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Evaluation of peptide-aldehyde inhibitors using R188I mutant of SARS 3CL protease as a proteolysis-resistant mutant

Identifieur interne : 000751 ( PascalFrancis/Curation ); précédent : 000750; suivant : 000752

Evaluation of peptide-aldehyde inhibitors using R188I mutant of SARS 3CL protease as a proteolysis-resistant mutant

Auteurs : Kenichi Akaji [Japon] ; Hiroyuki Konno [Japon] ; Mari Onozuka [Japon] ; Ayumi Makino [Japon] ; Hiroyuki Saito [Japon] ; Kazuto Nosaka [Japon]

Source :

RBID : Pascal:09-0041831

Descripteurs français

English descriptors

Abstract

The 3C-like (3CL) protease of the severe acute respiratory syndrome (SARS) coronavirus is a key enzyme for the virus maturation. We found for the first time that the mature SARS 3CL protease is subject to degradation at 188Arg/189Gln. Replacing Arg with lle at position 188 rendered the protease resistant to proteolysis. The R188I mutant digested a conserved undecapeptide substrate with a Km of 33.8 μM and kcat of 4753 s-1. Compared with the value reported for the mature protease containing a C-terminal His-tag, the relative activity of the mutant was nearly 106. Novel peptide-aldehyde derivatives containing a side-chain-protected C-terminal Gln efficiently inhibited the catalytic activity of the R188I mutant. The results indicated for the first time that the tetrapeptide sequence is enough for inhibitory activities of peptide-aldehyde derivatives.
pA  
A01 01  1    @0 0968-0896
A03   1    @0 Bioorg. med. chem.
A05       @2 16
A06       @2 21
A08 01  1  ENG  @1 Evaluation of peptide-aldehyde inhibitors using R188I mutant of SARS 3CL protease as a proteolysis-resistant mutant
A11 01  1    @1 AKAJI (Kenichi)
A11 02  1    @1 KONNO (Hiroyuki)
A11 03  1    @1 ONOZUKA (Mari)
A11 04  1    @1 MAKINO (Ayumi)
A11 05  1    @1 SAITO (Hiroyuki)
A11 06  1    @1 NOSAKA (Kazuto)
A14 01      @1 Department of Chemistry, Graduate School of Medical Science, Kyoto Prefectural University of Medicine @2 Kita-ku, Kyoto 603-8334 @3 JPN @Z 1 aut. @Z 2 aut. @Z 3 aut. @Z 6 aut.
A14 02      @1 Department of Biophysical Chemistry, Kobe Pharmaceutical University @2 Kobe 658-8558 @3 JPN @Z 4 aut. @Z 5 aut.
A20       @1 9400-9408
A21       @1 2008
A23 01      @0 ENG
A43 01      @1 INIST @2 26564 @5 354000185936900010
A44       @0 0000 @1 © 2009 INIST-CNRS. All rights reserved.
A47 01  1    @0 09-0041831
A60       @1 P
A61       @0 A
A64 01  1    @0 Bioorganic & medicinal chemistry
A66 01      @0 GBR
A99       @0 1/2 p.ref. et notes
C01 01    ENG  @0 The 3C-like (3CL) protease of the severe acute respiratory syndrome (SARS) coronavirus is a key enzyme for the virus maturation. We found for the first time that the mature SARS 3CL protease is subject to degradation at 188Arg/189Gln. Replacing Arg with lle at position 188 rendered the protease resistant to proteolysis. The R188I mutant digested a conserved undecapeptide substrate with a Km of 33.8 μM and kcat of 4753 s-1. Compared with the value reported for the mature protease containing a C-terminal His-tag, the relative activity of the mutant was nearly 106. Novel peptide-aldehyde derivatives containing a side-chain-protected C-terminal Gln efficiently inhibited the catalytic activity of the R188I mutant. The results indicated for the first time that the tetrapeptide sequence is enough for inhibitory activities of peptide-aldehyde derivatives.
C02 01  X    @0 002B02S05
C03 01  X  FRE  @0 Peptide @5 01
C03 01  X  ENG  @0 Peptides @5 01
C03 01  X  SPA  @0 Péptido @5 01
C03 02  X  FRE  @0 Aldéhyde @5 02
C03 02  X  ENG  @0 Aldehyde @5 02
C03 02  X  SPA  @0 Aldehído @5 02
C03 03  X  FRE  @0 Inhibiteur protease @2 FR @5 03
C03 03  X  ENG  @0 Protease inhibitor @2 FR @5 03
C03 03  X  SPA  @0 Inhibidor proteasa @2 FR @5 03
C03 04  X  FRE  @0 Mutation @5 04
C03 04  X  ENG  @0 Mutation @5 04
C03 04  X  SPA  @0 Mutación @5 04
C03 05  X  FRE  @0 Cysteine endopeptidases @2 FE @5 05
C03 05  X  ENG  @0 Cysteine endopeptidases @2 FE @5 05
C03 05  X  SPA  @0 Cysteine endopeptidases @2 FE @5 05
C03 06  X  FRE  @0 Virus syndrome respiratoire aigu sévère @2 NW @5 07
C03 06  X  ENG  @0 Severe acute respiratory syndrome virus @2 NW @5 07
C03 06  X  SPA  @0 Severe acute respiratory syndrome virus @2 NW @5 07
C03 07  X  FRE  @0 Résistance hydrolyse @5 08
C03 07  X  ENG  @0 Hydrolysis resistance @5 08
C03 07  X  SPA  @0 Resistencia hidrólisis @5 08
C03 08  X  FRE  @0 Activité biologique @5 09
C03 08  X  ENG  @0 Biological activity @5 09
C03 08  X  SPA  @0 Actividad biológica @5 09
C03 09  X  FRE  @0 Synthèse chimique @5 10
C03 09  X  ENG  @0 Chemical synthesis @5 10
C03 09  X  SPA  @0 Síntesis química @5 10
C03 10  X  FRE  @0 Synthèse peptidique @5 11
C03 10  X  ENG  @0 Peptide synthesis @5 11
C03 10  X  SPA  @0 Síntesis peptídica @5 11
C03 11  X  FRE  @0 In vitro @5 12
C03 11  X  ENG  @0 In vitro @5 12
C03 11  X  SPA  @0 In vitro @5 12
C03 12  X  FRE  @0 Inhibiteur enzyme @5 32
C03 12  X  ENG  @0 Enzyme inhibitor @5 32
C03 12  X  SPA  @0 Inhibidor enzima @5 32
C03 13  X  FRE  @0 Glutamique acide(acétylthréonyl-séryl-alanyl-valyl-leucyl-1-désoxy) @4 INC @5 76
C07 01  X  FRE  @0 Peptidases @2 FE
C07 01  X  ENG  @0 Peptidases @2 FE
C07 01  X  SPA  @0 Peptidases @2 FE
C07 02  X  FRE  @0 Hydrolases @2 FE
C07 02  X  ENG  @0 Hydrolases @2 FE
C07 02  X  SPA  @0 Hydrolases @2 FE
C07 03  X  FRE  @0 Enzyme @2 FE
C07 03  X  ENG  @0 Enzyme @2 FE
C07 03  X  SPA  @0 Enzima @2 FE
C07 04  X  FRE  @0 Coronavirus @2 NW
C07 04  X  ENG  @0 Coronavirus @2 NW
C07 04  X  SPA  @0 Coronavirus @2 NW
C07 05  X  FRE  @0 Coronaviridae @2 NW
C07 05  X  ENG  @0 Coronaviridae @2 NW
C07 05  X  SPA  @0 Coronaviridae @2 NW
C07 06  X  FRE  @0 Nidovirales @2 NW
C07 06  X  ENG  @0 Nidovirales @2 NW
C07 06  X  SPA  @0 Nidovirales @2 NW
C07 07  X  FRE  @0 Virus @2 NW
C07 07  X  ENG  @0 Virus @2 NW
C07 07  X  SPA  @0 Virus @2 NW
N21       @1 026

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Pascal:09-0041831

Le document en format XML

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<term>Enzyme inhibitor</term>
<term>Hydrolysis resistance</term>
<term>In vitro</term>
<term>Mutation</term>
<term>Peptide synthesis</term>
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<div type="abstract" xml:lang="en">The 3C-like (3CL) protease of the severe acute respiratory syndrome (SARS) coronavirus is a key enzyme for the virus maturation. We found for the first time that the mature SARS 3CL protease is subject to degradation at 188Arg/189Gln. Replacing Arg with lle at position 188 rendered the protease resistant to proteolysis. The R188I mutant digested a conserved undecapeptide substrate with a K
<sub>m</sub>
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<s0>The 3C-like (3CL) protease of the severe acute respiratory syndrome (SARS) coronavirus is a key enzyme for the virus maturation. We found for the first time that the mature SARS 3CL protease is subject to degradation at 188Arg/189Gln. Replacing Arg with lle at position 188 rendered the protease resistant to proteolysis. The R188I mutant digested a conserved undecapeptide substrate with a K
<sub>m</sub>
of 33.8 μM and k
<sub>cat</sub>
of 4753 s
<sup>-1</sup>
. Compared with the value reported for the mature protease containing a C-terminal His-tag, the relative activity of the mutant was nearly 10
<sup>6</sup>
. Novel peptide-aldehyde derivatives containing a side-chain-protected C-terminal Gln efficiently inhibited the catalytic activity of the R188I mutant. The results indicated for the first time that the tetrapeptide sequence is enough for inhibitory activities of peptide-aldehyde derivatives.</s0>
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<s0>Mutation</s0>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="ENG">
<s0>Mutation</s0>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="SPA">
<s0>Mutación</s0>
<s5>04</s5>
</fC03>
<fC03 i1="05" i2="X" l="FRE">
<s0>Cysteine endopeptidases</s0>
<s2>FE</s2>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="ENG">
<s0>Cysteine endopeptidases</s0>
<s2>FE</s2>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="SPA">
<s0>Cysteine endopeptidases</s0>
<s2>FE</s2>
<s5>05</s5>
</fC03>
<fC03 i1="06" i2="X" l="FRE">
<s0>Virus syndrome respiratoire aigu sévère</s0>
<s2>NW</s2>
<s5>07</s5>
</fC03>
<fC03 i1="06" i2="X" l="ENG">
<s0>Severe acute respiratory syndrome virus</s0>
<s2>NW</s2>
<s5>07</s5>
</fC03>
<fC03 i1="06" i2="X" l="SPA">
<s0>Severe acute respiratory syndrome virus</s0>
<s2>NW</s2>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="FRE">
<s0>Résistance hydrolyse</s0>
<s5>08</s5>
</fC03>
<fC03 i1="07" i2="X" l="ENG">
<s0>Hydrolysis resistance</s0>
<s5>08</s5>
</fC03>
<fC03 i1="07" i2="X" l="SPA">
<s0>Resistencia hidrólisis</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="FRE">
<s0>Activité biologique</s0>
<s5>09</s5>
</fC03>
<fC03 i1="08" i2="X" l="ENG">
<s0>Biological activity</s0>
<s5>09</s5>
</fC03>
<fC03 i1="08" i2="X" l="SPA">
<s0>Actividad biológica</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="FRE">
<s0>Synthèse chimique</s0>
<s5>10</s5>
</fC03>
<fC03 i1="09" i2="X" l="ENG">
<s0>Chemical synthesis</s0>
<s5>10</s5>
</fC03>
<fC03 i1="09" i2="X" l="SPA">
<s0>Síntesis química</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="FRE">
<s0>Synthèse peptidique</s0>
<s5>11</s5>
</fC03>
<fC03 i1="10" i2="X" l="ENG">
<s0>Peptide synthesis</s0>
<s5>11</s5>
</fC03>
<fC03 i1="10" i2="X" l="SPA">
<s0>Síntesis peptídica</s0>
<s5>11</s5>
</fC03>
<fC03 i1="11" i2="X" l="FRE">
<s0>In vitro</s0>
<s5>12</s5>
</fC03>
<fC03 i1="11" i2="X" l="ENG">
<s0>In vitro</s0>
<s5>12</s5>
</fC03>
<fC03 i1="11" i2="X" l="SPA">
<s0>In vitro</s0>
<s5>12</s5>
</fC03>
<fC03 i1="12" i2="X" l="FRE">
<s0>Inhibiteur enzyme</s0>
<s5>32</s5>
</fC03>
<fC03 i1="12" i2="X" l="ENG">
<s0>Enzyme inhibitor</s0>
<s5>32</s5>
</fC03>
<fC03 i1="12" i2="X" l="SPA">
<s0>Inhibidor enzima</s0>
<s5>32</s5>
</fC03>
<fC03 i1="13" i2="X" l="FRE">
<s0>Glutamique acide(acétylthréonyl-séryl-alanyl-valyl-leucyl-1-désoxy)</s0>
<s4>INC</s4>
<s5>76</s5>
</fC03>
<fC07 i1="01" i2="X" l="FRE">
<s0>Peptidases</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="01" i2="X" l="ENG">
<s0>Peptidases</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="01" i2="X" l="SPA">
<s0>Peptidases</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="02" i2="X" l="FRE">
<s0>Hydrolases</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="02" i2="X" l="ENG">
<s0>Hydrolases</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="02" i2="X" l="SPA">
<s0>Hydrolases</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="03" i2="X" l="FRE">
<s0>Enzyme</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="03" i2="X" l="ENG">
<s0>Enzyme</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="03" i2="X" l="SPA">
<s0>Enzima</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="04" i2="X" l="FRE">
<s0>Coronavirus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="04" i2="X" l="ENG">
<s0>Coronavirus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="04" i2="X" l="SPA">
<s0>Coronavirus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="05" i2="X" l="FRE">
<s0>Coronaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="05" i2="X" l="ENG">
<s0>Coronaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="05" i2="X" l="SPA">
<s0>Coronaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="06" i2="X" l="FRE">
<s0>Nidovirales</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="06" i2="X" l="ENG">
<s0>Nidovirales</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="06" i2="X" l="SPA">
<s0>Nidovirales</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="07" i2="X" l="FRE">
<s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="07" i2="X" l="ENG">
<s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="07" i2="X" l="SPA">
<s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fN21>
<s1>026</s1>
</fN21>
</pA>
</standard>
</inist>
</record>

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   |wiki=    Sante
   |area=    SrasV1
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   |texte=   Evaluation of peptide-aldehyde inhibitors using R188I mutant of SARS 3CL protease as a proteolysis-resistant mutant
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