Articolo in rivista, 2023, ENG, 10.1021/acs.biomac.3c00045

Multi-step Strategies Toward Regioselectively Sulfated M-Rich Alginates

Esposito, Fabiana; Laezza, Antonio; Gargiulo, Valentina; Traboni, Serena; Iadonisi, Alfonso; La Gatta, Annalisa; Schiraldi, Chiara; Bedini, Emiliano

Univ Naples Feder II; Univ Basilicata; Natl Res Council STEMS CNR; Univ Campania Luigi Vanvitelli

Sulfated alginates (ASs), as well as several artificially sulfated polysaccharides, show interesting bioactivities. The key factors for structure-activity relationships studies are the degree of sulfation and the distribution of the sulfate groups along the polysaccharide backbone (sulfation pattern). The former param-eter can often be controlled through stoichiometry, while the latter requires the development of suitable chemical or enzymatic, regioselective methods and is still missing for ASs. In this work, a study on the regioselective installation of several different protecting groups on a D-mannuronic acid enriched (M-rich) alginate is reported in order to develop a semi-synthetic access to regioselectively sulfated AS derivatives. A detailed structural characterization of the obtained ASs revealed that the regiose-lective sulfation could be achieved complementarily at the O-2 or O-3 positions of M units through multi-step sequences relying upon a silylating or benzoylating reagent for the regioselective protection of M-rich alginic acid, followed by sulfation and deprotection.

Biomacromolecules 24 (6), pp. 2522–2531

Keywords

Sulfated alginates, structural characterization, regioselective sulfation

CNR authors

Gargiulo Valentina

CNR institutes

STEMS – Istituto di Scienze e Tecnologie per l'Energia e la Mobilità Sostenibili