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新型荧光5'-磷酸胞苷衍生物

New fluorescent cytidine 5'-phosphate derivatives.

作者信息

Kochetkov N K, Shibaev V N, Kost A A, Razjivin A P

出版信息

Nucleic Acids Res. 1976 May;3(5):1341-9. doi: 10.1093/nar/3.5.1341.

Abstract

Interaction of cytidine 5'-phosphate with chloroacetone or p-tosyloxyacetone leads to 2-methyl-5,6-dihydro-5-oxo-6-(5-0-phospho-beta-D-ribofuranosyl)-imidazo/1,2-c/pyrimidine (2-methylethenocytidine 5'-phosphate) whereas analogous reaction with phenacyl bromide produces similar 2-phenyl-derivative. The bicyclic nucleotides obtained showed significant UV absorption at long wavelength where common nucleotides and proteins exhibited no absorption. These derivatives are highly fluorescent when heterocyclic ring is protonated. The absorption and fluorescent properties of the substituted ethenocytidine 5'-phosphoate derivatives seem to be suitable for their use as fluorescent probes or labels in biochemical studies.

摘要

胞苷5'-磷酸与氯丙酮或对甲苯磺酰氧基丙酮相互作用会生成2-甲基-5,6-二氢-5-氧代-6-(5-O-磷酸-β-D-呋喃核糖基)-咪唑并[1,2-c]嘧啶(2-甲基乙烯基胞苷5'-磷酸),而与苯甲酰溴的类似反应则会产生类似的2-苯基衍生物。所得到的双环核苷酸在长波长处显示出显著的紫外吸收,而普通核苷酸和蛋白质在此处无吸收。当杂环被质子化时,这些衍生物具有高度荧光性。取代的乙烯基胞苷5'-磷酸衍生物的吸收和荧光特性似乎适合用作生化研究中的荧光探针或标记物。

相似文献

1
New fluorescent cytidine 5'-phosphate derivatives.新型荧光5'-磷酸胞苷衍生物
Nucleic Acids Res. 1976 May;3(5):1341-9. doi: 10.1093/nar/3.5.1341.
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pH fluorescent probes: chlorinated fluoresceins.pH荧光探针:氯化荧光素
J Fluoresc. 2008 May-Jul;18(3-4):741-7. doi: 10.1007/s10895-007-0305-y. Epub 2007 Dec 21.

本文引用的文献

1
Separation of the phosphoric esters on the filter paper chromatogram.磷酸酯在滤纸色谱上的分离
Nature. 1949 Dec 31;164(4183):1107-12, illust. doi: 10.1038/1641107a0.
3
Specific and fluorescent modifications of cytidine.
J Am Chem Soc. 1973 Feb 21;95(4):1323-8. doi: 10.1021/ja00785a051.
4
Fluorescent adenosine and cytidine derivatives.荧光腺苷和胞苷衍生物
Biochem Biophys Res Commun. 1972 Jan 31;46(2):597-604. doi: 10.1016/s0006-291x(72)80181-5.

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