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适用于光亲和标记实验的荧光鸟苷酸类似物。

Fluorescent guanosine-nucleotide analogs suitable for photoaffinity-labeling experiments.

作者信息

Wiegand G, Kaleja R

出版信息

Eur J Biochem. 1976 Jun 1;65(2):473-9. doi: 10.1111/j.1432-1033.1976.tb10363.x.

DOI:10.1111/j.1432-1033.1976.tb10363.x
PMID:949978
Abstract

The synthesis and properties of strongly fluorescent derivative of inosine and its nucleotides are described. Reaction of 2-chloro-inosinic acid with sodium azide leads to a product bearing the tetrazole ring between position 2 and 3. Methylation at N1 was effected with dimethyl sulfate. The corresponding nucleosides and their 5'-triphosphates were also prepared. Only the non-methylated series is at equilibrium with small concentrations of their azido forms, and can be photolyzed by wavelengths above 300 nm. Both series are strongly fluorescent, their emission and excitation fluorescence spectra, as well as their quantum yields were measured. The nucleoside 5'-triphosphates are able to initiate and sustain polymerization of porcine brain tubulin.

摘要

描述了肌苷及其核苷酸的强荧光衍生物的合成与性质。2-氯肌苷酸与叠氮化钠反应生成在2位和3位之间带有四唑环的产物。用硫酸二甲酯在N1位进行甲基化。还制备了相应的核苷及其5'-三磷酸酯。只有未甲基化的系列与其叠氮形式的低浓度处于平衡状态,并且可以被300 nm以上的波长光解。两个系列都具有强荧光,测量了它们的发射和激发荧光光谱以及量子产率。核苷5'-三磷酸酯能够引发并维持猪脑微管蛋白的聚合。

相似文献

1
Fluorescent guanosine-nucleotide analogs suitable for photoaffinity-labeling experiments.适用于光亲和标记实验的荧光鸟苷酸类似物。
Eur J Biochem. 1976 Jun 1;65(2):473-9. doi: 10.1111/j.1432-1033.1976.tb10363.x.
2
Synthesis of fluorescent nucleotide analogues: 5'-mono-, di-, and triphosphates of linear-benzoguanosine, linear-benzoinosine, and linear-benzoxanthosine.荧光核苷酸类似物的合成:线性苯并鸟苷、线性苯并肌苷和线性苯并黄苷的5'-单磷酸、二磷酸和三磷酸。
Proc Natl Acad Sci U S A. 1979 Sep;76(9):4262-4. doi: 10.1073/pnas.76.9.4262.
3
Synthesis and use of azido photoaffinity analogs of adenine and guanine nucleotides.腺嘌呤和鸟嘌呤核苷酸的叠氮光亲和类似物的合成与应用。
Methods Enzymol. 1979;56:642-53. doi: 10.1016/0076-6879(79)56061-3.
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Imidazo(1,2-c)pyrimidine nucleosides. Synthesis of N-bridgehead inosine monophosphate and guanosine monophosphate analogues related to 3-deazapurines.咪唑并(1,2 - c)嘧啶核苷。与3 - 脱氮嘌呤相关的N - 桥头肌苷一磷酸和鸟苷一磷酸类似物的合成。
J Org Chem. 1975 Dec 12;40(25):3708-13. doi: 10.1021/jo00913a019.
5
Polynucleotides. XV. Synthesis and properties of polynucleotides containing N 2 -dimethylguanylic acid residues in polyinosinate and polyadenylate chains.多核苷酸。十五。在聚肌苷酸和聚腺苷酸链中含有N2-二甲基鸟苷酸残基的多核苷酸的合成与性质。
Biochim Biophys Acta. 1972 Nov 16;287(1):9-15. doi: 10.1016/0005-2787(72)90325-5.
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Synthesis, azido-tetrazole equilibrium studies and biological activity of 1-(2-azido-6-chloropyrid-4-yl)-3-phenylurea, a photoaffinity labeling reagent for cytokinin-binding proteins.1-(2-叠氮基-6-氯吡啶-4-基)-3-苯基脲(一种用于细胞分裂素结合蛋白的光亲和标记试剂)的合成、叠氮-四唑平衡研究及生物活性
Bioorg Med Chem. 1995 Apr;3(4):361-6. doi: 10.1016/0968-0896(95)00035-f.
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Interaction of tubulin with ribose-modified analogs of GTP and GDP: evidence for two mutually exclusive exchangeable nucleotide binding sites.微管蛋白与核糖修饰的GTP和GDP类似物的相互作用:存在两个相互排斥的可交换核苷酸结合位点的证据。
Proc Natl Acad Sci U S A. 1981 Jun;78(6):3368-72. doi: 10.1073/pnas.78.6.3368.
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Synthesis and properties of nucleoside 5'-phosphoazidates derived from guanosine and adenosine nucleotides: effective on elongation factors G and Tu dependent reactions.
Biochemistry. 1977 Sep 20;16(19):4312-9. doi: 10.1021/bi00638a029.
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Inosine-coated bacteriophage T 4 .肌苷包被的噬菌体T4
Biochim Biophys Acta. 1971 Jul 29;240(4):604-10.
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Use of nucleotide photoaffinity probes to study hormone action.使用核苷酸光亲和探针研究激素作用。
Biol Reprod. 1983 Feb;28(1):61-73. doi: 10.1095/biolreprod28.1.61.

引用本文的文献

1
Synthesis and biological properties of C-2 triazolylinosine derivatives.C-2 三唑基肌苷衍生物的合成及生物活性。
J Org Chem. 2012 Jul 20;77(14):5870-83. doi: 10.1021/jo300628y. Epub 2012 Jul 3.
2
The interaction of chromophoric nucleotides with subfragment 1 of myosin.发色核苷酸与肌球蛋白亚片段1的相互作用。
Biochem J. 1977 Apr 1;163(1):15-29. doi: 10.1042/bj1630015.