The Thiol-sulfoxonium Ylide Photo-click Reaction for Bioconjugation

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2023 Feb 6

PMID 36741507

Authors

Chuan Wan

Zhanfeng Hou

Dongyan Yang

Ziyuan Zhou

Hongkun Xu

Yuena Wang

Chuan Dai

Mingchan Liang

Jun Meng

Jiean Chen

Feng Yin

Rui Wang

Zigang Li

Affiliations

Soon will be listed here.

Abstract

Visible-light-mediated methods were heavily studied as a useful tool for cysteine-selective bio-conjugation; however, many current methods suffer from bio-incompatible reaction conditions and slow kinetics. To address these challenges, herein, we report a transition metal-free thiol-sulfoxonium ylide photo-click reaction that enables bioconjugation under bio-compatible conditions. The reaction is highly cysteine-selective and generally finished within minutes with naturally occurring riboflavin derivatives as organic photocatalysts. The catalysts and substrates are readily accessible and bench stable and have satisfactory water solubility. As a proof-of-concept study, the reaction was smoothly applied in chemo-proteomic analysis, which provides efficient tools to explore the druggable content of the human proteome.

Citing Articles

Dual-Performing Vinyltetrazine for Rapid, Selective Bioconjugation and Functionalization of Cysteine Proteins.

Chang M, Xu H, Dong Y, Gnawali G, Bi F, Wang W ACS Chem Biol. 2024; 20(1):153-161.

PMID: 39707969 PMC: 11747768. DOI: 10.1021/acschembio.4c00610.

Expanding the Library of Covalent Cysteine Cathepsin Probes Featuring Sulfoxonium Ylide Electrophiles.

Xu B, Mountford S, Thompson P, Edgington-Mitchell L ACS Omega. 2024; 9(43):43940-43947.

PMID: 39494001 PMC: 11525741. DOI: 10.1021/acsomega.4c07604.

Improving reproducibility through condition-based sensitivity assessments: application, advancement and prospect.

Schafer F, Luckemeier L, Glorius F Chem Sci. 2024; .

PMID: 39263664 PMC: 11382186. DOI: 10.1039/d4sc03017f.

Cysteine-Specific Multifaceted Bioconjugation of Peptides and Proteins Using 5-Substituted 1,2,3-Triazines.

Zuo Q, Li Y, Lai X, Bao G, Chen L, He Z Adv Sci (Weinh). 2024; 11(21):e2308491.

PMID: 38466927 PMC: 11151024. DOI: 10.1002/advs.202308491.

References

Bouchet L, Heredia A, Arguello J, Schmidt L . Riboflavin as Photoredox Catalyst in the Cyclization of Thiobenzanilides: Synthesis of 2-Substituted Benzothiazoles. Org Lett. 2019; 22(2):610-614. DOI: 10.1021/acs.orglett.9b04384. View

Wan C, Wang Y, Lian C, Chang Q, An Y, Chen J . Histidine-specific bioconjugation visible-light-promoted thioacetal activation. Chem Sci. 2022; 13(28):8289-8296. PMC: 9297702. DOI: 10.1039/d2sc02353a. View

Zhang Y, Zang C, An G, Shang M, Cui Z, Chen G . Cysteine-specific protein multi-functionalization and disulfide bridging using 3-bromo-5-methylene pyrrolones. Nat Commun. 2020; 11(1):1015. PMC: 7035330. DOI: 10.1038/s41467-020-14757-4. View

Long T, Liu L, Tao Y, Zhang W, Quan J, Zheng J . Light-Controlled Tyrosine Nitration of Proteins. Angew Chem Int Ed Engl. 2021; 60(24):13414-13422. DOI: 10.1002/anie.202102287. View

Hou Z, Wang D, Li Y, Zhao R, Wan C, Ma Y . A Sulfonium Triggered Thiol-yne Reaction for Cysteine Modification. J Org Chem. 2020; 85(3):1698-1705. DOI: 10.1021/acs.joc.9b02505. View

Sun S, Oliveira B, Jimenez-Oses G, Bernardes G . Radical-Mediated Thiol-Ene Strategy: Photoactivation of Thiol-Containing Drugs in Cancer Cells. Angew Chem Int Ed Engl. 2018; 57(48):15832-15835. PMC: 6391964. DOI: 10.1002/anie.201811338. View

Bisag G, Ruggieri S, Fochi M, Bernardi L . Sulfoxonium ylides: simple compounds with chameleonic reactivity. Org Biomol Chem. 2020; 18(43):8793-8809. DOI: 10.1039/d0ob01822h. View

Waddington M, Zheng X, Stauber J, Moully E, Montgomery H, Saleh L . An Organometallic Strategy for Cysteine Borylation. J Am Chem Soc. 2021; 143(23):8661-8668. PMC: 8437308. DOI: 10.1021/jacs.1c02206. View

Ramirez N, Konig B, Gonzalez-Gomez J . Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis. Org Lett. 2019; 21(5):1368-1373. DOI: 10.1021/acs.orglett.9b00064. View

10.

Dias R, Burtoloso A . Catalyst-Free Insertion of Sulfoxonium Ylides into Aryl Thiols. A Direct Preparation of β-Keto Thioethers. Org Lett. 2016; 18(12):3034-7. DOI: 10.1021/acs.orglett.6b01470. View

11.

Hou X, Kaplaneris N, Yuan B, Frey J, Ohyama T, Messinis A . Ruthenaelectro-catalyzed C-H acyloxylation for late-stage tyrosine and oligopeptide diversification. Chem Sci. 2022; 13(12):3461-3467. PMC: 8943857. DOI: 10.1039/d1sc07267f. View

12.

Mons E, Kim R, van Doodewaerd B, Van Veelen P, Mulder M, Ovaa H . Exploring the Versatility of the Covalent Thiol-Alkyne Reaction with Substituted Propargyl Warheads: A Deciding Role for the Cysteine Protease. J Am Chem Soc. 2021; 143(17):6423-6433. PMC: 8154518. DOI: 10.1021/jacs.0c10513. View

13.

Li B, Kim D, Bloom S, Huang R, Qiao J, Ewing W . Site-selective tyrosine bioconjugation via photoredox catalysis for native-to-bioorthogonal protein transformation. Nat Chem. 2021; 13(9):902-908. DOI: 10.1038/s41557-021-00733-y. View

14.

Kubota K, Dai P, Pentelute B, Buchwald S . Palladium Oxidative Addition Complexes for Peptide and Protein Cross-linking. J Am Chem Soc. 2018; 140(8):3128-3133. PMC: 5831526. DOI: 10.1021/jacs.8b00172. View

15.

Li J, He H, Huang M, Chen Y, Luo Y, Yan K . Iridium-Catalyzed B-H Bond Insertion Reactions Using Sulfoxonium Ylides as Carbene Precursors toward α-Boryl Carbonyls. Org Lett. 2019; 21(22):9005-9008. DOI: 10.1021/acs.orglett.9b03410. View

16.

Parker C, Pratt M . Click Chemistry in Proteomic Investigations. Cell. 2020; 180(4):605-632. PMC: 7087397. DOI: 10.1016/j.cell.2020.01.025. View

17.

Sandfort F, Knecht T, Pinkert T, Daniliuc C, Glorius F . Site-Selective Thiolation of (Multi)halogenated Heteroarenes. J Am Chem Soc. 2020; 142(15):6913-6919. DOI: 10.1021/jacs.0c01630. View

18.

Zhang X, Lu G, Sun M, Mahankali M, Ma Y, Zhang M . A general strategy for synthesis of cyclophane-braced peptide macrocycles via palladium-catalysed intramolecular sp C-H arylation. Nat Chem. 2018; 10(5):540-548. DOI: 10.1038/s41557-018-0006-y. View

19.

Choi H, Kim M, Jang J, Hong S . Visible-Light-Induced Cysteine-Specific Bioconjugation: Biocompatible Thiol-Ene Click Chemistry. Angew Chem Int Ed Engl. 2020; 59(50):22514-22522. DOI: 10.1002/anie.202010217. View

20.

Metrano A, Chinn A, Shugrue C, Stone E, Kim B, Miller S . Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms. Chem Rev. 2020; 120(20):11479-11615. PMC: 8006536. DOI: 10.1021/acs.chemrev.0c00523. View