Synthesis and glycosidase inhibition of Australine and its fluorinated derivatives

Yi Xian Li; Yousuke Shimada; Kasumi Sato; Atsushi Kato; Wei Zhang; Yue Mei Jia; George W.J. Fleet; Min Xiao; Chu Yi Yu

doi:10.1021/ol503728e

Synthesis and glycosidase inhibition of Australine and its fluorinated derivatives

Yi Xian Li, Yousuke Shimada, Kasumi Sato, Atsushi Kato^*, Wei Zhang, Yue Mei Jia, George W.J. Fleet, Min Xiao, Chu Yi Yu

^*Corresponding author for this work

Hospital Pharmacy

Research output: Contribution to journal › Article › peer-review

45 Scopus citations

Abstract

Australine (1), 7-epi-australine (2), and their C-7-fluorinated derivatives 4 and 5 have been synthesized efficiently from d-arabinose-derived cyclic nitrone 11. Fluorination at the C-7 position enhanced the inhibition against A. niger α-glucosidase, and this constitutes the first example of fluorination substitution for a hydroxyl increasing the inhibition of any glycosidases. The enantiomers synthesized from nitrone ent-11 showed no inhibition of the corresponding enzymes.

Original language	English
Pages (from-to)	716-719
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	3
DOIs	https://doi.org/10.1021/ol503728e
State	Published - 2015/02/06

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol503728e

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title = "Synthesis and glycosidase inhibition of Australine and its fluorinated derivatives",

abstract = "Australine (1), 7-epi-australine (2), and their C-7-fluorinated derivatives 4 and 5 have been synthesized efficiently from d-arabinose-derived cyclic nitrone 11. Fluorination at the C-7 position enhanced the inhibition against A. niger α-glucosidase, and this constitutes the first example of fluorination substitution for a hydroxyl increasing the inhibition of any glycosidases. The enantiomers synthesized from nitrone ent-11 showed no inhibition of the corresponding enzymes.",

author = "Li, {Yi Xian} and Yousuke Shimada and Kasumi Sato and Atsushi Kato and Wei Zhang and Jia, {Yue Mei} and Fleet, {George W.J.} and Min Xiao and Yu, {Chu Yi}",

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T1 - Synthesis and glycosidase inhibition of Australine and its fluorinated derivatives

AU - Li, Yi Xian

AU - Shimada, Yousuke

AU - Sato, Kasumi

AU - Kato, Atsushi

AU - Zhang, Wei

AU - Jia, Yue Mei

AU - Fleet, George W.J.

AU - Xiao, Min

AU - Yu, Chu Yi

PY - 2015/2/6

Y1 - 2015/2/6

N2 - Australine (1), 7-epi-australine (2), and their C-7-fluorinated derivatives 4 and 5 have been synthesized efficiently from d-arabinose-derived cyclic nitrone 11. Fluorination at the C-7 position enhanced the inhibition against A. niger α-glucosidase, and this constitutes the first example of fluorination substitution for a hydroxyl increasing the inhibition of any glycosidases. The enantiomers synthesized from nitrone ent-11 showed no inhibition of the corresponding enzymes.

AB - Australine (1), 7-epi-australine (2), and their C-7-fluorinated derivatives 4 and 5 have been synthesized efficiently from d-arabinose-derived cyclic nitrone 11. Fluorination at the C-7 position enhanced the inhibition against A. niger α-glucosidase, and this constitutes the first example of fluorination substitution for a hydroxyl increasing the inhibition of any glycosidases. The enantiomers synthesized from nitrone ent-11 showed no inhibition of the corresponding enzymes.

UR - http://www.scopus.com/inward/record.url?scp=84922602756&partnerID=8YFLogxK

U2 - 10.1021/ol503728e

DO - 10.1021/ol503728e

M3 - 学術論文

C2 - 25621897

AN - SCOPUS:84922602756

SN - 1523-7060

VL - 17

SP - 716

EP - 719

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Synthesis and glycosidase inhibition of Australine and its fluorinated derivatives

Abstract

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