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点击反应和硼酸:应用、问题和潜在解决方案。

Click reactions and boronic acids: applications, issues, and potential solutions.

机构信息

Department of Chemistry and Center for Biotechnology and Drug Design, Georgia State University, Atlanta, Georgia 30303, USA.

出版信息

Molecules. 2010 Aug 23;15(8):5768-81. doi: 10.3390/molecules15085768.

DOI:10.3390/molecules15085768
PMID:20733546
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6257766/
Abstract

Boronic acids have been widely used in a wide range of organic reactions, in the preparation of sensors for carbohydrates, and as potential pharmaceutical agents. With the growing importance of click reactions, inevitably they are also applied to the synthesis of compounds containing the boronic acid moiety. However, such applications have unique problems. Chief among them is the issue of copper-mediated boronic acid degradation in copper-assisted [2,3]-cycloadditions involving an alkyne and an azido compound as the starting materials. This review summarizes recent developments, analyzes potential issues, and discusses known as well as possible solutions.

摘要

硼酸已经被广泛应用于各种有机反应中,用于制备碳水化合物传感器,以及作为潜在的药物制剂。随着点击反应的重要性不断增加,硼酸也不可避免地被应用于含有硼酸部分的化合物的合成中。然而,这类应用存在一些独特的问题。其中最主要的问题是铜介导的硼酸在铜辅助的[2,3]-环加成反应中的降解,该反应的起始原料为炔烃和叠氮化合物。本综述总结了最近的发展,分析了潜在的问题,并讨论了已知的和可能的解决方案。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/86fc680f6fff/molecules-15-05768-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/af20184aede8/molecules-15-05768-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/fdae0397907e/molecules-15-05768-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/198f8f35a5e8/molecules-15-05768-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/1c76a847e939/molecules-15-05768-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/2ca4c4bd11ca/molecules-15-05768-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/641430c043fb/molecules-15-05768-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/75fd7c551612/molecules-15-05768-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/e00ea5e90d9d/molecules-15-05768-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/e97834c29d21/molecules-15-05768-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/86fc680f6fff/molecules-15-05768-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/af20184aede8/molecules-15-05768-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/fdae0397907e/molecules-15-05768-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/198f8f35a5e8/molecules-15-05768-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/1c76a847e939/molecules-15-05768-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/2ca4c4bd11ca/molecules-15-05768-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/641430c043fb/molecules-15-05768-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/75fd7c551612/molecules-15-05768-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/e00ea5e90d9d/molecules-15-05768-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/e97834c29d21/molecules-15-05768-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba64/6257766/86fc680f6fff/molecules-15-05768-g008.jpg

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本文引用的文献

1
Cyanide-sensitive fluorescent probes.氰化物敏感荧光探针。
Dyes Pigm. 2005 Jan;64(1):49-55. doi: 10.1016/j.dyepig.2004.04.002. Epub 2004 Jul 14.
2
Rhodium-Catalyzed Addition of Organoboronic Acids to Aldehydes.铑催化有机硼酸与醛的加成反应
Angew Chem Int Ed Engl. 1998 Dec 17;37(23):3279-3281. doi: 10.1002/(SICI)1521-3773(19981217)37:23<3279::AID-ANIE3279>3.0.CO;2-M.
3
Expanding the Potential of DNA for Binding and Catalysis: Highly Functionalized dUTP Derivatives That Are Substrates for Thermostable DNA Polymerases.
乙烯基硼酸作为快速反应、合成易得且稳定的生物正交试剂在 Carboni-Lindsey 反应中的应用。
Angew Chem Int Ed Engl. 2016 Sep 26;55(40):12243-7. doi: 10.1002/anie.201605271. Epub 2016 Sep 8.
4
Synthesis of 1,2,3-triazol-1-yl-methaneboronic acids via click chemistry: an easy access to a new potential scaffold for protease inhibitors.通过点击化学合成1,2,3 - 三唑 - 1 - 基 - 甲烷硼酸:一种简便获得蛋白酶抑制剂新潜在骨架的方法。
European J Org Chem. 2015 Feb 1;2015(5):1075-1083. doi: 10.1002/ejoc.201403408.
5
Estimation of Dipole Moments and Quantum Yield of 5-chloro-2-methoxyphenyl Boronic Acid in Different Solvents Environment.不同溶剂环境中5-氯-2-甲氧基苯硼酸的偶极矩和量子产率估算
J Fluoresc. 2015 May;25(3):745-53. doi: 10.1007/s10895-015-1561-x. Epub 2015 Mar 29.
6
"Estimation of ground and excited state dipole moments of aryl boronic acid derivative by solvatochromic shift method".通过溶剂化显色位移法估算芳基硼酸衍生物的基态和激发态偶极矩
J Fluoresc. 2014 Nov;24(6):1651-9. doi: 10.1007/s10895-014-1452-6. Epub 2014 Sep 18.
拓展DNA结合与催化的潜力:作为耐热DNA聚合酶底物的高度功能化dUTP衍生物
Angew Chem Int Ed Engl. 1998 Nov 2;37(20):2872-2875. doi: 10.1002/(SICI)1521-3773(19981102)37:20<2872::AID-ANIE2872>3.0.CO;2-5.
4
Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids.硼酸催化温和、选择性的不饱和羧酸的[3+2]偶极环加成反应。
Chemistry. 2010 May 10;16(18):5454-60. doi: 10.1002/chem.200903484.
5
A Fluorescent Hydrogen Peroxide Probe Based on a 'Click' Modified Coumarin Fluorophore.一种基于“点击”修饰香豆素荧光团的荧光过氧化氢探针。
Tetrahedron Lett. 2010 Feb 24;51(8):1152-1154. doi: 10.1016/j.tetlet.2009.12.049.
6
Synthesis and carbohydrate binding studies of fluorescent alpha-amidoboronic acids and the corresponding bisboronic acids.荧光α-氨基硼酸及其相应的双硼酸的合成及糖结合研究。
Bioorg Med Chem. 2010 Feb 15;18(4):1449-55. doi: 10.1016/j.bmc.2010.01.017. Epub 2010 Jan 11.
7
Boronic acid-modified DNA that changes fluorescent properties upon carbohydrate binding.硼酸修饰的 DNA,在与碳水化合物结合时会改变荧光性质。
Chem Commun (Camb). 2010 Feb 21;46(7):1073-5. doi: 10.1039/b921163b. Epub 2010 Jan 15.
8
Modifications to the dNTP triphosphate moiety: from mechanistic probes for DNA polymerases to antiviral and anti-cancer drug design.对脱氧核苷三磷酸部分的修饰:从DNA聚合酶的作用机制研究探针到抗病毒和抗癌药物设计。
Biochim Biophys Acta. 2010 May;1804(5):1223-30. doi: 10.1016/j.bbapap.2010.01.005. Epub 2010 Jan 14.
9
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Chem Commun (Camb). 2009 Sep 21(35):5251-3. doi: 10.1039/b909575f. Epub 2009 Aug 6.
10
Click chemistry beyond metal-catalyzed cycloaddition.超越金属催化环加成反应的点击化学。
Angew Chem Int Ed Engl. 2009;48(27):4900-8. doi: 10.1002/anie.200900755.