• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

水相和生物环境中的有机金属催化:利用金属卡宾的力量

Organometallic catalysis in aqueous and biological environments: harnessing the power of metal carbenes.

作者信息

Gutiérrez Sara, Tomás-Gamasa María, Mascareñas José Luis

机构信息

Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Departamento de Química Orgánica, Universidade de Santiago de Compostela 15705 Santiago de Compostela Spain

出版信息

Chem Sci. 2022 May 16;13(22):6478-6495. doi: 10.1039/d2sc00721e. eCollection 2022 Jun 7.

DOI:10.1039/d2sc00721e
PMID:35756533
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9172117/
Abstract

Translating the power of transition metal catalysis to the native habitats of enzymes can significantly expand the possibilities of interrogating or manipulating natural biological systems, including living cells and organisms. This is especially relevant for organometallic reactions that have shown great potential in the field of organic synthesis, like the metal-catalyzed transfer of carbenes. While, at first sight, performing metal carbene chemistry in aqueous solvents, and especially in biologically relevant mixtures, does not seem obvious, in recent years there has been a growing number of reports demonstrating the feasibility of the task. Either using small molecule metal catalysts or artificial metalloenzymes, a number of carbene transfer reactions that tolerate aqueous and biorelevant media are being developed. This review intends to summarize the most relevant contributions, and establish the state of the art in this emerging research field.

摘要

将过渡金属催化的能力应用于酶的天然环境中,可显著拓展研究或操控包括活细胞和生物体在内的自然生物系统的可能性。这对于在有机合成领域展现出巨大潜力的有机金属反应而言尤为重要,比如金属催化的卡宾转移反应。乍一看,在水性溶剂中,尤其是在与生物相关的混合物中进行金属卡宾化学反应似乎并不容易,但近年来,越来越多的报告证明了这项任务的可行性。无论是使用小分子金属催化剂还是人工金属酶,一系列能够耐受水性和生物相关介质的卡宾转移反应正在被开发出来。本综述旨在总结最相关的研究成果,并确立这一新兴研究领域的现状。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/de7ca700ff5f/d2sc00721e-f20.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/a0c64d0c2aa0/d2sc00721e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/60fd3373561e/d2sc00721e-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/61bf17dd2ea9/d2sc00721e-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/d52c566b357f/d2sc00721e-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/58ef2fc30c99/d2sc00721e-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/360cc1169ff7/d2sc00721e-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/d0968e999a0f/d2sc00721e-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/e34c96370913/d2sc00721e-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/51475759cffd/d2sc00721e-f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/498a58af4ee3/d2sc00721e-f10.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/8ca68d81c8cd/d2sc00721e-f11.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/60d26c7f0fc5/d2sc00721e-f12.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/ea3b8eb82805/d2sc00721e-f13.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/2bbb1db0c5ba/d2sc00721e-f14.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/54492434667f/d2sc00721e-f15.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/381f30bbb5d7/d2sc00721e-f16.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/e4680d2ad07d/d2sc00721e-f17.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/638153783034/d2sc00721e-f18.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/b4e3ebae2a10/d2sc00721e-f19.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/de7ca700ff5f/d2sc00721e-f20.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/a0c64d0c2aa0/d2sc00721e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/60fd3373561e/d2sc00721e-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/61bf17dd2ea9/d2sc00721e-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/d52c566b357f/d2sc00721e-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/58ef2fc30c99/d2sc00721e-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/360cc1169ff7/d2sc00721e-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/d0968e999a0f/d2sc00721e-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/e34c96370913/d2sc00721e-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/51475759cffd/d2sc00721e-f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/498a58af4ee3/d2sc00721e-f10.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/8ca68d81c8cd/d2sc00721e-f11.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/60d26c7f0fc5/d2sc00721e-f12.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/ea3b8eb82805/d2sc00721e-f13.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/2bbb1db0c5ba/d2sc00721e-f14.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/54492434667f/d2sc00721e-f15.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/381f30bbb5d7/d2sc00721e-f16.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/e4680d2ad07d/d2sc00721e-f17.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/638153783034/d2sc00721e-f18.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/b4e3ebae2a10/d2sc00721e-f19.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/9172117/de7ca700ff5f/d2sc00721e-f20.jpg

相似文献

1
Organometallic catalysis in aqueous and biological environments: harnessing the power of metal carbenes.水相和生物环境中的有机金属催化:利用金属卡宾的力量
Chem Sci. 2022 May 16;13(22):6478-6495. doi: 10.1039/d2sc00721e. eCollection 2022 Jun 7.
2
Exporting Homogeneous Transition Metal Catalysts to Biological Habitats.将均相过渡金属催化剂引入生物栖息地。
European J Org Chem. 2022 Aug 26;2022(32):e202200118. doi: 10.1002/ejoc.202200118. Epub 2022 May 12.
3
Transition Metal-Promoted Reactions in Aqueous Media and Biological Settings.过渡金属促进的水相介质和生物环境中的反应。
Chemistry. 2021 Mar 12;27(15):4789-4816. doi: 10.1002/chem.202003927. Epub 2021 Jan 12.
4
Noble-Metal Substitution in Hemoproteins: An Emerging Strategy for Abiological Catalysis.金属卟啉配合物的取代:一种新兴的非生物催化策略。
Acc Chem Res. 2019 Feb 19;52(2):326-335. doi: 10.1021/acs.accounts.8b00586. Epub 2019 Jan 29.
5
Exporting Metal-Carbene Chemistry to Live Mammalian Cells: Copper-Catalyzed Intracellular Synthesis of Quinoxalines Enabled by N-H Carbene Insertions.将金属卡宾化学推向活哺乳动物细胞:通过 N-H 卡宾插入实现铜催化的细胞内喹喔啉合成。
Angew Chem Int Ed Engl. 2021 Sep 27;60(40):22017-22025. doi: 10.1002/anie.202108899. Epub 2021 Aug 26.
6
In vivo organic synthesis by metal catalysts.金属催化剂的体内有机合成。
Bioorg Med Chem. 2021 Sep 15;46:116353. doi: 10.1016/j.bmc.2021.116353. Epub 2021 Aug 8.
7
N-Heterocyclic carbene transition metal complexes for catalysis in aqueous media.用于水相介质中催化的 N-杂环卡宾过渡金属配合物。
Chem Soc Rev. 2012 Nov 7;41(21):7032-60. doi: 10.1039/c2cs35102a. Epub 2012 Jul 30.
8
Transition Metal Catalyzed Insertion Reactions with Donor/Donor Carbenes.过渡金属催化的与给体/给体卡宾的插入反应。
Angew Chem Int Ed Engl. 2021 Mar 22;60(13):6864-6878. doi: 10.1002/anie.202007001. Epub 2020 Oct 6.
9
Carbene Radicals in Transition-Metal-Catalyzed Reactions.过渡金属催化反应中的卡宾自由基
ACS Catal. 2023 Apr 6;13(8):5428-5448. doi: 10.1021/acscatal.3c00591. eCollection 2023 Apr 21.
10
Artificial metalloenzymes based on the biotin-avidin technology: enantioselective catalysis and beyond.基于生物素-亲和素技术的人工金属酶:对映选择性催化及其他。
Acc Chem Res. 2011 Jan 18;44(1):47-57. doi: 10.1021/ar100099u. Epub 2010 Oct 15.

引用本文的文献

1
Streamlined Identification of Metallopeptides for Intracellular Catalysis Using Positionally Addressable Combinatorial Libraries.使用可定位寻址组合文库简化细胞内催化金属肽的鉴定。
ACS Catal. 2025 May 8;15(10):8624-8632. doi: 10.1021/acscatal.5c00525. eCollection 2025 May 16.
2
Fluorescent probes for investigating the internalisation and action of bioorthogonal ruthenium catalysts within Gram-positive bacteria.用于研究生物正交钌催化剂在革兰氏阳性菌内的内化及作用的荧光探针。
RSC Chem Biol. 2024 Oct 15;5(12):1201-13. doi: 10.1039/d4cb00187g.
3
Intracellular Synthesis of Indoles Enabled by Visible-Light Photocatalysis.

本文引用的文献

1
Design and Engineering of Metal Catalysts for Bio-orthogonal Catalysis in Living Systems.用于生命系统中生物正交催化的金属催化剂的设计与工程
ACS Appl Bio Mater. 2020 Aug 17;3(8):4717-4746. doi: 10.1021/acsabm.0c00581. Epub 2020 Jul 27.
2
Synthetic prodrug design enables biocatalytic activation in mice to elicit tumor growth suppression.合成前药设计使生物催化激活在小鼠中引发肿瘤生长抑制。
Nat Commun. 2022 Jan 10;13(1):39. doi: 10.1038/s41467-021-27804-5.
3
Assembly and Evolution of Artificial Metalloenzymes within Nissle 1917 for Enantioselective and Site-Selective Functionalization of C─H and C═C Bonds.
可见光光催化实现吲哚的细胞内合成
J Am Chem Soc. 2024 Feb 7;146(5):2895-2900. doi: 10.1021/jacs.3c13647. Epub 2024 Jan 26.
4
Nano-encapsulated Cu(II) complex as a promising insecticidal for (Diptera: Culicidae).纳米包裹的铜(II)配合物作为一种有前景的杀虫剂用于(双翅目:蚊科)。
Heliyon. 2023 Dec 4;10(1):e23198. doi: 10.1016/j.heliyon.2023.e23198. eCollection 2024 Jan 15.
5
Lewis acid-driven self-assembly of diiridium macrocyclic catalysts imparts substrate selectivity and glutathione tolerance.路易斯酸驱动的二铱大环催化剂自组装赋予底物选择性和谷胱甘肽耐受性。
Chem Sci. 2023 Sep 4;14(37):10264-10272. doi: 10.1039/d3sc02836d. eCollection 2023 Sep 27.
6
Recent Synthetic Advances on the Use of Diazo Compounds Catalyzed by Metalloporphyrins.金属卟啉催化重氮化合物应用的近期合成进展
Molecules. 2023 Sep 18;28(18):6683. doi: 10.3390/molecules28186683.
7
Ruthenium-catalyzed intermolecular alkene-alkyne couplings in biologically relevant media.钌催化的生物相关介质中的分子间烯烃-炔烃偶联反应。
Chem Sci. 2023 May 19;14(23):6408-6413. doi: 10.1039/d3sc01254a. eCollection 2023 Jun 14.
8
Metal complexes for catalytic and photocatalytic reactions in living cells and organisms.用于活细胞和生物体中催化及光催化反应的金属配合物。
Chem Sci. 2022 Dec 2;14(3):409-442. doi: 10.1039/d2sc05672k. eCollection 2023 Jan 18.
在奈瑟 1917 内组装和进化人工金属酶,用于 C─H 和 C═C 键的对映选择性和位点选择性功能化。
J Am Chem Soc. 2022 Jan 19;144(2):883-890. doi: 10.1021/jacs.1c10975. Epub 2022 Jan 5.
4
Nanomaterial-based bioorthogonal nanozymes for biological applications.基于纳米材料的生物正交纳米酶在生物中的应用。
Chem Soc Rev. 2021 Dec 13;50(24):13467-13480. doi: 10.1039/d0cs00659a.
5
Dual-function enzyme catalysis for enantioselective carbon-nitrogen bond formation.双功能酶催化对映选择性碳氮键形成。
Nat Chem. 2021 Dec;13(12):1166-1172. doi: 10.1038/s41557-021-00794-z. Epub 2021 Oct 18.
6
Unnatural biosynthesis by an engineered microorganism with heterologously expressed natural enzymes and an artificial metalloenzyme.通过异源表达天然酶和人工金属酶的工程微生物进行非天然生物合成。
Nat Chem. 2021 Dec;13(12):1186-1191. doi: 10.1038/s41557-021-00801-3. Epub 2021 Oct 14.
7
Enantioselective Synthesis of Chiral Amines via Biocatalytic Carbene N-H Insertion.通过生物催化卡宾N-H插入对映选择性合成手性胺。
ACS Catal. 2020 Oct 2;10(19):10967-10977. doi: 10.1021/acscatal.0c02794. Epub 2020 Aug 31.
8
Modification of Proteins Using Olefin Metathesis.使用烯烃复分解反应对蛋白质进行修饰。
Mater Chem Front. 2020 Apr 1;4(4):1040-1051. doi: 10.1039/c9qm00494g. Epub 2020 Jan 15.
9
In vivo organic synthesis by metal catalysts.金属催化剂的体内有机合成。
Bioorg Med Chem. 2021 Sep 15;46:116353. doi: 10.1016/j.bmc.2021.116353. Epub 2021 Aug 8.
10
Exporting Metal-Carbene Chemistry to Live Mammalian Cells: Copper-Catalyzed Intracellular Synthesis of Quinoxalines Enabled by N-H Carbene Insertions.将金属卡宾化学推向活哺乳动物细胞:通过 N-H 卡宾插入实现铜催化的细胞内喹喔啉合成。
Angew Chem Int Ed Engl. 2021 Sep 27;60(40):22017-22025. doi: 10.1002/anie.202108899. Epub 2021 Aug 26.