Staudinger Reactions for Selective Functionalization of Polysaccharides: A Review

Abstract

Staudinger reactions are frequently highly chemoselective and can occur under very mild conditions, so are attractive methods for efficient functionalization of polysaccharides. This review describes recent investigations that exploit Staudinger-related reactions to effectively alter physical and chemical properties of polysaccharides in order to make them more diversely applicable. Staudinger-related reactions, such as Staudinger reduction, Staudinger ligation, and traceless Staudinger ligation comprise a powerful family of techniques enabling preparation of a wide range of polysaccharide derivatives with excellent chemoselectivity and the potential for excellent regioselectivity when combined with other methods. The remarkably mild conditions of the Staudinger reactions, combined with the abiotic nature of the azide group, make these reactions exceptionally attractive for modification of intact biological entities, including living cells.

Potential applications of hydrophobically modified inulin as an active ingredient in functional foods and drugs - A review

“… Cai et al (2019) , Cho et al (2015) , Huang et al (2019b) , Lee et al (2020) , Liu and Edgar (2015b) , Lu et al (2019) , Ni et al (2019) , Rogge and Stevens (2004) , Singh et al (2019) , Suflet et al (2015) .…”

Recent Advances in the Chemistry of Glycoconjugate Amphiphiles

“…A method of choice for the surface functionalization of liposomes calls on the Staudinger ligation [ 73 ] named after the well-known Staudinger reaction between a phosphine and an azide giving an iminophosphorane which hydrolizes into an amine [ 74 ]. Here, to avoid the iminophosphorane hydrolysis, the phosphine features an electrophilic trap such as a methyl ester producing an amide bond ( Table 3 ) [ 75 , 76 ].…”

Expansion of bioorthogonal chemistries towards site-specific polymer–protein conjugation

“…Because they are biocompatible, non-toxic, biodegradable, and abundant in nature, polysaccharides have been widely used for biomedical applications, including drug and gene delivery, tissue engineering, and cosmetics/food engineering. [213][214][215] Polysaccharide-conjugated polymers have been extensively investigated. These functional groups can be utilized for conjugation to other coupling partners.…”