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1,N6-乙烯基腺苷酸和1,N6-乙烯基-2'-脱氧腺苷酸作为兔骨骼肌糖原磷酸化酶激活位点的探针。

1,N6-etheno-AMP and 1,N6-etheno-2'-deoxy-AMP as probes of the activator site of glycogen phosphorylase from rabbit skeletal muscle.

作者信息

Vandenbunder B, Morange M, Buc H

出版信息

Proc Natl Acad Sci U S A. 1976 Aug;73(8):2696-700. doi: 10.1073/pnas.73.8.2696.

DOI:10.1073/pnas.73.8.2696
PMID:1066682
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC430715/
Abstract

Both 1,N6-etheno-AMP and 1,N6-etheno-2'-deoxy-AMP bind at the AMP site of phosphorylase b (1,4-alpha-D-glucan:orthophosphate alpha-glucosyltransferase, EC 2.4.1.1). Etheno-AMP induces the same activation as AMP, about 30-fold higher than the activation induced by etheno-dAMP. The fluorescence of etheno-AMP and etheno-dAMP is associated with the base moiety; therefore, when free in solution, the two derivatives have identical fluorescence properties. However, when bound to phosphorylase, the fluorescence of etheno-AMP is quenched more efficiently than the fluorescence of etheno-dAMP. This difference between the fluorescence properties of the bound nucleotides suggests that a modification in the ribose ring affects the position of the adenine in the AMP site of phosphorylase b. The observed quenching may be due to a stacking interaction between an aromatic residue and the base moiety of the bound nucleotide.

摘要

1,N6-乙烯基腺苷酸(1,N6-etheno-AMP)和1,N6-乙烯基-2'-脱氧腺苷酸(1,N6-etheno-2'-deoxy-AMP)均结合于磷酸化酶b(1,4-α-D-葡聚糖:正磷酸α-葡糖基转移酶,EC 2.4.1.1)的腺苷酸位点。乙烯基腺苷酸诱导的激活作用与腺苷酸相同,比乙烯基脱氧腺苷酸诱导的激活作用高约30倍。乙烯基腺苷酸和乙烯基脱氧腺苷酸的荧光与碱基部分相关;因此,当它们在溶液中游离时,这两种衍生物具有相同的荧光特性。然而,当与磷酸化酶结合时,乙烯基腺苷酸的荧光比乙烯基脱氧腺苷酸的荧光更有效地猝灭。结合核苷酸荧光特性的这种差异表明,核糖环的修饰会影响磷酸化酶b腺苷酸位点中腺嘌呤的位置。观察到的猝灭可能是由于芳香族残基与结合核苷酸的碱基部分之间的堆积相互作用所致。

相似文献

1
1,N6-etheno-AMP and 1,N6-etheno-2'-deoxy-AMP as probes of the activator site of glycogen phosphorylase from rabbit skeletal muscle.1,N6-乙烯基腺苷酸和1,N6-乙烯基-2'-脱氧腺苷酸作为兔骨骼肌糖原磷酸化酶激活位点的探针。
Proc Natl Acad Sci U S A. 1976 Aug;73(8):2696-700. doi: 10.1073/pnas.73.8.2696.
2
Synthesis of AMP analogs and their use for studies on the allosteric site of rabbit muscle glycogen phosphorylase b.AMP类似物的合成及其在兔肌肉糖原磷酸化酶b变构位点研究中的应用。
J Biochem. 1977 May;81(5):1401-11.
3
Circular dichroism studies on glycogen phosphorylase from rabbit muscle. Interaction with the allosteric activator adenosine 5'-monophosphate.兔肌肉糖原磷酸化酶的圆二色性研究。与变构激活剂5'-单磷酸腺苷的相互作用。
Biochemistry. 1976 Oct 5;15(20):4438-46. doi: 10.1021/bi00665a016.
4
A comparison of the activator sites of liver and muscle glycogen phosphorylase b.肝脏和肌肉糖原磷酸化酶b激活位点的比较。
J Biol Chem. 1982 Dec 10;257(23):14041-7.
5
Interaction of glycogen phosphorylase with 8-azidoadenosine 5'-monophosphate, a photoaffinity analog of AMP.糖原磷酸化酶与8-叠氮腺苷5'-单磷酸(一种AMP的光亲和类似物)的相互作用。
Biochim Biophys Acta. 1980 Mar 14;612(1):195-204. doi: 10.1016/0005-2744(80)90293-4.
6
Determination of sites in rabbit muscle glycogen phosphorylase b modified by an adenosine 5'-monophosphate analog, N6-p-bromoacetaminobenzyladenosine-5'-phosphate.兔肌肉糖原磷酸化酶b中被腺苷5'-单磷酸类似物N6-p-溴乙酰氨基苄基腺苷-5'-磷酸修饰位点的测定
J Biochem. 1978 Dec;84(6):1507-11. doi: 10.1093/oxfordjournals.jbchem.a132275.
7
31P nuclear magnetic resonance studies of glycogen phosphorylase from rabbit skeletal muscle: ionization states of pyridoxal 5'-phosphate.兔骨骼肌糖原磷酸化酶的31P核磁共振研究:磷酸吡哆醛的电离状态
Proc Natl Acad Sci U S A. 1977 Mar;74(3):856-60. doi: 10.1073/pnas.74.3.856.
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Comparative study of the interactions AMP-phosphorylase b and AMP analogues-phosphorylase b.AMP-磷酸化酶b与AMP类似物-磷酸化酶b相互作用的比较研究。
Enzyme. 1985;34(2):83-93. doi: 10.1159/000469367.
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Potato and rabbit muscle phosphorylases: comparative studies on the structure, function and regulation of regulatory and nonregulatory enzymes.马铃薯和兔肌肉磷酸化酶:调节型和非调节型酶的结构、功能及调节的比较研究
Mol Cell Biochem. 1982 Feb 19;42(3):129-44. doi: 10.1007/BF00238507.
10
Spin-labelled AMP - an activator of phosphorylase.自旋标记的AMP——磷酸化酶的激活剂。
Eur J Biochem. 1976 Mar 16;63(1):33-8. doi: 10.1111/j.1432-1033.1976.tb10203.x.

本文引用的文献

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The activity of -adenosine derivatives as allosteric modifiers of phosphorylase b.β-腺苷衍生物作为磷酸化酶b变构调节剂的活性。
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Fluorescent modification of adenosine-containing coenzymes. Biological activities and spectroscopic properties.含腺苷辅酶的荧光修饰。生物活性和光谱性质。
Biochemistry. 1972 Sep 12;11(19):3499-506. doi: 10.1021/bi00769a001.
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Probes for the conformational transitions of phosphorylase b. Effect of ligands studied by proton relaxation enhancement, fluorescence and chemical reactivities.磷酸化酶b构象转变的探针。通过质子弛豫增强、荧光和化学反应性研究配体的作用。
Eur J Biochem. 1971 Jun 29;20(4):494-508. doi: 10.1111/j.1432-1033.1971.tb01419.x.
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AMP analogs: their function in the activation of glycogen phosphorylase b.AMP类似物:它们在糖原磷酸化酶b激活中的作用。
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10
Dynamic and static quenching of 1,N6-ethenoadenine fluorescence in nicotinamide 1,N6-ethenoadenine dinucleotide and in 1,N6-etheno-9-(3-(indol-3-yl) propyl) adenine.烟酰胺1,N6-乙烯腺嘌呤二核苷酸及1,N6-乙烯基-9-(3-(吲哚-3-基)丙基)腺嘌呤中1,N6-乙烯腺嘌呤荧光的动态与静态猝灭
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