Issue 9, 2011
From the journal:

Organic & Biomolecular Chemistry

l-DMDP, l-homoDMDP and their C-3 fluorinated derivatives: synthesis and glycosidase-inhibition†

Yi-Xian Li,ae   Mu-Hua Huang,a   Yukiko Yamashita,b   Atsushi Kato,b   Yue-Mei Jia,a   Wu-Bao Wang,a   George W. J. Fleet,c   Robert J. Nashd  and  Chu-Yi Yu*a  

* 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, China
E-mail: yucy@iccas.ac.cn

b Department of Hospital Pharmacy, University of Toyama, Sugitani, Toyama, Japan

c Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, UK

d Phytoquest Limited, IBERS, Plas Gogerddan, Aberystwyth, Ceredigion, Wales, UK

e Graduate University of The Chinese Academy of Sciences, Beijing, China

Abstract

L-DMDP and L-homoDMDP, the enantiomers of naturally occurring DMDP and homoDMDP have been synthesized from D-xylose derived cyclic nitrone 9. Their 3-deoxy-3-fluorinated analogues were also obtained from polyhydroxylated fluorinated cyclic nitrone 10, which was prepared from fluorinated sugar 12 in seven steps. Bioactivities of these iminosugars against various glycosidases were evaluated. While L-DMDP and L-homoDMDP are potent inhibitors of α-glucosidases, a sharp decrease of inhibition was found when the C-3 hydroxyl group of these compounds was replaced by fluoride, which showed the great importance of the C-3 hydroxyl in their interaction with enzymes.

Graphical abstract: l-DMDP, l-homoDMDP and their C-3 fluorinated derivatives: synthesis and glycosidase-inhibition

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Article information

DOI
https://doi.org/10.1039/C0OB01063D
Article type
Paper
Submitted
23 Nov 2010
Accepted
08 Feb 2011
First published
18 Mar 2011

Org. Biomol. Chem., 2011,9, 3405-3414

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L-DMDP, L-homoDMDP and their C-3 fluorinated derivatives: synthesis and glycosidase-inhibition

Y. Li, M. Huang, Y. Yamashita, A. Kato, Y. Jia, W. Wang, G. W. J. Fleet, R. J. Nash and C. Yu, Org. Biomol. Chem., 2011, 9, 3405 DOI: 10.1039/C0OB01063D

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