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辅酶B12的一种前荧光类似物的合成及生物活性

Synthesis and biological activity of a profluorescent analogue of coenzyme B12.

作者信息

Rosendahl M S, Omann G M, Leonard N J

出版信息

Proc Natl Acad Sci U S A. 1982 Jun;79(11):3480-4. doi: 10.1073/pnas.79.11.3480.

Abstract

We describe here the synthesis and chemical properties of linear(lin)-benzoadenosylcobalamin, a coenzyme B12 analogue that has a laterally extended nucleoside in the upper axial position. It is an effective competitive inhibitor of ribonucleotide reductase from Lactobacillus leichmannii. lin-Benzoadenosylcobalamin is nonfluorescent in solution but, on homolytic (light) or heterolytic (acid, cyanide) cleavage of the carbon-cobalt bond, forms fluorescent products. In addition, fluorescence is detectable on binding of the coenzyme analogue to ribonucleotide reductase, and the observed fluorescence polarization of the lin-benzoadenosyl moiety indicates that it is bound loosely to the enzyme when the coenzyme is partially dissociated.

摘要

我们在此描述线性(lin)-苯并腺苷钴胺素的合成及其化学性质,它是一种辅酶B12类似物,在上轴向位置具有横向延伸的核苷。它是莱氏乳杆菌核糖核苷酸还原酶的有效竞争性抑制剂。线性-苯并腺苷钴胺素在溶液中无荧光,但在碳-钴键发生均裂(光照)或异裂(酸、氰化物)时会形成荧光产物。此外,在辅酶类似物与核糖核苷酸还原酶结合时可检测到荧光,并且观察到的线性-苯并腺苷部分的荧光偏振表明,当辅酶部分解离时,它与酶的结合较为松散。

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本文引用的文献

4
Direct halogenation of sugar moiety of nucleosides.核苷糖部分的直接卤化。
Tetrahedron Lett. 1971 Jan(2):87-90. doi: 10.1016/s0040-4039(01)96366-x.
6
Chemical synthesis and properties of analogs of adenosylcobalamin.
Biochemistry. 1974 Jun 18;13(13):2736-40. doi: 10.1021/bi00710a012.
10
Ribonucleoside triphosphate reductase from Lactobacillus leichmannii.
Methods Enzymol. 1978;51:246-59. doi: 10.1016/s0076-6879(78)51034-3.

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