SIOC English
有机化学
高级检索

有机化学 >

0 202507030

DOI: https://doi.org/10.6023/cjoc202507030

研究论文

光催化合成含氮杂芳环非天然氨基酸

  • 任钶 ,
  • 张光露 ,
  • 牛轶凡 ,
  • 王晓萌 ,
  • 陈灿玉 ,
  • 蒋敏
展开
  • 杭州师范大学材料与化学化工学院 浙江杭州 311121
‡作者贡献相同

收稿日期: 2025-07-21

  修回日期: 2025-08-28

  网络出版日期: 2025-09-12

基金资助

杭州师范大学国内访问学者(No.4095C5022521106)杭州师范大学教师发展项目(FX2024069)资助项目.

收起

Photocatalytic Radical-Mediated Synthesis of Unnatural α-Amino Acids from Heteroaryl Aldehydes

  • Ren Ke ,
  • Zhang Guanglu ,
  • Niu Yifan ,
  • Wang Xiaomeng ,
  • Chen Canyu ,
  • Jiang Min
Expand
  • School of Material, Chemistry and Chemical Engineering, University of Hangzhou Normal University, Hangzhou, Zhejiang 311121

Received date: 2025-07-21

  Revised date: 2025-08-28

  Online published: 2025-09-12

Supported by

Domestic Visiting Fellows Program of Hangzhou Normal University (No.4095C5022521106), Teachers’ Professional Development Program of Hangzhou Normal University (FX2024069).

Fold

摘要

非天然氨基酸是重要的非天然化学中间体,然而其合成依然是一个挑战。我们报道了一种以含氮杂环甲醛构建含氮杂芳环非天然氨基酸的方法,该方法实现了一系列含氮杂芳环非天然氨基酸的合成,机理研究表明该反应是一个自由基历程,同时该方法也适用于合成含氮杂芳环的多肽。

关键词： 光催化; 非天然氨基酸; 杂芳甲醛; 酰基自由基; 电子顺磁共振

本文引用格式

任钶 , 张光露 , 牛轶凡 , 王晓萌 , 陈灿玉 , 蒋敏 . 光催化合成含氮杂芳环非天然氨基酸[J]. 有机化学, 0 : 202507030 . DOI: 10.6023/cjoc202507030

Abstract

Non-natural α-amino acids (α-AAs) are pivotal in drug and catalysis, yet their synthesis remains challenges. Here we report a Photocatalytic strategy for the direct construction of N-heteroaryl-containing α-AAs from heteroaryl aldehydes via acyl radical intermediates. This method exhibits exceptional functional group tolerance and enables late-stage diversification of peptides and carbonyl-group derivatization. Mechanistic studies confirm a radical-based pathway, while applications in peptide modification highlight its utility in bioorganic chemistry.

Key words： photocatalytic; non-natural amino acids; heteroaryl aldehydes; acyl radical; electron paramagnetic resonance

参考文献

[1] Bunch L.; Krogsgaard-Larsen, P. in Amino Acids, Peptides and Proteins in Organic Chemistry.2011, 4, 149.
[2] Ambrogelly A.; Palioura S.; Söll, D. Nat. Chem. Biol.2007, 3, 29.
[3] Coppola G. M.; Schuster H. F.Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids. Wiley, New York. 1987.
[4] Fukui S.; Schwarcz R.; Rapoport S. I.; Takada Y.; Smith Q. R.J. Neurochem. 1991, 56, 2007.
[5] Cini M.; Bormetti R.; Marconi M.; Molinari A.; Veneroni O.; Varasi M.; Schwarcz R.; Speciale C.Recent Advances in Tryptophan Research: Tryptophan and Serotonin Pathways. Springer US: Boston, MA. 1996, pp. 535.
[6] Kobayashi S.; Matsubara R.; Nakamura Y.; Kitagawa H.; Sugiura, M. J. Am. Chem. Soc.2003, 125, 2507.
[7] Kobayashi S.; Matsubara R.; Kitagawa H. Org. Lett.2002, 4, 143.
[8] Bretschneider .; Miltz W.; Münster P.; Steglich W. Tetrahedron.1988, 44, 5403.
[9] O'Donnell M. J.; Bennett W. D. Tetrahedron.1988, 44, 5389.
[10] Dalgliesh C.J. Chem. Soc.(Resumed). 1952, pp. 137.
[11] Kobayashi S.; Hamada T.; Manabe, K. J. Am. Chem. Soc.2002, 124, 5640.
[12] Hamada T.; Manabe K.; Kobayashi, S. J. Am. Chem. Soc.2004, 126, 7768.
[13] Jousseaume T.; Wurz N. E.; Glorius, F. Angew. Chem. Int. Ed.2011, 50, 1410.
[14] Vitaku E.; Smith D. T.; Njardarson, J. T. J. Med. Chem.2014, 57, 10257.
[15] Ritchie T. J.; Macdonald S. J. F.; Peace S.; Pickett S. D.; Luscombe, C. N. Med. Chem. Commun.2012, 3, 1062.
[16] Lima P. G.; Caruso R. R. B.; Alves S. O.; Pessôa R. F.; Mendonça-Silva D. L.; Nunes R. J.; Noël F.; Castro N. G.; Costa, P. R. R. Bioorg. Med. Chem. Lett.2004, 14, 4399.
[17] Pellicciari R.; Gallo-Mezo M. A.; Natalini B.; Amer, A. M. Tetrahedron Lett.1992, 33, 3003.
[18] Decker R. H.; Brown R. R.; Price, J. M. J. Biol. Chem.1963, 238, 1049.
[19] Oe Y.; Inoue T.; Kishimoto H.; Sasaki M.; Ohta T.; Furukawa, I. Int. J. Org. Chem.2012, 2, 111.
[20] Xu J.; Liu L.; Yan Z.-C.; Liu Y.; Qin L.; Deng N.; Xu H.-J. Green Chem.2023, 25, 2268.
[21] Aycock R. A.; Vogt D. B.; Jui, N. T. Chem. Sci.2017, 8, 7998.
[22] Cao H.; Kuang Y.; Shi X.; Wong K. L.; Tan B. B.; Kwan J. M.C.; Liu, X.; Wu,[J].Nat. Commun. 2020, 11, 1956.
[23] Angioni S.; Ravelli D.; Emma D.; Dondi D.; Fagnoni M.; Albini, A. Adv. Synth. Catal.2008, 350, 2209.
[24] Qiao L.; Fu X.; Si Y.; Chen X.; Qu L.; Yu B. Green Chem.2022, 24, 5614.
[25] Kuang Y.; Wang K.; Shi X.; Huang X.; Meggers E.; Wu, J. Angew. Chem. Int. Ed.2019, 58, 16859.
[26] Fan X.-Z.; Rong J.-W.; Wu H.-L.; Zhou Q.; Deng H.-P.; Tan J. D.; Xue C.-W.; Wu L.-Z.; Tao H.-R.; Wu, J. Angew. Chem. Int. Ed.2018, 57, 8514.
[27] Yan J.; Cheo H. W.; Teo W. K.; Shi X.; Wu H.; Idres S. B.; Deng L.-W.; Wu, J. J. Am. Chem. Soc.2020, 142, 11357.
[28] Zheng H.; Fan Y.; Blenko A. L.; Lin, W. J. Am. Chem. Soc.2023, 145, 9994.
[29] Yan J.; Tang H.; Kuek E. J. R.; Shi X.; Liu C.; Zhang M.; Piper J. L.; Duan S.; Wu J. Nat. Commun.2021, 12, 7214.
[30] Bhowmick A.; Chatterjee A.; Pathak S. S.; Bhat, R. G. Chem. Commun.2023, 59, 11875.
[31] Gao H.; Guo L.; Zhu Y.; Yang C.; Xia W. Chem. Commun.2023, 59, 2771.
[32] Chinchole A.; Henriquez M. A.; Cortes-Arriagada D.; Cabrera A. R.; Reiser O. ACS Catal.2022, 12, 13549.
[33] Treacy S. M.; Rovis, T. J. Am. Chem. Soc.2021, 143, 2729.
[34] Huang Y.; Han Y.-F.; Zhang C.-L.; Ye S. ACS Catal.2023, 13, 11033.
[35] He X.-J.; Liu Z.; Zhou C.; Wang Y.; Zhang L.-J.; Chen B.; Guo X.-N.; Tung C.-H.; Wu L.-Z. ACS Nano.2025, 19, 14366.
[36] Mantry L.; Gandeepan, P. J. Org. Chem.2025, 90, 6897.
[37] Dong J.; Wang X.; Wang Z.; Song H.; Liu Y.; Wang Q. Chem. Sci.2020, 11, 1026.
[38] Wang X.; Chen Y.; Song H.; Liu Y.; Wang Q.Org. Lett. 2021, 23, 2199.
[39] Meng L.; Yang C.; Dong J.; Wen W.; Chen J.; Fan, B. Org. Chem. Front.2024, 11, 21.
Options
文章导航

/

〈 〉