Stereocomplementary synthesis of casuarine and its 6- epi -, 7- epi -, and 6,7-di epi -stereoisomers

Stereocomplementary synthesis of casuarine and its 6- epi -, 7- epi -, and 6,7-di epi -stereoisomers

Four diastereomers belonging to the family of casuarines, including casuarine (1), 6- -casuarine (2), 7- -casuarine (13) and 6,7-di -casuarine (14), have been synthesized from D-arabinose-derived cyclic nitrone 7 and nitrone-derived aldehyde 4 by a stereocomplementary strategy. Glycosidase inhibitio...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic & biomolecular chemistry 2021-11, Vol.19 (43), p.9410-9420
Hauptverfasser: Li, Yi-Xian, Wang, Jun-Zhe, Kato, Atsushi, Shimadate, Yuna, Kise, Maki, Jia, Yue-Mei, Fleet, George W J, Yu, Chu-Yi
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Four diastereomers belonging to the family of casuarines, including casuarine (1), 6- -casuarine (2), 7- -casuarine (13) and 6,7-di -casuarine (14), have been synthesized from D-arabinose-derived cyclic nitrone 7 and nitrone-derived aldehyde 4 by a stereocomplementary strategy. Glycosidase inhibition comparison showed that 6- -casuarine (2) exhibits enhanced inhibition of trehalase (IC = 9.7 μM) and 6,7-di -casuarine (14) leads to specific inhibition of trehalase.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob01725j