Synthesis of pyrrolidine-based analogues of 2-acetamidosugars as N-acetyl-d-glucosaminidase inhibitors. (29th May 2015)

• Record Type: Journal Article
• Authors: Tran, Anh Tuan; Luo, Bo; Jagadeesh, Yerri; Auberger, Nicolas; Désiré, Jérôme; Nakagawa, Shinpei; Kato, Atsushi; Zhang, Yongmin; Blériot, Yves; Sollogoub, Matthieu
• Is Part Of: Carbohydrate research. Volume 409(2015)
• Page Start: 56
• Page End: 62
• Publication Date: 2015-05-29
• Subjects: Iminosugars -- Ring-contraction -- Glycosidase inhibitors -- Pyrrolidines; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2015.02.014
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: A ring-contraction strategy applied to β-azido, γ-hydroxyazepanes yielded after functional group manipulation new tetrahydroxylated pyrrolidines displaying an acetamido moiety, one of these iminosugars demonstrating low micromolar inhibition on N-acetylglucosaminidases. Graphical abstract: Highlights: A new family of amino-functionalised pyrolidines was synthesized. A ring-contraction of β-azido, γ-hydroxyazepanes was used. A low micromolar inhibitor of β-N-acetylehexosaminidase identified.