A Visible-Light-Driven O-Glycosylation with Selenoglycosides Mediated by Chalcogen Bonding to Umemoto's Reagent
Dr. Erik Alvarez Valenzuela
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803 USA
Both authors contributed equally to this work.
Search for more papers by this authorDr. Tiffany Duong
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803 USA
Both authors contributed equally to this work.
Search for more papers by this authorVinayak Pradeep
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803 USA
Search for more papers by this authorProf. Xuxian He
Department of Chemistry and Physical Sciences, Nicholls St. University, 906 East 1st St., Thibodaux, LA, 70301 USA
Search for more papers by this authorJacob M. Dobson
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803 USA
Search for more papers by this authorProf. Semin Lee
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803 USA
Search for more papers by this authorProf. Kenneth Lopata
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803 USA
Search for more papers by this authorCorresponding Author
Prof. Justin R. Ragains
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803 USA
E-mail: [email protected]
Search for more papers by this authorDr. Erik Alvarez Valenzuela
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803 USA
Both authors contributed equally to this work.
Search for more papers by this authorDr. Tiffany Duong
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803 USA
Both authors contributed equally to this work.
Search for more papers by this authorVinayak Pradeep
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803 USA
Search for more papers by this authorProf. Xuxian He
Department of Chemistry and Physical Sciences, Nicholls St. University, 906 East 1st St., Thibodaux, LA, 70301 USA
Search for more papers by this authorJacob M. Dobson
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803 USA
Search for more papers by this authorProf. Semin Lee
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803 USA
Search for more papers by this authorProf. Kenneth Lopata
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803 USA
Search for more papers by this authorCorresponding Author
Prof. Justin R. Ragains
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803 USA
E-mail: [email protected]
Search for more papers by this authorAbstract
The activation of chalcogenoglycosides for O-glycosylation typically involves strong electrophiles requiring low temperature. Herein, we demonstrate that visible-light irradiation of selenoglycosides in the presence of Umemoto's reagent results in often high-yielding O-glycosylation. We provide evidence that this process is mediated by a novel mode of reactivity, specifically photoinduced electron transfer within a chalcogen-bonded complex.
Conflict of Interests
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
Supporting Information
| Filename | Description |
|---|---|
| ange202508424-sup-0001-SuppMat.pdf5.8 MB | Supporting Information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1J. D. C. Codée, R. E. J. N. Litjens, L. J. van den Bos, H. S. Overkleeft, G. A. van der Marel, Chem. Soc. Rev. 2005, 34, 769.
- 2K. M. Koeller, C.-H. Wong, Chem. Rev. 2000, 100, 4465–4494.
- 3L. Meng, P. Wu, J. Fang, Y. Xiao, X. Xiao, G. Tu, X. Ma, S. Teng, J. Zeng, Q. Wan, J. Am. Chem. Soc. 2019, 141, 11775–11780.
- 4T. Duong, E. A. Valenzuela, J. R. Ragains, Org. Lett. 2023, 25, 8526–8529.
- 5J. R. Ragains, in Comprehensive Glycoscience – 2nd Edition (Ed: J. Barchi), Elsevier, Amsterdam, 2021, pp. 327–364.
10.1016/B978-0-12-819475-1.00053-5 Google Scholar
- 6J. R. Ragains, in Selective Glycosylations – Synthetic Methods and Catalysts (Ed: C. Bennett), Wiley-VCH, Weinheim, 2017, pp. 211–230.
10.1002/9783527696239.ch10 Google Scholar
- 7R. Sangwan, P. K. Mandal, RSC Adv. 2017, 7, 26256.
- 8Z. Azeem, P. K. Mandal, Adv. Synth. Catal. 2023, 365, 2818–2849.
- 9D. J. Gorelik, S. P. Desai, S. Jdanova, J. A. Turner, M. S. Taylor, Chem. Sci. 2024, 15, 1204–1236.
- 10J. Zhang, Z.-X. Luo, X. Wu, C.-F. Gao, P.-Y. Wang, J.-Z. Chai, M. Liu, X.-S. Ye, D.-C. Xiong, Nat. Commun. 2023, 14, e8025.
- 11W. Yao, D.-C. Xiong, Y. Yang, C. Geng,, Z. Cong, F. Li, B.-H. Li, X. Qin, L.-N. Wang, W.-Y. Xue, H. Zhang, X. Wu, M. Liu, X.-S. Ye, Nature Synthesis 2022, 1, 854–863.
- 12P. H. Seeberger, Acc. Chem. Res. 2015, 48, 1450–1463.
- 13M. L. Spell, K. Deveaux, C. G. Bresnahan, B. L. Bernard, W. Sheffield, R. Kumar, J. R. Ragains, Angew. Chem. Int. Ed. 2016, 55, 6515–6519.
- 14C. Zhang, H. Zuo, G. Y. Lee, Y. Zou, Q.-D. Dang, K. N. Houk, D. Niu, Nat. Chem. 2022, 14, 686–694.
- 15R.-Z. Mao, D.-C. Xiong, F. Guo, Q. Li, J. Duan, X.-S. Ye, Org. Chem. Front. 2016, 3, 737–743.
- 16Y. Yu, D.-C. Xiong, R.-Z. Mao, X.-S. Ye, J. Org. Chem. 2016, 81, 7134–7138.
- 17S. Benz, A. I. Poblador-Bahamonde, N. Low-Ders, S. Matile, Angew. Chem. Int. Ed. 2018, 57, 5408–5412.
- 18G. Cavallo, P. Metrangolo, R. Milani, T. Pilati, A. Priimagi, G. Resnati, G. Terraneo, Chem. Rev. 2016, 116, 2478–2601.
- 19R. Tepper, U. S. Schubert, Angew. Chem. Int. Ed. 2018, 57, 6004–6016.
- 20L. Vogel, P. Wonner, S. M. Huber, Angew. Chem. Int. Ed. 2019, 58, 1880–1891.
- 21K. T. Mahmudov, M. N. Kopylovich, M. F. C. Guedes da Silva, A. J. L. Pombeiro, Dalton Trans. 2017, 46, 10121–10138.
- 22H. A. Bent, Chem. Rev. 1968, 68, 587–648.
- 23C. Xu, V. U. B. Rao, J. Weigen, C. C. J. Loh, Nat. Commun. 2020, 11, Article number: 4911.
- 24C. Xu, C. C. J. Loh, J. Am. Chem. Soc. 2019, 141, 5381–5391.
- 25H. Guo, J.-L. Kirchhoff, C. Strohmann, B. Grabe, C. C. J. Loh, Angew. Chem. Int. Ed. 2024, 63, e202316667.
- 26W. Ma, J.-L. Kirchhoff, C. Strohmann, B. Grabe, C. C. J. Loh, J. Am. Chem. Soc. 2023, 145, 26611–26622.
- 27R. Castelli, S. Schindler, S. M. Walter, F. Kniep, H. S. Overkleeft, G. A. van der Marel, S. M. Huber, J. D. C. Codée, Chem.–Asian J. 2014, 9, 2095–2098.
- 28Y. Lu, Q. Liu, Z.-W. Wang, X.-Y. Chen, Angew. Chem. Int. Ed. 2022, 61, e202116071.
- 29S. V. Rosokha, J. K. Kochi, Acc. Chem. Res. 2008, 41, 641–653.
- 30Y. Wei, Q.-Q. Zhou, F. Tan, L.-Q. Lu, W.-J Xiao, Synthesis 2019, 51, 3021–3054.
- 31G. E. M. Crisenza, D. Mazzarella, P. Melchiorre, J. Am. Chem. Soc. 2020, 142, 5461–5476.
- 32R. M. Rosa, R. Roesler, A. L. Braga, J. Saffi, J. A. P. Henriques, Braz. J. Med. Biol. Res. 2007, 40, 1287–1304.
- 33C. W. Nogueira, F. C. Meotti, E. Curte, C. Pilissao, G. Zeni, J. B. T. Rocha, Toxicology 2003, 183, 29–37.
- 34T. Furuta, K. Takeuchi, M. Iwamura, Chem. Commun. 1996, 157.
- 35I. Cumpstey, D. Crich, J. Carbohydr. Chem. 2011, 30, 469–485.
- 36M. Spell, X. Wang, A. E. Wahba, E. Conner, J. Ragains, Carbohydr. Res. 2013, 369, 42–47.
- 37S. van der Vorm, T. Hansen, H. S. Overkleeft, G. A. van der Marel, J. D.C Codée, Chem. Sci. 2017, 8, 1867–1875.
- 38S.-R. Lu, Y.-H. Lai, J.-H. Chen, C.-Y. Liu, K.-K. T. Mong, Angew. Chem. Int. Ed. 2011, 50, 7315–7320.
- 39B. Watson, O. Grounds, W. Borley, S. V. Rosokha, Phys. Chem. Chem. Phys. 2018, 20, 21999–22007.
- 40F. Li, X. Han, Z. Xu, C. P. Zhang, Org. Lett. 2023, 25, 7884–7889.
- 41R. Robidas, D. L. Reinhard, C. Y. Legault, S. M. Huber, Chem. Rec. 2021, 21, 1912–1927.
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.
