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Mitsunobu Reaction: A Versatile Tool for PEG End Functionalization
Author(s) -
d'Arcy Richard,
Tirelli Nicola
Publication year - 2015
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201500380
Subject(s) - pegylation , mitsunobu reaction , peg ratio , combinatorial chemistry , ethylene glycol , chemistry , surface modification , cycloaddition , cleavage (geology) , organic chemistry , polymer chemistry , polyethylene glycol , materials science , catalysis , finance , economics , fracture (geology) , composite material
The Mitsunobu reaction can be efficiently used for the transformation of poly(ethylene glycol) (PEG) terminal OH group(s) into a variety of functions. In comparison to more classical approaches of PEG functionalization, the main advantage of the Mitsunobu reaction attains to the fact that in one step, with no detrimental effect on PEG integrity (e.g., chain cleavage). Here, its quantitative conversion is demonstrated into derivatives that, either directly or after deprotection, are amenable to (bio)conjugation reactions: azides (Huisgen cycloaddition), aldehydes, primary amines (Schiff base formation and reduction), thiols, and N ‐oxymaleimide (Michael‐type addition). Therefore this reaction is proposed as a general tool for the preparation of functionalities for the purpose of PEGylation, and more generally for (bio)conjugation purposes.