title: Mitsunobu Reaction: A Versatile Tool for PEG End Functionalization.
abstract: 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.
authors: Centre for Injury and Repair, Institute of Inflammation and Repair, University of Manchester, Manchester, M13 9PT, UK.
authors: Richard
authors: R
authors: d'Arcy
authors: Centre for Injury and Repair, Institute of Inflammation and Repair, University of Manchester, Manchester, M13 9PT, UK.|NorthWest Centre for Advanced Drug Delivery (NoWCADD), Manchester School of Pharmacy, University of Manchester, Manchester, M13 9PT, UK.
authors: Nicola
authors: N
authors: Tirelli
mesh_terms: D061565:Cycloaddition Reaction; D008970:Molecular Weight; D010720:Phosphines / Q000737:chemistry; D011092:Polyethylene Glycols / Q000138:chemical synthesis*; D012545:Schiff Bases / Q000737:chemistry
chemical_list: D010720:Phosphines; D012545:Schiff Bases; D011092:Polyethylene Glycols
keywords: Michael-type addition; Mitsunobu reaction; PEG; bioconjugation; click reaction