环丙硫酮-膦键的快速生物分子标记。
A Cyclopropenethione-Phosphine Ligation for Rapid Biomolecule Labeling.
出版信息
Org Lett. 2018 Sep 21;20(18):5614-5617. doi: 10.1021/acs.orglett.8b02296. Epub 2018 Sep 12.
Abstract
Cyclopropenethiones are reported as new bioorthogonal reagents. These motifs react readily with substituted phosphines to provide thiocarbonyl adducts. In some cases, the ligations are >300-fold faster than analogous reactions with bioorthogonal cyclopropenones. Dialkyl cyclopropenethiones are also stable in aqueous buffers and can be used for biomolecule labeling in vitro and in cell lysate. The rapid reactivity and biocompatibility of cyclopropenethiones suggest that they will be useful probes for cellular studies.
摘要
环丙叉硫酮被报道为新的生物正交试剂。这些基团可与取代膦快速反应，生成硫羰加合物。在某些情况下，这些连接反应的速度比类似的生物正交环丙酮反应快 300 多倍。二烷基环丙叉硫酮在水缓冲液中也很稳定，可用于体外和细胞裂解物中的生物分子标记。环丙叉硫酮的快速反应性和生物相容性表明，它们将成为细胞研究的有用探针。
相似文献
1
A Cyclopropenethione-Phosphine Ligation for Rapid Biomolecule Labeling.环丙硫酮-膦键的快速生物分子标记。
Org Lett. 2018 Sep 21;20(18):5614-5617. doi: 10.1021/acs.orglett.8b02296. Epub 2018 Sep 12.
2
Chemically triggered crosslinking with bioorthogonal cyclopropenones.化学引发的生物正交环丙烯酮交联反应。
Chem Commun (Camb). 2020 Sep 17;56(74):10883-10886. doi: 10.1039/d0cc04600k.
3
A Bioorthogonal Ligation of Cyclopropenones Mediated by Triarylphosphines.三芳基膦介导的环丙烯酮的生物正交连接。
J Am Chem Soc. 2015 Aug 19;137(32):10036-9. doi: 10.1021/jacs.5b06969. Epub 2015 Aug 7.
4
Cyclopropeniminium Ions Exhibit Unique Reactivity Profiles with Bioorthogonal Phosphines.环丙烯亚胺离子与生物正交膦表现出独特的反应特性。
J Org Chem. 2019 Jun 7;84(11):7443-7448. doi: 10.1021/acs.joc.9b00518. Epub 2019 May 28.
5
Cyclopropenones for Metabolic Targeting and Sequential Bioorthogonal Labeling.环丙烯酮用于代谢靶向和顺序生物正交标记。
J Am Chem Soc. 2017 May 31;139(21):7370-7375. doi: 10.1021/jacs.7b03010. Epub 2017 May 17.
6
Constructing New Bioorthogonal Reagents and Reactions.构建新型生物正交试剂和反应
Acc Chem Res. 2018 May 15;51(5):1073-1081. doi: 10.1021/acs.accounts.7b00606. Epub 2018 May 4.
7
Reduced thione ligation is preferred over neutral phosphine ligation in diiron biomimics regarding electronic functionality: a spectroscopic and computational investigation.就电子功能而言，在二铁仿生化合物中，硫酮连接的还原比中性膦连接更受青睐：一项光谱学与计算研究。
Chem Commun (Camb). 2016 Dec 22;53(2):332-335. doi: 10.1039/c6cc08042a.
8
The lithiation and acyl transfer reactions of phosphine oxides, sulfides and boranes in the synthesis of cyclopropanes.环丙烷合成中氧化膦、硫化物和硼烷的锂化及酰基转移反应
Org Biomol Chem. 2009 Apr 7;7(7):1329-36. doi: 10.1039/b817436a. Epub 2009 Feb 23.
9
Phosphine-mediated stereoselective reductive cyclopropanation of alpha-substituted allenoates with aromatic aldehydes.膦介导的取代的α-丙二烯酸酯与芳香醛的立体选择性还原环丙烷化反应。
Org Lett. 2010 Feb 5;12(3):544-7. doi: 10.1021/ol902747c.
10
Synthesis, structure and reactivity of 4-phosphanylated 1,3-dialkyl-imidazole-2-thiones.4-膦酰基-1,3-二烷基-2-硫代咪唑啉的合成、结构和反应性。
Dalton Trans. 2012 May 7;41(17):5368-76. doi: 10.1039/c2dt12483a. Epub 2012 Mar 7.
引用本文的文献
1
Mutually Orthogonal Bioorthogonal Reactions: Selective Chemistries for Labeling Multiple Biomolecules Simultaneously.相互正交的生物正交反应：同时标记多种生物分子的选择性化学。
Top Curr Chem (Cham). 2024 Jul 6;382(3):24. doi: 10.1007/s41061-024-00467-8.
2
Temperature Dependence of the Ring Opening of Cyclopropene Imines on Thorium Metallocenes.环丙烯亚胺在钍金属茂上开环反应的温度依赖性
Inorg Chem. 2024 May 27;63(21):9572-9578. doi: 10.1021/acs.inorgchem.3c04213. Epub 2024 Mar 12.
3
Recent Advances in Bioorthogonal Ligation and Bioconjugation.生物正交连接和生物缀合的最新进展。
Top Curr Chem (Cham). 2023 Nov 22;381(6):35. doi: 10.1007/s41061-023-00445-6.
4
Phosphine-Catalyzed Dearomative [3 + 2] Cycloaddition of Benzoxazoles with a Cyclopropenone.膦催化苯并恶唑与环丙烯酮的去芳构化[3 + 2]环加成反应。
Org Lett. 2022 Feb 11;24(5):1127-1131. doi: 10.1021/acs.orglett.1c04045. Epub 2022 Jan 27.
5
Enantioselective palladium-catalyzed C(sp)-C(sp) σ bond activation of cyclopropenones by merging desymmetrization and (3 + 2) spiroannulation with cyclic 1,3-diketones.通过将环丙烷酮的去对称化和（3 + 2）螺环化与环状1,3 - 二酮相结合实现对映选择性钯催化的环丙烷酮的C(sp)-C(sp) σ键活化
Chem Sci. 2021 Sep 20;12(41):13737-13743. doi: 10.1039/d1sc04558j. eCollection 2021 Oct 27.
6
Bioorthogonal chemistry.生物正交化学
Nat Rev Methods Primers. 2021;1. doi: 10.1038/s43586-021-00028-z. Epub 2021 Apr 15.
7
Developing bioorthogonal probes to span a spectrum of reactivities.开发一系列具有不同反应活性的生物正交探针。
Nat Rev Chem. 2020;4:476-489. doi: 10.1038/s41570-020-0205-0. Epub 2020 Jul 21.
8
Bioorthogonal Reactions of Triarylphosphines and Related Analogues.三芳基膦及其相关类似物的生物正交反应。
Chem Rev. 2021 Jun 23;121(12):6802-6849. doi: 10.1021/acs.chemrev.1c00014. Epub 2021 Jun 8.
9
Cyclopropeniminium Ions Exhibit Unique Reactivity Profiles with Bioorthogonal Phosphines.环丙烯亚胺离子与生物正交膦表现出独特的反应特性。
J Org Chem. 2019 Jun 7;84(11):7443-7448. doi: 10.1021/acs.joc.9b00518. Epub 2019 May 28.
本文引用的文献
1
Constructing New Bioorthogonal Reagents and Reactions.构建新型生物正交试剂和反应
Acc Chem Res. 2018 May 15;51(5):1073-1081. doi: 10.1021/acs.accounts.7b00606. Epub 2018 May 4.
2
Thioamide Substitution Selectively Modulates Proteolysis and Receptor Activity of Therapeutic Peptide Hormones.硫酰胺取代选择性调节治疗性肽激素的蛋白水解和受体活性。
J Am Chem Soc. 2017 Nov 22;139(46):16688-16695. doi: 10.1021/jacs.7b08417. Epub 2017 Nov 13.
3
Cell-type-specific metabolic labeling of nascent proteomes in vivo.体内新生蛋白质组的细胞类型特异性代谢标记。
Nat Biotechnol. 2017 Dec;35(12):1196-1201. doi: 10.1038/nbt.4016. Epub 2017 Nov 6.
4
The effects of thioamide backbone substitution on protein stability: a study in α-helical, β-sheet, and polyproline II helical contexts.硫代酰胺主链取代对蛋白质稳定性的影响：在α-螺旋、β-折叠和多聚脯氨酸II螺旋环境中的研究。
Chem Sci. 2017 Apr 1;8(4):2868-2877. doi: 10.1039/c6sc05580j. Epub 2017 Feb 8.
5
Cyclopropenones for Metabolic Targeting and Sequential Bioorthogonal Labeling.环丙烯酮用于代谢靶向和顺序生物正交标记。
J Am Chem Soc. 2017 May 31;139(21):7370-7375. doi: 10.1021/jacs.7b03010. Epub 2017 May 17.
6
Site-Specific Bioorthogonal Labeling for Fluorescence Imaging of Intracellular Proteins in Living Cells.活细胞内蛋白质的细胞内荧光成像的位点特异性生物正交标记。
J Am Chem Soc. 2016 Nov 2;138(43):14423-14433. doi: 10.1021/jacs.6b08733. Epub 2016 Oct 21.
7
In Vivo Bioorthogonal Chemistry Enables Local Hydrogel and Systemic Pro-Drug To Treat Soft Tissue Sarcoma.体内生物正交化学使局部水凝胶和系统前药能够治疗软组织肉瘤。
ACS Cent Sci. 2016 Jul 27;2(7):476-82. doi: 10.1021/acscentsci.6b00150. Epub 2016 Jul 13.
8
Orthogonal bioorthogonal chemistries.正交生物正交化学
Curr Opin Chem Biol. 2015 Oct;28:141-9. doi: 10.1016/j.cbpa.2015.07.006. Epub 2015 Aug 10.
9
A Bioorthogonal Ligation of Cyclopropenones Mediated by Triarylphosphines.三芳基膦介导的环丙烯酮的生物正交连接。
J Am Chem Soc. 2015 Aug 19;137(32):10036-9. doi: 10.1021/jacs.5b06969. Epub 2015 Aug 7.
10
Building better bioorthogonal reactions.构建更好的生物正交反应。
Curr Opin Chem Biol. 2014 Aug;21:103-11. doi: 10.1016/j.cbpa.2014.07.002. Epub 2014 Aug 1.
Zotero 插件