Synthesis of 1,2- trans -2-Acetamido-2-deoxyhomoiminosugars

Yves Blériot; Anh Tuan Tran; Giuseppe Prencipe; Yerri Jagadeesh; Nicolas Auberger; Sha Zhu; Charles Gauthier; Yongmin Zhang; Jérôme Désiré; Isao Adachi; Atsushi Kato; Matthieu Sollogoub

doi:10.1021/ol502929h

Synthesis of 1,2- trans -2-Acetamido-2-deoxyhomoiminosugars

Yves Blériot^*, Anh Tuan Tran, Giuseppe Prencipe, Yerri Jagadeesh, Nicolas Auberger, Sha Zhu, Charles Gauthier, Yongmin Zhang, Jérôme Désiré, Isao Adachi, Atsushi Kato, Matthieu Sollogoub

^*Corresponding author for this work

Hospital Pharmacy

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

23 Scopus citations

Abstract

The first synthesis of 1,2-trans-homoiminosugars devised as mimics of I-d-GlcNAc and I-d-ManNAc is described. Key steps include a regioselective azidolysis of a cyclic sulfite and a I-amino alcohol skeletal rearrangement applied to a polyhydroxylated azepane. The I-d-GlcNAc derivative has been coupled to serine to deliver an iminosugar C-amino acid. The two homoiminosugars demonstrate moderate glycosidase inhibition.

Original language	English
Pages (from-to)	5516-5519
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	21
DOIs	https://doi.org/10.1021/ol502929h
State	Published - 2014/11/07

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis of 1,2- trans -2-Acetamido-2-deoxyhomoiminosugars",

abstract = "The first synthesis of 1,2-trans-homoiminosugars devised as mimics of I-d-GlcNAc and I-d-ManNAc is described. Key steps include a regioselective azidolysis of a cyclic sulfite and a I-amino alcohol skeletal rearrangement applied to a polyhydroxylated azepane. The I-d-GlcNAc derivative has been coupled to serine to deliver an iminosugar C-amino acid. The two homoiminosugars demonstrate moderate glycosidase inhibition.",

author = "Yves Bl{\'e}riot and Tran, {Anh Tuan} and Giuseppe Prencipe and Yerri Jagadeesh and Nicolas Auberger and Sha Zhu and Charles Gauthier and Yongmin Zhang and J{\'e}r{\^o}me D{\'e}sir{\'e} and Isao Adachi and Atsushi Kato and Matthieu Sollogoub",

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

year = "2014",

month = nov,

day = "7",

doi = "10.1021/ol502929h",

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T1 - Synthesis of 1,2- trans -2-Acetamido-2-deoxyhomoiminosugars

AU - Blériot, Yves

AU - Tran, Anh Tuan

AU - Prencipe, Giuseppe

AU - Jagadeesh, Yerri

AU - Auberger, Nicolas

AU - Zhu, Sha

AU - Gauthier, Charles

AU - Zhang, Yongmin

AU - Désiré, Jérôme

AU - Adachi, Isao

AU - Kato, Atsushi

AU - Sollogoub, Matthieu

PY - 2014/11/7

Y1 - 2014/11/7

N2 - The first synthesis of 1,2-trans-homoiminosugars devised as mimics of I-d-GlcNAc and I-d-ManNAc is described. Key steps include a regioselective azidolysis of a cyclic sulfite and a I-amino alcohol skeletal rearrangement applied to a polyhydroxylated azepane. The I-d-GlcNAc derivative has been coupled to serine to deliver an iminosugar C-amino acid. The two homoiminosugars demonstrate moderate glycosidase inhibition.

AB - The first synthesis of 1,2-trans-homoiminosugars devised as mimics of I-d-GlcNAc and I-d-ManNAc is described. Key steps include a regioselective azidolysis of a cyclic sulfite and a I-amino alcohol skeletal rearrangement applied to a polyhydroxylated azepane. The I-d-GlcNAc derivative has been coupled to serine to deliver an iminosugar C-amino acid. The two homoiminosugars demonstrate moderate glycosidase inhibition.

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U2 - 10.1021/ol502929h

DO - 10.1021/ol502929h

M3 - 学術論文

C2 - 25330462

AN - SCOPUS:84909999552

SN - 1523-7060

VL - 16

SP - 5516

EP - 5519

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Synthesis of 1,2- trans -2-Acetamido-2-deoxyhomoiminosugars

Abstract

ASJC Scopus subject areas

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