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4-氯-7-硝基苯并呋咱的高亲电特性及其作为蛋白质标记试剂应用的可能后果。

The highly electrophilic character of 4-chloro-7-nitrobenzofurazan and possible consequences for its application as a protein-labelling reagent.

作者信息

Baines B S, Allen G, Brocklehurst K

出版信息

Biochem J. 1977 Apr 1;163(1):189-92. doi: 10.1042/bj1630189.

DOI:10.1042/bj1630189
PMID:17393
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1164679/
Abstract

4-Chloro-7-nitrobenzofurazan possesses at least one highly electrophilic centre (C-6) that is much more reactive towards nucleophiles than position C-4, the irreversible alkylating site of this reagent. Possible consequences of the electrophilic character of 4-chloro-7-nitrobenzofurazan for its application as a protein-labelling reagent are discussed.

摘要

4-氯-7-硝基苯并呋咱具有至少一个高亲电中心(C-6),该中心对亲核试剂的反应性比该试剂的不可逆烷基化位点C-4高得多。讨论了4-氯-7-硝基苯并呋咱的亲电特性对其作为蛋白质标记试剂应用的可能影响。

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1
The highly electrophilic character of 4-chloro-7-nitrobenzofurazan and possible consequences for its application as a protein-labelling reagent.4-氯-7-硝基苯并呋咱的高亲电特性及其作为蛋白质标记试剂应用的可能后果。
Biochem J. 1977 Apr 1;163(1):189-92. doi: 10.1042/bj1630189.
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The nature of the reaction of an essential tyrosine residue of bovine heart mitochondrial ATPase with 4-chloro-7-nitrobenzofurazan and related compounds.牛心线粒体ATP酶的一个必需酪氨酸残基与4-氯-7-硝基苯并呋喃唑及相关化合物的反应性质。
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Reaction of chicken egg white lysozyme with 7-chloro-4-nitrobenz-2-oxa-1,3-diazole. II. Sites of modification.鸡卵清溶菌酶与7-氯-4-硝基苯并-2-恶唑-1,3-二氮杂茂的反应。II. 修饰位点
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引用本文的文献

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Biochem J. 2000 Nov 1;351 Pt 3(Pt 3):723-33.
2
Differences between the electric fields of the catalytic sites of papain and actinidin detected by using the thiol-located nitrobenzofurazan label as a spectroscopic reporter group.使用巯基定位的硝基苯并呋喃标记作为光谱报告基团检测木瓜蛋白酶和猕猴桃蛋白酶催化位点电场之间的差异。
Biochem J. 1984 Jun 1;220(2):609-12. doi: 10.1042/bj2200609.
3
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4
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Biochem J. 1979 Nov 1;183(2):255-68. doi: 10.1042/bj1830255.
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Benzofuroxan as a thiol-specific reactivity probe. Kinetics of its reactions with papain, ficin, bromelain and low-molecular-weight thiols.苯并呋咱作为一种硫醇特异性反应探针。其与木瓜蛋白酶、无花果蛋白酶、菠萝蛋白酶及低分子量硫醇反应的动力学。
Biochem J. 1977 Dec 1;167(3):799-810. doi: 10.1042/bj1670799.

本文引用的文献

1
The reactivity of SH groups with a fluorogenic reagent.巯基与一种荧光试剂的反应活性。
FEBS Lett. 1970 Feb 25;6(4):346-348. doi: 10.1016/0014-5793(70)80095-3.
2
Investigation of the active site of papain with fluorescent probes.用荧光探针研究木瓜蛋白酶的活性位点。
Biochem J. 1973 Aug;133(4):679-86. doi: 10.1042/bj1330679.
3
Evaluation of benzofuroxan as a chromophoric oxidizing agent for thiol groups by using its reactions with papain, ficin, bromelain and low-molecular-weight thiols.通过苯并呋咱与木瓜蛋白酶、无花果蛋白酶、菠萝蛋白酶及低分子量硫醇的反应来评估其作为硫醇基团发色氧化剂的性能。
Biochem J. 1977 Mar 1;161(3):627-37. doi: 10.1042/bj1610627.
4
Fluorescent and spin label probes of the environments of the sulfhydryl groups of porcine muscle adenylate kinase.猪肌肉腺苷酸激酶巯基基团环境的荧光和自旋标记探针。
J Biol Chem. 1975 Jan 25;250(2):644-52.
5
A method for determining the adenosine triphosphatase content of energy-transducing membranes. reaction of 4-chloro-7-nitrobenzofurazan with the adenosine triphosphatase of bovine heart submitochondrial particles.一种测定能量转换膜中三磷酸腺苷酶含量的方法。4-氯-7-硝基苯并呋咱与牛心亚线粒体颗粒的三磷酸腺苷酶的反应。
Biochem J. 1976 Nov;159(2):347-53. doi: 10.1042/bj1590347.
6
4-Chloro-7-nitrobenzo-2-oxa-1,3-diazole as a reactivity probe for the investigation of the thiol proteinases. evidence that ficin and bromelain may lack carboxyl groups conformationally equivalent to that of aspartic acid-158 of papain.4-氯-7-硝基苯并-2-恶唑-1,3-二氮唑作为研究硫醇蛋白酶的反应性探针。有证据表明,无花果蛋白酶和菠萝蛋白酶可能缺乏与木瓜蛋白酶天冬氨酸-158构象相当的羧基。
Biochem J. 1976 Nov;159(2):235-44. doi: 10.1042/bj1590235.
7
A reporter group delivery system with both absolute and selective specificity for thiol groups and an improved fluorescent probe containing the 7-nitrobenzo-2-oxa-1,3-diazole moiety.一种对硫醇基团具有绝对和选择性特异性的报告基团递送系统以及一种含有7-硝基苯并-2-恶唑-1,3-二氮杂环戊二烯部分的改进型荧光探针。
Biochem J. 1975 Nov;151(2):417-32. doi: 10.1042/bj1510417.