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Mar. Drugs 2017, 15(1), 22; doi:10.3390/md15010022

Synthesis of Natural O-Linked Carba-Disaccharides, (+)- and (−)-Pericosine E, and Their Analogues as α-Glucosidase Inhibitors

1
Laboratory of Pharmaceutical Organic Chemistry, Osaka University of Pharmaceutical Sciences, Nasahara 4-20-1, Takatsuki, Osaka 569-1094, Japan
2
Laboratory of Pharmacognosy, Osaka University of Pharmaceutical Sciences, Nasahara 4-20-1, Takatsuki, Osaka 569-1094, Japan
*
Author to whom correspondence should be addressed.
Academic Editor: Vassilios Roussis
Received: 15 December 2016 / Revised: 12 January 2017 / Accepted: 16 January 2017 / Published: 23 January 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. View Full-Text
Keywords: synthesis; pericosine E; marine natural product; O-linked carba-disaccharide; α-glucosidase inhibitor; enantiomeric mixture synthesis; pericosine E; marine natural product; O-linked carba-disaccharide; α-glucosidase inhibitor; enantiomeric mixture
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Usami, Y.; Mizuki, K.; Kawahata, R.; Shibano, M.; Sekine, A.; Yoneyama, H.; Harusawa, S. Synthesis of Natural O-Linked Carba-Disaccharides, (+)- and (−)-Pericosine E, and Their Analogues as α-Glucosidase Inhibitors. Mar. Drugs 2017, 15, 22.

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