Issue 43, 2021
From the journal:

Organic & Biomolecular Chemistry

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

Yi-Xian Li,ab   Jun-Zhe Wang,ab   Atsushi Kato, ORCID logo *c   Yuna Shimadate,c   Maki Kise,c   Yue-Mei Jia,ab   George W. J. Fleetd  and  Chu-Yi Yu ORCID logo *ab  

* Corresponding authors

a Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
E-mail: yucy@iccas.ac.cn

b University of Chinese Academy of Sciences, Beijing 100049, China

c Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
E-mail: kato@med.u-toyama.ac.jp

d Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK

Abstract

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.

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

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/D1OB01725J
Article type
Paper
Submitted
02 ก.ย. 2564
Accepted
10 ต.ค. 2564
First published
12 ต.ค. 2564

Org. Biomol. Chem., 2021,19, 9410-9420

Permissions

Request permissions

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

Y. Li, J. Wang, A. Kato, Y. Shimadate, M. Kise, Y. Jia, G. W. J. Fleet and C. Yu, Org. Biomol. Chem., 2021, 19, 9410 DOI: 10.1039/D1OB01725J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements