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Tyrosine-Selective Bioconjugation with Iminoxyl Radicals

preprint
submitted on 10.05.2020 and posted on 12.05.2020 by Katsuya Maruyama, Takashi Ishiyama, Yohei Seki, Kounosuke Oisaki, Motomu Kanai
A novel Tyr-selective protein bioconjugation using the water-soluble persistent iminoxyl radical is described. The conjugation proceeded with high Tyr-selectivity and short reaction time under biocompatible conditions (room temperature in buffered media under air). The stability of the conjugates was tunable depending on the steric hindrance of iminoxyl. The presence of sodium ascorbate and/or light irradiation promoted traceless deconjugation, restoring the native Tyr structure. The method is applied to the synthesis of a protein-dye conjugate and further derivatization to azobenzene-modified peptides.

Funding

JSPS KAKENHI Grant Numbers JP17H01522

JSPS KAKENHI Grant Numbers 20H00489

JSPS KAKENHI Grant Numbers JP18H04239

JSPS KAKENHI Grant Number JP25460008

JSPS KAKENHI Grant Number JP18K06545

Astellas Foundation for Research on Metabolic Disorders

JSPS Fellowship JP15J11454

History

Email Address of Submitting Author

oisaki@mol.f.u-tokyo.ac.jp

Institution

The University of Tokyo

Country

Japan

ORCID For Submitting Author

0000-0002-0499-8168

Declaration of Conflict of Interest

none

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