Synthesis of pyrrolidine-based analogues of 2-acetamidosugars as N-acetyl-d-glucosaminidase inhibitors

Anh Tuan Tran; Bo Luo; Yerri Jagadeesh; Nicolas Auberger; Jérôme Désiré; Shinpei Nakagawa; Atsushi Kato; Yongmin Zhang; Yves Blériot; Matthieu Sollogoub

doi:10.1016/j.carres.2015.02.014

Synthesis of pyrrolidine-based analogues of 2-acetamidosugars as N-acetyl-d-glucosaminidase inhibitors

Anh Tuan Tran, Bo Luo, Yerri Jagadeesh, Nicolas Auberger, Jérôme Désiré, Shinpei Nakagawa, Atsushi Kato, Yongmin Zhang, Yves Blériot, Matthieu Sollogoub^*

^*Corresponding author for this work

Hospital Pharmacy

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

7 Scopus citations

Abstract

A ring-contraction strategy applied to β-azido,γ-hydroxyazepanes yielded after functional group manipulation new tetrahydroxylated pyrrolidines displaying an acetamido moiety, one of these iminosugars demonstrating low micromolar inhibition on N-acetylglucosaminidases.

Original language	English
Pages (from-to)	56-62
Number of pages	7
Journal	Carbohydrate Research
Volume	409
DOIs	https://doi.org/10.1016/j.carres.2015.02.014
State	Published - 2015/05/29

Keywords

Glycosidase inhibitors
Iminosugars
Pyrrolidines
Ring-contraction

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

Access to Document

10.1016/j.carres.2015.02.014

Cite this

@article{2798043a3ce24ccd8704638adb9b54e3,

title = "Synthesis of pyrrolidine-based analogues of 2-acetamidosugars as N-acetyl-d-glucosaminidase inhibitors",

abstract = "A ring-contraction strategy applied to β-azido,γ-hydroxyazepanes yielded after functional group manipulation new tetrahydroxylated pyrrolidines displaying an acetamido moiety, one of these iminosugars demonstrating low micromolar inhibition on N-acetylglucosaminidases.",

keywords = "Glycosidase inhibitors, Iminosugars, Pyrrolidines, Ring-contraction",

author = "Tran, {Anh Tuan} and Bo Luo and Yerri Jagadeesh and Nicolas Auberger and J{\'e}r{\^o}me D{\'e}sir{\'e} and Shinpei Nakagawa and Atsushi Kato and Yongmin Zhang and Yves Bl{\'e}riot and Matthieu Sollogoub",

year = "2015",

month = may,

day = "29",

doi = "10.1016/j.carres.2015.02.014",

language = "英語",

volume = "409",

pages = "56--62",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier Ltd.",

}

TY - JOUR

T1 - Synthesis of pyrrolidine-based analogues of 2-acetamidosugars as N-acetyl-d-glucosaminidase inhibitors

AU - Tran, Anh Tuan

AU - Luo, Bo

AU - Jagadeesh, Yerri

AU - Auberger, Nicolas

AU - Désiré, Jérôme

AU - Nakagawa, Shinpei

AU - Kato, Atsushi

AU - Zhang, Yongmin

AU - Blériot, Yves

AU - Sollogoub, Matthieu

PY - 2015/5/29

Y1 - 2015/5/29

N2 - A ring-contraction strategy applied to β-azido,γ-hydroxyazepanes yielded after functional group manipulation new tetrahydroxylated pyrrolidines displaying an acetamido moiety, one of these iminosugars demonstrating low micromolar inhibition on N-acetylglucosaminidases.

AB - A ring-contraction strategy applied to β-azido,γ-hydroxyazepanes yielded after functional group manipulation new tetrahydroxylated pyrrolidines displaying an acetamido moiety, one of these iminosugars demonstrating low micromolar inhibition on N-acetylglucosaminidases.

KW - Glycosidase inhibitors

KW - Iminosugars

KW - Pyrrolidines

KW - Ring-contraction

UR - http://www.scopus.com/inward/record.url?scp=84928777995&partnerID=8YFLogxK

U2 - 10.1016/j.carres.2015.02.014

DO - 10.1016/j.carres.2015.02.014

M3 - 学術論文

C2 - 25950121

AN - SCOPUS:84928777995

SN - 0008-6215

VL - 409

SP - 56

EP - 62

JO - Carbohydrate Research

JF - Carbohydrate Research

ER -

Synthesis of pyrrolidine-based analogues of 2-acetamidosugars as N-acetyl-d-glucosaminidase inhibitors

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this