Synthesis of 1,2-cis -homoiminosugars derived from GlcNAc and GaLNAc exploiting a β-amino alcohol skeletal rearrangement

Yves Blériot; Nicolas Auberger; Yerri Jagadeesh; Charles Gauthier; Giuseppe Prencipe; Anh Tuan Tran; Jérôme Marrot; Jérôme Désiré; Arisa Yamamoto; Atsushi Kato; Matthieu Sollogoub

doi:10.1021/ol502926f

Synthesis of 1,2-cis -homoiminosugars derived from GlcNAc and GaLNAc exploiting a β-amino alcohol skeletal rearrangement

Yves Blériot^*, Nicolas Auberger, Yerri Jagadeesh, Charles Gauthier, Giuseppe Prencipe, Anh Tuan Tran, Jérôme Marrot, Jérôme Désiré, Arisa Yamamoto, Atsushi Kato, Matthieu Sollogoub

^*Corresponding author for this work

Hospital Pharmacy

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

33 Scopus citations

Abstract

The synthesis of 1,2-cis-homoiminosugars bearing an NHAc group at the C-2 position is described. The key step to prepare these α-d-GlcNAc and α-d-GalNAc mimics utilizes a β-amino alcohol skeletal rearrangement applied to an azepane precursor. This strategy also allows access to naturally occurring α-HGJ and α-HNJ. The α-d-GlcNAc-configured iminosugar was coupled to a glucoside acceptor to yield a novel pseudodisaccharide. Preliminary glycosidase inhibition evaluation indicates that the α-d-GalNAc-configured homoiminosugar is a potent and selective α-N-acetylgalactosaminidase inhibitor.

Original language	English
Pages (from-to)	5512-5515
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	21
DOIs	https://doi.org/10.1021/ol502926f
State	Published - 2014/11/07

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol502926f

Cite this

@article{d94024b00c21418dba89fb3c458b10ab,

title = "Synthesis of 1,2-cis -homoiminosugars derived from GlcNAc and GaLNAc exploiting a β-amino alcohol skeletal rearrangement",

abstract = "The synthesis of 1,2-cis-homoiminosugars bearing an NHAc group at the C-2 position is described. The key step to prepare these α-d-GlcNAc and α-d-GalNAc mimics utilizes a β-amino alcohol skeletal rearrangement applied to an azepane precursor. This strategy also allows access to naturally occurring α-HGJ and α-HNJ. The α-d-GlcNAc-configured iminosugar was coupled to a glucoside acceptor to yield a novel pseudodisaccharide. Preliminary glycosidase inhibition evaluation indicates that the α-d-GalNAc-configured homoiminosugar is a potent and selective α-N-acetylgalactosaminidase inhibitor.",

author = "Yves Bl{\'e}riot and Nicolas Auberger and Yerri Jagadeesh and Charles Gauthier and Giuseppe Prencipe and Tran, {Anh Tuan} and J{\'e}r{\^o}me Marrot and J{\'e}r{\^o}me D{\'e}sir{\'e} and Arisa Yamamoto and Atsushi Kato and Matthieu Sollogoub",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

month = nov,

day = "7",

doi = "10.1021/ol502926f",

language = "英語",

volume = "16",

pages = "5512--5515",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Synthesis of 1,2-cis -homoiminosugars derived from GlcNAc and GaLNAc exploiting a β-amino alcohol skeletal rearrangement

AU - Blériot, Yves

AU - Auberger, Nicolas

AU - Jagadeesh, Yerri

AU - Gauthier, Charles

AU - Prencipe, Giuseppe

AU - Tran, Anh Tuan

AU - Marrot, Jérôme

AU - Désiré, Jérôme

AU - Yamamoto, Arisa

AU - Kato, Atsushi

AU - Sollogoub, Matthieu

PY - 2014/11/7

Y1 - 2014/11/7

N2 - The synthesis of 1,2-cis-homoiminosugars bearing an NHAc group at the C-2 position is described. The key step to prepare these α-d-GlcNAc and α-d-GalNAc mimics utilizes a β-amino alcohol skeletal rearrangement applied to an azepane precursor. This strategy also allows access to naturally occurring α-HGJ and α-HNJ. The α-d-GlcNAc-configured iminosugar was coupled to a glucoside acceptor to yield a novel pseudodisaccharide. Preliminary glycosidase inhibition evaluation indicates that the α-d-GalNAc-configured homoiminosugar is a potent and selective α-N-acetylgalactosaminidase inhibitor.

AB - The synthesis of 1,2-cis-homoiminosugars bearing an NHAc group at the C-2 position is described. The key step to prepare these α-d-GlcNAc and α-d-GalNAc mimics utilizes a β-amino alcohol skeletal rearrangement applied to an azepane precursor. This strategy also allows access to naturally occurring α-HGJ and α-HNJ. The α-d-GlcNAc-configured iminosugar was coupled to a glucoside acceptor to yield a novel pseudodisaccharide. Preliminary glycosidase inhibition evaluation indicates that the α-d-GalNAc-configured homoiminosugar is a potent and selective α-N-acetylgalactosaminidase inhibitor.

UR - http://www.scopus.com/inward/record.url?scp=84910002429&partnerID=8YFLogxK

U2 - 10.1021/ol502926f

DO - 10.1021/ol502926f

M3 - 学術論文

C2 - 25330411

AN - SCOPUS:84910002429

SN - 1523-7060

VL - 16

SP - 5512

EP - 5515

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Synthesis of 1,2-cis -homoiminosugars derived from GlcNAc and GaLNAc exploiting a β-amino alcohol skeletal rearrangement

Abstract

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this