Nucleophilic attack of polyaziactones

摘要

The concept of post-polymerisation modification is particularly important for the preparation of libraries of polymers with identical degrees of polymerisation, and this publication has abstracted numerous articles on the subject. This paper focuses on the use of alkenyl azlactones as an alternative to the activated ester strategy. The electrophilic nature of the azlactone ring means it readily ring opens in the presence of nucleophiles, such as primary amine, alcohols and thiols. Alkenyl azlactones, such as 2-vinyl-4,4-dimethylazlactone (VDMA), have been used in controlled radical polymerisations (briefly reviewed in the introduction here). The polyVDMA scaffold then provides a platform to introduce a variety of amino functionalities into the same polymer and this paper explores the possibilities of polyVDMA scaffolds as reactive precursors for direct and tandem post-polymerisation modifications, with a particular view in this paper towards the preparation of synthetic glycopolymers as anti-adhesion therapies against pathogenic toxins.