Novel 3,4-disubstituted-Neu5Ac2en derivatives as probes to investigate flexibility of the influenza virus sialidase 150-loop.
Identifieur interne : 000923 ( Ncbi/Checkpoint ); précédent : 000922; suivant : 000924Novel 3,4-disubstituted-Neu5Ac2en derivatives as probes to investigate flexibility of the influenza virus sialidase 150-loop.
Auteurs : Santosh Rudrawar [Australie] ; Jeffrey C. Dyason ; Andrea Maggioni ; Robin J. Thomson ; Mark Von ItzsteinSource :
- Bioorganic & medicinal chemistry [ 1464-3391 ] ; 2013.
Descripteurs français
- KwdFr :
- MESH :
- analogues et dérivés : Acide N-acétyl-neuraminique.
- enzymologie : Orthomyxoviridae.
- métabolisme : Acide N-acétyl-neuraminique, Sialidase.
- Acide N-acétyl-neuraminique, Acides sialiques, Liaison aux protéines, Sialidase, Sondes moléculaires, Structure secondaire des protéines.
English descriptors
- KwdEn :
- Molecular Probes, N-Acetylneuraminic Acid (analogs & derivatives), N-Acetylneuraminic Acid (chemistry), N-Acetylneuraminic Acid (metabolism), Neuraminidase (chemistry), Neuraminidase (metabolism), Orthomyxoviridae (enzymology), Protein Binding, Protein Structure, Secondary, Sialic Acids (chemistry).
- MESH :
- chemical , analogs & derivatives : N-Acetylneuraminic Acid.
- chemical , chemistry : N-Acetylneuraminic Acid, Neuraminidase, Sialic Acids.
- chemical , metabolism : N-Acetylneuraminic Acid, Neuraminidase.
- chemical : Molecular Probes.
- enzymology : Orthomyxoviridae.
- Protein Binding, Protein Structure, Secondary.
Abstract
Novel 3,4-disubstituted-Neu5Ac2en derivatives have been synthesised to probe the open 150-loop conformation of influenza virus sialidases. Both equatorially and axially (epi) substituted C4 amino and guanidino 3-(p-tolyl)allyl-Neu5Ac2en derivatives were prepared, via the 4-epi-hydroxy derivative. The equatorially-substituted 4-amino derivative showed low micromolar inhibition of both group-1 (pdm09 H1N1) and group-2 (pdm57 H2N2) sialidases, and provides the first in vitro evidence that a group-2 sialidase may exhibit 150-loop flexibility.
DOI: 10.1016/j.bmc.2013.05.054
PubMed: 23800724
Affiliations:
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pubmed:23800724Le document en format XML
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<term>N-Acetylneuraminic Acid (metabolism)</term>
<term>Neuraminidase (chemistry)</term>
<term>Neuraminidase (metabolism)</term>
<term>Orthomyxoviridae (enzymology)</term>
<term>Protein Binding</term>
<term>Protein Structure, Secondary</term>
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<term>Acides sialiques ()</term>
<term>Liaison aux protéines</term>
<term>Orthomyxoviridae (enzymologie)</term>
<term>Sialidase ()</term>
<term>Sialidase (métabolisme)</term>
<term>Sondes moléculaires</term>
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<term>Acides sialiques</term>
<term>Liaison aux protéines</term>
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<term>Sondes moléculaires</term>
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<front><div type="abstract" xml:lang="en">Novel 3,4-disubstituted-Neu5Ac2en derivatives have been synthesised to probe the open 150-loop conformation of influenza virus sialidases. Both equatorially and axially (epi) substituted C4 amino and guanidino 3-(p-tolyl)allyl-Neu5Ac2en derivatives were prepared, via the 4-epi-hydroxy derivative. The equatorially-substituted 4-amino derivative showed low micromolar inhibition of both group-1 (pdm09 H1N1) and group-2 (pdm57 H2N2) sialidases, and provides the first in vitro evidence that a group-2 sialidase may exhibit 150-loop flexibility. </div>
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<name sortKey="Maggioni, Andrea" sort="Maggioni, Andrea" uniqKey="Maggioni A" first="Andrea" last="Maggioni">Andrea Maggioni</name>
<name sortKey="Thomson, Robin J" sort="Thomson, Robin J" uniqKey="Thomson R" first="Robin J" last="Thomson">Robin J. Thomson</name>
<name sortKey="Von Itzstein, Mark" sort="Von Itzstein, Mark" uniqKey="Von Itzstein M" first="Mark" last="Von Itzstein">Mark Von Itzstein</name>
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<country name="Australie"><noRegion><name sortKey="Rudrawar, Santosh" sort="Rudrawar, Santosh" uniqKey="Rudrawar S" first="Santosh" last="Rudrawar">Santosh Rudrawar</name>
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