Laccase-catalyzed tyrosine click reaction with 1-methyl-4-arylurazole: rapid labeling on protein surfaces

Keita Nakane; Chizu Fujimura; Shogo Miyano; Zhengyi Liu; Tatsuya Niwa; Hafumi Nishi; Tetsuya Kadonosono; Hideki Taguchi; Shusuke Tomoshige; Minoru Ishikawa; Shinichi Sato

doi:10.1039/d4cc03802a

Laccase-catalyzed tyrosine click reaction with 1-methyl-4-arylurazole: rapid labeling on protein surfaces

Chem Commun (Camb). 2024 Nov 28;60(96):14208-14211. doi: 10.1039/d4cc03802a.

Authors

Keita Nakane^{1

2}, Chizu Fujimura¹, Shogo Miyano², Zhengyi Liu¹, Tatsuya Niwa³, Hafumi Nishi^{4

5

6}, Tetsuya Kadonosono⁷, Hideki Taguchi³, Shusuke Tomoshige², Minoru Ishikawa², Shinichi Sato^{1

2}

Affiliations

¹ Frontier Research Institute for Interdisciplinary Sciences, Tohoku University, 6-3 Aramaki aza-Aoba, Aoba-ku, Sendai, Miyagi 980-8578, Japan. [email protected].
² Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai, Miyagi 980-8577, Japan.
³ Cell Biology Center, Institute of Innovative Research, Tokyo Institute of Technology, 4259-S2-19, Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501, Japan.
⁴ Department of Applied Information Sciences, Graduate School of Information Sciences, Tohoku University, 6-3 Aramaki Aza-Aoba, Aoba-ku, Sendai, Miyagi 980-8578, Japan.
⁵ Tohoku Medical Megabank Organization, Tohoku University, 2-1 Seiryo-machi, Aoba-ku, Sendai, Miyagi 980-8573, Japan.
⁶ Faculty of Core Research, Ochanomizu University, 2-1-1 Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan.
⁷ School of Life Science and Technology, Tokyo Institute of Technology, Yokohama, Kanagawa 226-8501, Japan.

PMID: 39531010
DOI: 10.1039/d4cc03802a

Abstract

Our study demonstrates the exceptional efficiency of 1-methyl-4-arylurazole (MAUra) for tyrosine labeling, optimized with laccase under mild conditions, achieving a high efficiency (k_cat/K_m = 7.88 × 10⁴ M^-1 s^-1) with minimal oxidative side reactions and selective labeling of highly exposed tyrosine sites on proteins.

MeSH terms

Biocatalysis
Click Chemistry*
Laccase* / chemistry
Laccase* / metabolism
Molecular Structure
Surface Properties
Tyrosine* / chemistry

Substances

Laccase
Tyrosine