synthesis of natural o-linked carba-disaccharides, (+)- and (−)-pericosine e, and their analogues as α-glucosidase inhibitors
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ID: 183806
2017
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Abstract
Pericosine E (6), a metabolite of Periconia byssoides OUPS-N133 was originally isolated from the sea hare Aplysia kurodai, which exists as an enantiomeric mixture in nature. The enantiospecific syntheses of both enantiomers of Periconia byssoides OUPS-N133 has been achieved, along with six stereoisomers, using a common simple synthetic strategy. For these efficient syntheses, highly regio- and steroselective processes for the preparation of bromohydrin and anti-epoxide intermediates were applied. In order to access the unique O-linked carbadisaccharide structure, coupling of chlorohydrin as a donor and anti-epoxide as an acceptor was achieved using catalytic BF3·Et2O. Most of the synthesized compounds exhibited selectively significant inhibitory activity against α-glycosidase derived from yeast. The strongest analog showed almost 50 times the activity of the positive control, deoxynojirimycin.
| Reference Key |
usami2017marinesynthesis
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|---|---|
| Authors | ;Yoshihide Usami;Koji Mizuki;Rikiya Kawahata;Makio Shibano;Atsuko Sekine;Hiroki Yoneyama;Shinya Harusawa |
| Journal | jixie gongcheng xuebao/journal of mechanical engineering |
| Year | 2017 |
| DOI |
10.3390/md15010022
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| URL | |
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