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生物缀合中的芳基化反应

Arylation Chemistry for Bioconjugation.

机构信息

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA, 02139, USA.

The Skaggs Institute for Chemical Biology and Department of Molecular Medicine, The Scripps Research Institute, La Jolla, CA, 92037, USA.

出版信息

Angew Chem Int Ed Engl. 2019 Apr 1;58(15):4810-4839. doi: 10.1002/anie.201806009. Epub 2019 Feb 15.

DOI:10.1002/anie.201806009
PMID:30399206
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6433541/
Abstract

Bioconjugation chemistry has been used to prepare modified biomolecules with functions beyond what nature intended. Central to these techniques is the development of highly efficient and selective bioconjugation reactions that operate under mild, biomolecule compatible conditions. Methods that form a nucleophile-sp carbon bond show promise for creating bioconjugates with new modifications, sometimes resulting in molecules with unparalleled functions. Here we outline and review sulfur, nitrogen, selenium, oxygen, and carbon arylative bioconjugation strategies and their applications to modify peptides, proteins, sugars, and nucleic acids.

摘要

生物共轭化学被用于制备具有超出自然预期功能的修饰生物分子。这些技术的核心是开发高效和选择性的生物共轭反应,这些反应在温和的、与生物分子相容的条件下进行。形成亲核试剂-碳键的方法显示出在生物共轭物中引入新修饰的潜力,有时会产生具有无与伦比功能的分子。在这里,我们概述并回顾了硫、氮、硒、氧和碳芳基化生物共轭策略及其在修饰肽、蛋白质、糖和核酸中的应用。

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Chem Sci. 2017 Nov 13;9(2):336-344. doi: 10.1039/c7sc04292b. eCollection 2018 Jan 14.
6
Site-Specific Incorporation of Chemical Fluorescence on Live Enterovirus-71 Virion by Using an Organometallic Palladium Reagent To Monitor Virus Entry.利用有机金属钯试剂在活的肠道病毒71型病毒体上进行化学荧光的位点特异性掺入以监测病毒进入
Chembiochem. 2018 Jul 16;19(14):1465-1470. doi: 10.1002/cbic.201800051. Epub 2018 May 18.
7
A general strategy for synthesis of cyclophane-braced peptide macrocycles via palladium-catalysed intramolecular sp C-H arylation.通过钯催化的分子内 sp C-H 芳基化反应合成环芳撑支撑的肽大环的一般策略。
Nat Chem. 2018 May;10(5):540-548. doi: 10.1038/s41557-018-0006-y. Epub 2018 Apr 2.
8
Post-transcriptional labeling by using Suzuki-Miyaura cross-coupling generates functional RNA probes.通过使用 Suzuki-Miyaura 交叉偶联进行转录后标记可生成功能性 RNA 探针。
Nucleic Acids Res. 2018 Jun 20;46(11):e65. doi: 10.1093/nar/gky185.
9
Perfluoroaryl Bicyclic Cell-Penetrating Peptides for Delivery of Antisense Oligonucleotides.全氟芳基双环细胞穿透肽用于反义寡核苷酸的递送。
Angew Chem Int Ed Engl. 2018 Apr 16;57(17):4756-4759. doi: 10.1002/anie.201801167. Epub 2018 Mar 14.
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Rational Tuning of Fluorobenzene Probes for Cysteine-Selective Protein Modification.理性调控氟苯探针用于半胱氨酸选择性蛋白质修饰。
Angew Chem Int Ed Engl. 2018 Jul 2;57(27):8022-8026. doi: 10.1002/anie.201712589. Epub 2018 Apr 14.