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research article

Arginine-Specific Modification of Proteins with Polyethylene Glycol

Gauthier, Marc A.
•
Klok, Harm-Anton  
2011
Biomacromolecules

In this study, the residue-selective modification of proteins with polymers at arginine residues is reported. The difficulty in modifying arginine residues lies in the fact that they are less reactive than lysine residues. Consequently, typical chemo-selective reactions which employ "kinetic" selectivity (active esters, Michael addition, etc.) cannot be used to target these residues. The chemistry exploited herein relies on "thermodynamic" selectivity to achieve selective modification of arginine residues. omega-Methoxy poly(ethylene glycol) bearing an alpha-oxo-aldehyde group was synthesized and used to demonstrate the selective modification of lysozyme at arginine residues. In addition, the optimization of reaction conditions for coupling as well as the stability of the formed adduct toward dilution, toward a nucleophilic buffer, and toward acidification are reported. It was concluded that this approach is a convenient, mild, selective, and catalyst-free method for protein modification.

  • Details
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Type
research article
DOI
10.1021/bm101272g
Web of Science ID

WOS:000287175700025

Author(s)
Gauthier, Marc A.
Klok, Harm-Anton  
Date Issued

2011

Published in
Biomacromolecules
Volume

12

Issue

2

Start page

482

End page

493

Subjects

Noncanonical Amino-Acids

•

Site-Specific Pegylation

•

Reversible Modification

•

Chemical-Modification

•

Dicarbonyl-Compounds

•

Maillard Reaction

•

Block-Copolymers

•

Disulfide Bonds

•

Alpha-Diketone

•

Serum-Albumin

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LP  
Available on Infoscience
March 22, 2011
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/65583
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