• 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

通过直接光介导的 C-H 功能化从蛋白氨基酸衍生物快速合成非蛋白氨基酸的最新进展。

Recent Advances in Rapid Synthesis of Non-proteinogenic Amino Acids from Proteinogenic Amino Acids Derivatives via Direct Photo-Mediated C-H Functionalization.

机构信息

Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, China.

School of Pharmaceutical Science, Jiangnan University, Wuxi 214122, China.

出版信息

Molecules. 2020 Nov 12;25(22):5270. doi: 10.3390/molecules25225270.

DOI:10.3390/molecules25225270
PMID:33198166
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7696505/
Abstract

Non-proteinogenic amino acids have attracted tremendous interest for their essential applications in the realm of biology and chemistry. Recently, rising C-H functionalization has been considered an alternative powerful method for the direct synthesis of non-proteinogenic amino acids. Meanwhile, photochemistry has become popular for its predominant advantages of mild conditions and conservation of energy. Therefore, C-H functionalization and photochemistry have been merged to synthesize diverse non-proteinogenic amino acids in a mild and environmentally friendly way. In this review, the recent developments in the photo-mediated C-H functionalization of proteinogenic amino acids derivatives for the rapid synthesis of versatile non-proteinogenic amino acids are presented. Moreover, postulated mechanisms are also described wherever needed.

摘要

非蛋白氨基酸因其在生物学和化学领域的重要应用而引起了极大的关注。最近，C-H 功能化反应被认为是直接合成非蛋白氨基酸的另一种有效方法。同时，光化学因其条件温和、能量守恒等显著优点而受到青睐。因此，C-H 功能化和光化学已经被结合起来，以温和环保的方式合成各种非蛋白氨基酸。在这篇综述中，介绍了近年来通过光介导的蛋白氨基酸衍生物的 C-H 功能化反应来快速合成多功能非蛋白氨基酸的最新进展。此外，在需要的地方还描述了假定的反应机制。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/5e5594c29404/molecules-25-05270-sch044.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/61cad080bea8/molecules-25-05270-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/6fc0f7fa97c2/molecules-25-05270-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/27fcfee1771b/molecules-25-05270-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/caa2e78811d9/molecules-25-05270-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/7911e3d98f9b/molecules-25-05270-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/963e91adc6bb/molecules-25-05270-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/34b9335389ae/molecules-25-05270-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/39469359dd2d/molecules-25-05270-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/a2f2388d8b58/molecules-25-05270-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/42b8b3d75f04/molecules-25-05270-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/8b3967fcebfd/molecules-25-05270-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/6b8890cedc15/molecules-25-05270-sch011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/1ee1cb001e25/molecules-25-05270-sch012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/2a98be742443/molecules-25-05270-sch013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/8d52b3244e18/molecules-25-05270-sch014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/a5566849711c/molecules-25-05270-sch015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/cb1b53e2cddf/molecules-25-05270-sch016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/8534bd856fbc/molecules-25-05270-sch017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/6f84548c9890/molecules-25-05270-sch018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/47c82ed3a723/molecules-25-05270-sch019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/8657d217356c/molecules-25-05270-sch020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/706221392f85/molecules-25-05270-sch021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/d473ed214b4d/molecules-25-05270-sch022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/1286b359d6c2/molecules-25-05270-sch023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/0c99339b40a7/molecules-25-05270-sch024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/c3c8bba3070d/molecules-25-05270-sch025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/821ce76f34cd/molecules-25-05270-sch026.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/a1ff69265264/molecules-25-05270-sch027.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/2c83678a4cab/molecules-25-05270-sch028.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/3a24b31f407b/molecules-25-05270-sch030.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/313605c8f49b/molecules-25-05270-sch031.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/d576b399a09e/molecules-25-05270-sch032.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/d9f512829568/molecules-25-05270-sch033.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/1a6e9eea6a43/molecules-25-05270-sch034.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/f8387c47df47/molecules-25-05270-sch036.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/82db6f69e812/molecules-25-05270-sch038.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/9b4efef3ebbe/molecules-25-05270-sch040.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/0e34d41acd54/molecules-25-05270-sch042.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/5e5594c29404/molecules-25-05270-sch044.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/61cad080bea8/molecules-25-05270-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/6fc0f7fa97c2/molecules-25-05270-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/27fcfee1771b/molecules-25-05270-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/caa2e78811d9/molecules-25-05270-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/7911e3d98f9b/molecules-25-05270-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/963e91adc6bb/molecules-25-05270-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/34b9335389ae/molecules-25-05270-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/39469359dd2d/molecules-25-05270-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/a2f2388d8b58/molecules-25-05270-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/42b8b3d75f04/molecules-25-05270-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/8b3967fcebfd/molecules-25-05270-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/6b8890cedc15/molecules-25-05270-sch011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/1ee1cb001e25/molecules-25-05270-sch012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/2a98be742443/molecules-25-05270-sch013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/8d52b3244e18/molecules-25-05270-sch014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/a5566849711c/molecules-25-05270-sch015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/cb1b53e2cddf/molecules-25-05270-sch016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/8534bd856fbc/molecules-25-05270-sch017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/6f84548c9890/molecules-25-05270-sch018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/47c82ed3a723/molecules-25-05270-sch019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/8657d217356c/molecules-25-05270-sch020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/706221392f85/molecules-25-05270-sch021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/d473ed214b4d/molecules-25-05270-sch022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/1286b359d6c2/molecules-25-05270-sch023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/0c99339b40a7/molecules-25-05270-sch024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/c3c8bba3070d/molecules-25-05270-sch025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/821ce76f34cd/molecules-25-05270-sch026.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/a1ff69265264/molecules-25-05270-sch027.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/2c83678a4cab/molecules-25-05270-sch028.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/3a24b31f407b/molecules-25-05270-sch030.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/313605c8f49b/molecules-25-05270-sch031.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/d576b399a09e/molecules-25-05270-sch032.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/d9f512829568/molecules-25-05270-sch033.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/1a6e9eea6a43/molecules-25-05270-sch034.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/f8387c47df47/molecules-25-05270-sch036.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/82db6f69e812/molecules-25-05270-sch038.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/9b4efef3ebbe/molecules-25-05270-sch040.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/0e34d41acd54/molecules-25-05270-sch042.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b40c/7696505/5e5594c29404/molecules-25-05270-sch044.jpg

相似文献

1
Recent Advances in Rapid Synthesis of Non-proteinogenic Amino Acids from Proteinogenic Amino Acids Derivatives via Direct Photo-Mediated C-H Functionalization.通过直接光介导的 C-H 功能化从蛋白氨基酸衍生物快速合成非蛋白氨基酸的最新进展。
Molecules. 2020 Nov 12;25(22):5270. doi: 10.3390/molecules25225270.
2
The synthesis of dehydrotryptophan and dehydrotryptophan-containing peptides.去氢色氨酸和含去氢色氨酸肽的合成。
Org Biomol Chem. 2011 Sep 7;9(17):5897-907. doi: 10.1039/c1ob05777d. Epub 2011 Jul 8.
3
Syntheses and Transformations of α-Amino Acids via Palladium-Catalyzed Auxiliary-Directed sp(3) C-H Functionalization.通过钯催化辅助导向的 sp(3) C-H 功能化合成与转化 α-氨基酸。
Acc Chem Res. 2016 Apr 19;49(4):635-45. doi: 10.1021/acs.accounts.6b00022. Epub 2016 Mar 25.
4
Solid-Phase Peptide Modification via Deaminative Photochemical Csp -Csp Bond Formation Using Katritzky Salts.通过使用 Katritzky 盐的去氨化光化学 Csp-Csp 键形成进行固相肽修饰。
Chemistry. 2022 Jul 11;28(39):e202201121. doi: 10.1002/chem.202201121. Epub 2022 May 26.
5
Ligand-enabled cross-coupling of C(sp3)-H bonds with arylboron reagents via Pd(II)/Pd(0) catalysis.钯（II）/钯（0）催化通过配体促进的 C(sp3)-H 键与芳基硼试剂的交叉偶联。
Nat Chem. 2014 Feb;6(2):146-50. doi: 10.1038/nchem.1836. Epub 2014 Jan 5.
6
C-H functionalization in the synthesis of amino acids and peptides.氨基酸和肽合成中的碳-氢官能团化反应
Chem Rev. 2014 Sep 24;114(18):8775-806. doi: 10.1021/cr500200x. Epub 2014 Aug 21.
7
The world of beta- and gamma-peptides comprised of homologated proteinogenic amino acids and other components.由同源蛋白质氨基酸和其他成分组成的β-肽和γ-肽世界。
Chem Biodivers. 2004 Aug;1(8):1111-239. doi: 10.1002/cbdv.200490087.
8
Radical-Based Synthesis and Modification of Amino Acids.基于自由基的氨基酸合成与修饰。
Angew Chem Int Ed Engl. 2021 Jan 18;60(3):1098-1115. doi: 10.1002/anie.202010157. Epub 2020 Nov 4.
9
Genetically Encoded Photocaged Proteinogenic and Non-Proteinogenic Amino Acids.基因编码光控蛋白源和非蛋白源氨基酸。
Chembiochem. 2024 Sep 2;25(17):e202400393. doi: 10.1002/cbic.202400393. Epub 2024 Jul 18.
10
Synthetic and Mechanistic Implications of Chlorine Photoelimination in Nickel/Photoredox C(sp)-H Cross-Coupling.镍/光氧化还原 C(sp)-H 交叉偶联中氯光消除的合成和机理意义。
Acc Chem Res. 2021 Feb 16;54(4):988-1000. doi: 10.1021/acs.accounts.0c00694. Epub 2021 Jan 29.

引用本文的文献

1
Phosphine Catalyzed Michael-Type Additions: The Synthesis of Glutamic Acid Derivatives from Arylidene--amino Esters.膦催化的迈克尔型加成反应：由亚芳基氨基酯合成谷氨酸衍生物
Molecules. 2024 Jan 10;29(2):342. doi: 10.3390/molecules29020342.
2
Workability of mRNA Sequencing for Predicting Protein Abundance.mRNA 测序预测蛋白质丰度的可行性。
Genes (Basel). 2023 Nov 11;14(11):2065. doi: 10.3390/genes14112065.
3
Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry.

本文引用的文献

1
Visible-light-induced C(sp)-H activation for a C-C bond forming reaction of 3,4-dihydroquinoxalin-2(1)-one with nucleophiles using oxygen with a photoredox catalyst or under catalyst-free conditions.可见光诱导3,4-二氢喹喔啉-2(1)-酮与亲核试剂发生C-C键形成反应，该反应可使用光氧化还原催化剂或在无催化剂条件下借助氧气进行。
RSC Adv. 2018 May 29;8(35):19580-19584. doi: 10.1039/c8ra03259a. eCollection 2018 May 25.
2
Sulfamides direct radical-mediated chlorination of aliphatic C-H bonds.磺胺类化合物可直接实现自由基介导的脂肪族碳氢键氯化反应。
Chem Sci. 2019 Nov 8;11(1):217-223. doi: 10.1039/c9sc03428e.
3
Pd(II)-Catalyzed C-H Acylation of (Hetero)arenes-Recent Advances.
光化学在有机合成中的技术创新：流动化学、高通量实验、放大和光电化学。
Chem Rev. 2022 Jan 26;122(2):2752-2906. doi: 10.1021/acs.chemrev.1c00332. Epub 2021 Aug 10.
钯（II）催化的（杂）芳基 C-H 酰化反应-最新进展。
Molecules. 2020 Jul 16;25(14):3247. doi: 10.3390/molecules25143247.
4
Photocatalytic Synthesis of Polycyclic Indolones.多环吲哚酮的光催化合成
Chemistry. 2020 Jun 2;26(31):7004-7007. doi: 10.1002/chem.202001324. Epub 2020 May 14.
5
Visible-Light-Induced Metal-/Photocatalyst-Free C-H Bond Imidation of Arenes.可见光诱导的芳烃无金属/无光催化剂C-H键亚胺化反应
Org Lett. 2020 Mar 20;22(6):2235-2239. doi: 10.1021/acs.orglett.0c00433. Epub 2020 Mar 2.
6
Visible-Light-Promoted C(sp )-H Alkylation by Intermolecular Charge Transfer: Preparation of Unnatural α-Amino Acids and Late-Stage Modification of Peptides.可见光促进的 C(sp )-H 烷基化反应：通过分子间电荷转移制备非天然α-氨基酸和肽的后期修饰。
Angew Chem Int Ed Engl. 2020 May 4;59(19):7461-7466. doi: 10.1002/anie.201914555. Epub 2020 Mar 17.
7
Electrophotocatalytic Undirected C-H Trifluoromethylations of (Het)Arenes.（杂）芳烃的光电催化无导向C-H三氟甲基化反应
Chemistry. 2020 Mar 12;26(15):3241-3246. doi: 10.1002/chem.201905774. Epub 2020 Feb 19.
8
Visible Light-Promoted Phosphine-Catalyzed Difluoroalkylation of Arenes and Heterocycles.可见光促进的膦催化芳烃和杂环的二氟烷基化反应
J Org Chem. 2020 Jan 17;85(2):942-951. doi: 10.1021/acs.joc.9b02882. Epub 2020 Jan 3.
9
Site-Tunable C-H Bonds Functionalization by Visible-Light-Induced Radical Translocation of -Alkoxyphthalimides.可见光诱导 - 烷氧基邻苯二甲酰亚胺自由基迁移实现位点可控的 C-H 键官能化反应。
Org Lett. 2019 Nov 15;21(22):9147-9152. doi: 10.1021/acs.orglett.9b03524. Epub 2019 Oct 31.
10
Histidine-Specific Peptide Modification via Visible-Light-Promoted C-H Alkylation.通过可见光促进的 C-H 烷基化反应实现组氨酸特异性肽修饰。
J Am Chem Soc. 2019 Nov 13;141(45):18230-18237. doi: 10.1021/jacs.9b09127. Epub 2019 Nov 1.