Uniform soluble support for the large-scale synthesis of sequence-defined macromolecules. Issue 39 (16th September 2022)

• Record Type: Journal Article
• Authors: De Franceschi, Irene; Mertens, Chiel; Badi, Nezha; Du Prez, Filip
• Is Part Of: Polymer chemistry. Volume 13:Issue 39(2022)
• Page Start: 5616
• Page End: 5624
• Publication Date: 2022-09-16
• Subjects: Polymers -- Periodicals; Macromolecules -- Periodicals; Polymerization -- Periodicals; 547.705
• DOI: 10.1039/d2py00883a
• Languages: English
• ISSNs: 1759-9954

Abstract

Abstract : A monodisperse soluble support is used as an effective tool for the large-scale, liquid-phase synthesis of sequence-defined macromolecules. This uniform support allows for direct characterisation and leads to a single peak in mass spectrometry. Abstract : Herein, a monodisperse soluble support is explored and used as an effective tool for the large-scale, liquid-phase synthesis of sequence-defined macromolecules. This support, based on a benzyl derivative with three long hydrophobic alkyl chains, combines the advantages of solid-phase and soluble support- based synthesis by allowing a straightforward workup after each coupling step and a direct characterisation of the intermediates, without prior cleavage from the support. While the soluble support is used for the multi-gram synthesis of thiolactone-based sequence-defined macromolecules, it can be applied for numerous other synthetic strategies too. Additionally, as it is uniform, it leads to a single peak in mass spectrometry and thus not to a molecular weight distribution as typically observed for standard polymeric soluble supports, thus facilitating the characterisation. To demonstrate the potential for the synthesis of sequence-defined macromolecules on a scale that is sufficient for their introduction in bulk material synthesis, a hexamer is prepared on a 14 g scale. Furthermore, two different cleavable linkers have been attached to the uniform soluble support, hence emphasizing the versatility of this strategy.