Gold-catalyzed direct alkynylation of tryptophan in peptides using TIPS-EBX

Scholarly Works

• Liu, X.-Y.; Waser, J. Peptide/Protein Functionalization and Macrocyclization via Alkyne Umpolung with Hypervalent Iodine Reagents. Accounts of chemical research 2025, 58, 2852–2861. doi:10.1021/acs.accounts.5c00451
• Zhao, G.; Guo, C.; Wang, D.; Jia, Z.; Loh, T.-P. Gold-catalyzed selective modification of peptides: synthesis of cyclic and acyclic peptide derivatives. Gold Bulletin 2025, 58. doi:10.1007/s13404-025-00359-9
• Kundu, S. K.; Bandyopadhyay, A.; Sarkar, R. Tryptophan-specific modification and diversification of peptides and proteins. Organic & biomolecular chemistry 2025, 23, 1773–1793. doi:10.1039/d4ob02015d
• Barros, S. A.; Padilla-Salinas, R.; Abdiaj, I. Post-synthetic Chemical Functionalization of Peptides. Comprehensive Organic Synthesis; Elsevier, 2025; pp 304–332. doi:10.1016/b978-0-323-96025-0.00139-3
• Nicolai, S.; Waser, J. 6 Synthesis and Applications of Alkynylbenziodoxol(on)es. Hypervalent Halogens in Organic Synthesis; Georg Thieme Verlag KG, 2025. doi:10.1055/sos-sd-246-00076
• Barahdia, A. S.; Thakare, K. L.; Kaur, L.; Jain, R. Endogenous Group‐Directed Late‐Stage C−H Functionalization of Peptides. Advanced Synthesis & Catalysis 2024, 366, 2844–2858. doi:10.1002/adsc.202400373
• Kopp, A.; Oyama, T.; Ackermann, L. Fluorescent coumarin-alkynes for labeling of amino acids and peptides via manganese(I)-catalyzed C-H alkenylation. Chemical communications (Cambridge, England) 2024, 60, 5423–5426. doi:10.1039/d4cc00361f
• Bandyopadhyay, A.; Biswas, P.; Kundu, S. K.; Sarkar, R. Electrochemistry-enabled residue-specific modification of peptides and proteins. Organic & biomolecular chemistry 2024, 22, 1085–1101. doi:10.1039/d3ob01857a
• Tank, D. H.; Kharat, N. D.; Bajaj, K.; Panda, S. S.; Sakhuja, R. Rhodium‐Catalyzed Regioselective C7Ar‐Functionalization of Tryptophan with Quinones and its Late Stage Peptide Exemplification. Asian Journal of Organic Chemistry 2023, 12. doi:10.1002/ajoc.202300503
• Liu, X.-Y.; Cai, W.; Ronceray, N.; Radenovic, A.; Fierz, B.; Waser, J. Synthesis of Fluorescent Cyclic Peptides via Gold(I)-Catalyzed Macrocyclization. Journal of the American Chemical Society 2023, 145, 26525–26531. doi:10.1021/jacs.3c09261
• Koley, M.; Han, J.; Soloshonok, V. A.; Mojumder, S.; Javahershenas, R.; Makarem, A. External oxidants in gold-catalyzed cross-coupling reactions. Journal of Coordination Chemistry 2023, 77, 1–48. doi:10.1080/00958972.2023.2286182
• Zielke, F. M.; Rutjes, F. P. J. T. Recent Advances in Bioorthogonal Ligation and Bioconjugation. Topics in current chemistry (Cham) 2023, 381, 35. doi:10.1007/s41061-023-00445-6
• Liu, X.-Y.; Ji, X.; Heinis, C.; Waser, J. Peptide-Hypervalent Iodine Reagent Chimeras: Enabling Peptide Functionalization and Macrocyclization. Angewandte Chemie (International ed. in English) 2023, 62, e202306036. doi:10.1002/anie.202306036
• Liu, X.; Ji, X.; Heinis, C.; Waser, J. Peptide‐Hypervalent Iodine Reagent Chimeras: Enabling Peptide Functionalization and Macrocyclization**. Angewandte Chemie 2023, 135. doi:10.1002/ange.202306036
• Oyama, T.; Mendive-Tapia, L.; Cowell, V.; Kopp, A.; Vendrell, M.; Ackermann, L. Late-stage peptide labeling with near-infrared fluorogenic nitrobenzodiazoles by manganese-catalyzed C-H activation. Chemical science 2023, 14, 5728–5733. doi:10.1039/d3sc01868g
• Weng, Y.; Zhan, X.; Zhang, Y.; Lin, W. Palladium-Catalyzed C(sp2)-H Arylation of Peptides Directed by Aspartic Acid. The Journal of organic chemistry 2023, 88, 2334–2343. doi:10.1021/acs.joc.2c02755
• Weng, Y.; Xu, X.; Chen, H.; Zhang, Y.; Zhuo, X. Tandem Electrochemical Oxidative Azidation/Heterocyclization of Tryptophan‐Containing Peptides under Buffer Conditions. Angewandte Chemie 2022, 134. doi:10.1002/ange.202206308
• Weng, Y.; Xu, X.; Chen, H.; Zhang, Y.; Zhuo, X. Tandem Electrochemical Oxidative Azidation/Heterocyclization of Tryptophan-Containing Peptides under Buffer Conditions. Angewandte Chemie (International ed. in English) 2022, 61, e202206308. doi:10.1002/anie.202206308
• Elwahy, A. H. M.; Shaaban, M. R.; Abdelhamid, I. A. Recent advances in the functionalization of azulene through Rh‐, Ir‐, Ru‐, Au‐, Fe‐, Ni‐, and Cu‐catalyzed reactions. Applied Organometallic Chemistry 2022, 36. doi:10.1002/aoc.6772
• Decoene, K. W.; Unal, K.; Staes, A.; Zwaenepoel, O.; Gettemans, J.; Gevaert, K.; Winne, J. M.; Madder, A. Triazolinedione protein modification: from an overlooked off-target effect to a tryptophan-based bioconjugation strategy. Chemical science 2022, 13, 5390–5397. doi:10.1039/d1sc06942j

Explore citations to this article at