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

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

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

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Veröffentlicht in:Organic & biomolecular chemistry 2021-11, Vol.19 (43), p.9410-9420
Hauptverfasser: Yi-Xian, Li, Jun-Zhe, Wang, Kato, Atsushi, Shimadate, Yuna, Kise, Maki, Yue-Mei, Jia, Fleet, George W J, Chu-Yi, Yu
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes
Arabinose
Diastereoisomers
Glycosidases
Stereoisomerism
Stereoisomers
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Zusammenfassung:Four diastereomers belonging to the family of casuarines, including casuarine (1), 6-epi-casuarine (2), 7-epi-casuarine (13) and 6,7-diepi-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-epi-casuarine (2) exhibits enhanced inhibition of trehalase (IC50 = 9.7 μM) and 6,7-diepi-casuarine (14) leads to specific inhibition of trehalase.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob01725j