Stable analogues of nojirimycin-synthesis and biological evaluation of nojiristegine and manno-nojiristegine

Agnete H. Viuff; Louise M. Besenbacher; Akiko Kamori; Mikkel T. Jensen; Mogens Kilian; Atsushi Kato; Henrik H. Jensen

doi:10.1039/c5ob01281c

Stable analogues of nojirimycin-synthesis and biological evaluation of nojiristegine and manno-nojiristegine

Agnete H. Viuff, Louise M. Besenbacher, Akiko Kamori, Mikkel T. Jensen, Mogens Kilian, Atsushi Kato, Henrik H. Jensen^*

^*Corresponding author for this work

Hospital Pharmacy

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

17 Scopus citations

Abstract

Two novel iminosugars called nojiristegines, being structural hybrids between nor-tropane alkaloid calystegine and nojirimycins, have been synthesised and found to be stable molecules despite the presence of a hemiaminal functionality. The synthesised iminosugars were evaluated against a panel of glycosidases and the best inhibition (IC₅₀), found against α-glucosidases, was in the micromolar region. The compounds were also evaluated as potential antibiotics but no useful level of activity was observed.

Original language	English
Pages (from-to)	9637-9658
Number of pages	22
Journal	Organic and Biomolecular Chemistry
Volume	13
Issue number	37
DOIs	https://doi.org/10.1039/c5ob01281c
State	Published - 2015/07/14

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Stable analogues of nojirimycin-synthesis and biological evaluation of nojiristegine and manno-nojiristegine",

abstract = "Two novel iminosugars called nojiristegines, being structural hybrids between nor-tropane alkaloid calystegine and nojirimycins, have been synthesised and found to be stable molecules despite the presence of a hemiaminal functionality. The synthesised iminosugars were evaluated against a panel of glycosidases and the best inhibition (IC50), found against α-glucosidases, was in the micromolar region. The compounds were also evaluated as potential antibiotics but no useful level of activity was observed.",

author = "Viuff, {Agnete H.} and Besenbacher, {Louise M.} and Akiko Kamori and Jensen, {Mikkel T.} and Mogens Kilian and Atsushi Kato and Jensen, {Henrik H.}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2015.",

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T1 - Stable analogues of nojirimycin-synthesis and biological evaluation of nojiristegine and manno-nojiristegine

AU - Viuff, Agnete H.

AU - Besenbacher, Louise M.

AU - Kamori, Akiko

AU - Jensen, Mikkel T.

AU - Kilian, Mogens

AU - Kato, Atsushi

AU - Jensen, Henrik H.

PY - 2015/7/14

Y1 - 2015/7/14

N2 - Two novel iminosugars called nojiristegines, being structural hybrids between nor-tropane alkaloid calystegine and nojirimycins, have been synthesised and found to be stable molecules despite the presence of a hemiaminal functionality. The synthesised iminosugars were evaluated against a panel of glycosidases and the best inhibition (IC50), found against α-glucosidases, was in the micromolar region. The compounds were also evaluated as potential antibiotics but no useful level of activity was observed.

AB - Two novel iminosugars called nojiristegines, being structural hybrids between nor-tropane alkaloid calystegine and nojirimycins, have been synthesised and found to be stable molecules despite the presence of a hemiaminal functionality. The synthesised iminosugars were evaluated against a panel of glycosidases and the best inhibition (IC50), found against α-glucosidases, was in the micromolar region. The compounds were also evaluated as potential antibiotics but no useful level of activity was observed.

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U2 - 10.1039/c5ob01281c

DO - 10.1039/c5ob01281c

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SN - 1477-0520

VL - 13

SP - 9637

EP - 9658

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 37

ER -

Stable analogues of nojirimycin-synthesis and biological evaluation of nojiristegine and manno-nojiristegine

Abstract

ASJC Scopus subject areas

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