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转运核糖核酸的修饰核苷。II. 2'-O-甲基胞苷酰（3'-5'）胞苷的合成。

The modified nucleosides of tRNAs. II. Synthesis of 2'-O-methylcytidylyl (3'-5') cytidine.

作者信息

Markiewicz W T, Wiewiórowski M

出版信息

Nucleic Acids Res. 1975 Jun;2(6):951-60. doi: 10.1093/nar/2.6.951.

DOI:10.1093/nar/2.6.951
PMID:167357
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC343481/
Abstract

The synthesis of 2'-O-methylcytidylyl (3'-5')cytidine by the triester method using as protecting groups, 2,2,2-trichloroethyl for phosphate hydroxyl group, p-chlorophenyoxyacetyl for 5-hydroxyl group, methoxymethylidene for 2',3'-cis-diol system, and benzoyl for the exo-amino group of cytidine is presented. The obtained product was characterised by UV, electrophoresis, chromatography and an enzymatic digestion.

摘要

介绍了使用2,2,2-三氯乙基作为磷酸羟基的保护基团、对氯苯氧基乙酰基作为5-羟基的保护基团、甲氧基亚甲基作为2',3'-顺式二醇系统的保护基团以及苯甲酰基作为胞苷的外氨基保护基团，通过三酯法合成2'-O-甲基胞苷酰基(3'-5')胞苷。所得产物通过紫外光谱、电泳、色谱和酶消化进行表征。

相似文献

1
The modified nucleosides of tRNAs. II. Synthesis of 2'-O-methylcytidylyl (3'-5') cytidine.转运核糖核酸的修饰核苷。II. 2'-O-甲基胞苷酰（3'-5'）胞苷的合成。
Nucleic Acids Res. 1975 Jun;2(6):951-60. doi: 10.1093/nar/2.6.951.
2
The effective synthesis of uridylyl/3'-5'/5-methylcytidylyl/3'-5'/guanosine.尿苷酰基/3'-5'/5-甲基胞苷酰基/3'-5'/鸟苷的有效合成。
Nucleic Acids Res. 1976 Mar;3(3):709-20. doi: 10.1093/nar/3.3.709.
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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。
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Modification of cytidine residues with a bisulfite-O-methylhydroxylamine mixture.用亚硫酸氢盐- O-甲基羟胺混合物修饰胞嘧啶残基。
Biochim Biophys Acta. 1974 Mar 8;340(2):153-65.
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Alkylation of cytidine-5'-phosphate: mechanisms of alkylation, influence of O'-alkylation on susceptibility of pyrimidine nucleotides to some nucleolytic enzymes, and synthesis of 2'-O-alkyl polynucleotides.
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Nucleic acids. I. The synthesis of nucleotides and dinucleoside phosphates containing ara-cytidine.核酸。I. 含阿糖胞苷的核苷酸和二核苷磷酸的合成。
J Med Chem. 1967 Sep;10(5):762-73. doi: 10.1021/jm00317a003.
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Alkylation of cytosine glycosides in alkaline medium: a new route to the preparation of O'-alkylated nucleosides and nucleotides of cytosine and uracil.碱性介质中胞嘧啶糖苷的烷基化：制备胞嘧啶和尿嘧啶的O'-烷基化核苷及核苷酸的新途径。
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Biochemistry. 1971 Apr 27;10(9):1521-5. doi: 10.1021/bi00785a002.
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2'-O-methylation of adenosine, guanosine, uridine, and cytidine in RNA of isolated rat liver nuclei.分离的大鼠肝细胞核RNA中腺苷、鸟苷、尿苷和胞苷的2'-O-甲基化
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A new chemical probe for single-stranded RNA.一种用于单链RNA的新型化学探针。
Biochem Biophys Res Commun. 1972 Oct 17;49(2):358-63. doi: 10.1016/0006-291x(72)90418-4.

引用本文的文献

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Synthesis and hybridization studies on two complementary nona(2'-O-methyl)ribonucleotides.两种互补的九聚（2'-O-甲基）核糖核苷酸的合成与杂交研究。
Nucleic Acids Res. 1987 Aug 11;15(15):6131-48. doi: 10.1093/nar/15.15.6131.
2
Synthesis of 3'-phosphates of diribonucleoside monophosphates via phosphotriester intermediates.通过磷酸三酯中间体合成二磷酸核苷单磷酸酯的3'-磷酸酯。
Nucleic Acids Res. 1976 Oct;3(10):2731-47. doi: 10.1093/nar/3.10.2731.

本文引用的文献

1
THE ALKALI-STABLE DINUCLEOTIDE SEQUENCES IN 18S+28S RIBONUCLEATES FROM WHEAT GERM.小麦胚芽18S + 28S核糖核酸中的碱稳定二核苷酸序列。
Can J Biochem. 1964 Jul;42:1011-21. doi: 10.1139/o64-112.
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The synthesis of oligoribonucleotides. II. Methoxymethylidene derivatives of ribonucleosides and 5'-ribonucleotides.寡核糖核苷酸的合成。II. 核糖核苷和5'-核糖核苷酸的甲氧基亚甲基衍生物。
Tetrahedron. 1967 May;23(5):2301-13. doi: 10.1016/0040-4020(67)80067-x.
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The preparation and properties of O-methylated adenosine derivatives.
Biochemistry. 1968 Apr;7(4):1413-20. doi: 10.1021/bi00844a025.
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Nucleic acid related compounds. 1. Methylation and transformation of 4-methoxy-2-pyrimidinone 1- -D-ribofuranoside into 2'-O-methyl nucleoside components of ribonucleic acid, their analogs, and derivatives.核酸相关化合物。1. 4-甲氧基-2-嘧啶酮1-β-D-呋喃核糖苷甲基化并转化为核糖核酸的2'-O-甲基核苷成分、其类似物及衍生物。
Biochemistry. 1971 Sep 14;10(19):3591-7. doi: 10.1021/bi00795a017.
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Nucleic acid related compounds. II. A rapid and quantitative preparation of 2'-0- and 3'-0-methyl nucleosides.
Biochim Biophys Acta. 1971 Aug 26;246(2):341-3. doi: 10.1016/0005-2787(71)90144-4.
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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.
7
[Primary structure of transfer RNA].[转运核糖核酸的一级结构]
Biochimie. 1972;54(2):127-44. doi: 10.1016/s0300-9084(72)80097-x.