/nar/5.6.1889
PMID:673839
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC342132/
Abstract

In this work, the first example of chemical synthesis of oligoribonucleotide containing the hypermodified nucleoside N6-/N-threonylcarbonyl/-adenosine /t6A/ is presented. Synthesis of the heptamer C-C-C-A-U-t6A-A IX, the sequence of which is related to the anticodon loop of the initiator tRNA from yellow lupine, was achieved by: /i/ phosphotriester block synthesis of suitably protected heptamer VI containing an adenosine unit with a free exo-NH2 group, /ii/ highly effective "one-flask" procedure for the transformation of the free exo-NH2 group of adenosine unit of heptamer VI into a N,N'-disubstituted urea system of t6A of heptamer VII /hypermodification/, and /iii/ final deprotection of VIII /32% total yield/ with the use of a new approach for simultaneous hydrogenolysis /PdO-hydrogen-pyridine/ of the p-nitrobenzyl group and 2,2,2-trichloroethyl groups from carboxyl function of t6A and internucleotide phosphates respectively.

摘要

在本工作中，展示了化学合成含超修饰核苷N6-/N-苏氨甲酰/-腺苷（t6A）的寡核糖核苷酸的首个实例。通过以下步骤实现了七聚体C-C-C-A-U-t6A-A IX的合成，其序列与来自黄羽扇豆的起始tRNA的反密码子环相关：/i/ 对含有游离外氨基的腺苷单元的合适保护的七聚体VI进行磷酸三酯片段合成；/ii/ 将七聚体VI的腺苷单元的游离外氨基高效“一锅法”转化为七聚体VII的t6A的N,N'-二取代脲系统（超修饰）；以及/iii/ 采用一种新方法，同时从t6A的羧基官能团和核苷酸间磷酸酯分别氢解对硝基苄基和2,2,2-三氯乙基，对VIII进行最终脱保护（总产率32%）。