Issue 74, 2014

Primary arylamine-based tyrosine-targeted protein modification

Abstract

Tyrosine-targeted modification is of great interest in the site-specific protein modification applications. Aniline derivatives are attractive molecules for tyrosine-targeted protein modifications through either diazonium coupling or three-component Mannich type reactions. In this report, with BSA as a model protein, primary arylamines were demonstrated to incorporate bioorthogonal azide functionality for further site-specific protein modification via click chemistry, glycans for glyco-engineering, and PEG chains for PEGylation to the protein via tyrosine-targeted modification. The successful primary arylamine-based BSA modifications were confirmed by SDS-PAGE, western blot, and MALDI-TOF mass spectrometry. In comparison, three-component Mannich type reaction affords much higher reaction yields than diazonium coupling reaction in all modifications. Further, this study confirmed the importance of the electron withdrawing substituent on the para position of the phenyl ring for the tyrosine-targeted diazonium coupling reaction.

Graphical abstract: Primary arylamine-based tyrosine-targeted protein modification

Supplementary files

Article information

Article type
Paper
Submitted
06 Jun 2014
Accepted
18 Aug 2014
First published
18 Aug 2014

RSC Adv., 2014,4, 39446-39452

Author version available

Primary arylamine-based tyrosine-targeted protein modification

L. Wang, V. Gruzdys, N. Pang, F. Meng and X. Sun, RSC Adv., 2014, 4, 39446 DOI: 10.1039/C4RA05413J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements