‘Click peptide’: a novel ‘O‐acyl isopeptide method’ for peptide synthesis and chemical biology‐oriented synthesis of amyloid β peptide analogues
Identifieur interne : 000F06 ( Istex/Corpus ); précédent : 000F05; suivant : 000F07‘Click peptide’: a novel ‘O‐acyl isopeptide method’ for peptide synthesis and chemical biology‐oriented synthesis of amyloid β peptide analogues
Auteurs : Youhei Sohma ; Atsuhiko Taniguchi ; Taku Yoshiya ; Yousuke Chiyomori ; Fukue Fukao ; Setsuko Nakamura ; Mariusz Skwarczynski ; Takuma Okada ; Keisuke Ikeda ; Yoshio Hayashi ; Tooru Kimura ; Shun Hirota ; Katsumi Matsuzaki ; Yoshiaki KisoSource :
- Journal of Peptide Science [ 1075-2617 ] ; 2006-12.
English descriptors
- Teeft :
- Acyl, Amyloid, Amyloid peptide, Aspartic protease inhibitors, Chem, Chemical synthesis, Click, Click peptide, Copyright, European peptide society, Hayashi, Inhibitor, Intramolecular, Intramolecular acyl migration, Intramolecular acyl migration reaction, Isodipeptide unit, Isopeptide, Isopeptide method, Isopeptide structure, John wiley sons, Kimura, Kiso, Lett, Native amide bond, Native peptides, Pept, Peptide, Peptide chemistry, Peptide derivatives, Peptide synthesis, Physiological conditions, Prodrugs, Protease, Protease inhibitors, Protective group, Sohma, Tetrahedron lett.
Abstract
After over a decade of studies on aspartic protease inhibitors and water‐soluble prodrugs, we have been developing a novel method, since 2003, called ‘O‐acyl isopeptide method’, for the synthesis of peptides containing difficult sequences. With our recent discoveries of ‘O‐acyl isodipeptide unit’ and the ‘racemization‐free segment condensation method’, this method has further evolved as a general synthetic method for peptides. Moreover, ‘Click Peptide’, which could be a powerful tool for identifying the pathological functions of amyloid β peptides in Alzheimer's disease, represents a valuable use of the isopeptide method in Chemical Biology‐oriented research. Copyright © 2006 European Peptide Society and John Wiley & Sons, Ltd.
Url:
DOI: 10.1002/psc.817
Links to Exploration step
ISTEX:D25C14EDAA4CD049907633A397EAFC5EDD73C1CELe document en format XML
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Taniguchi</name><affiliation><mods:affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</mods:affiliation></affiliation></author><author><name sortKey="Yoshiya, Taku" sort="Yoshiya, Taku" uniqKey="Yoshiya T" first="Taku" last="Yoshiya">Taku Yoshiya</name><affiliation><mods:affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</mods:affiliation></affiliation></author><author><name sortKey="Chiyomori, Yousuke" sort="Chiyomori, Yousuke" uniqKey="Chiyomori Y" first="Yousuke" last="Chiyomori">Yousuke Chiyomori</name><affiliation><mods:affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 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332‐0012</mods:affiliation></affiliation></author><author><name sortKey="Matsuzaki, Katsumi" sort="Matsuzaki, Katsumi" uniqKey="Matsuzaki K" first="Katsumi" last="Matsuzaki">Katsumi Matsuzaki</name><affiliation><mods:affiliation>Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo‐ku, Kyoto 606‐8501, Japan</mods:affiliation></affiliation></author><author><name sortKey="Kiso, Yoshiaki" sort="Kiso, Yoshiaki" uniqKey="Kiso Y" first="Yoshiaki" last="Kiso">Yoshiaki Kiso</name><affiliation><mods:affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</mods:affiliation></affiliation><affiliation><mods:affiliation>E-mail: kiso@mb.kyoto‐phu.ac.jp</mods:affiliation></affiliation><affiliation><mods:affiliation>Correspondence address: Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412, Japan</mods:affiliation></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:D25C14EDAA4CD049907633A397EAFC5EDD73C1CE</idno><date when="2006" year="2006">2006</date><idno type="doi">10.1002/psc.817</idno><idno type="url">https://api.istex.fr/ark:/67375/WNG-J20K3PKX-B/fulltext.pdf</idno><idno type="wicri:Area/Istex/Corpus">000F06</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Corpus" wicri:corpus="ISTEX">000F06</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a" type="main">‘Click peptide’: a novel ‘O‐acyl isopeptide method’ for peptide synthesis and chemical biology‐oriented synthesis of amyloid β peptide analogues</title><author><name sortKey="Sohma, Youhei" sort="Sohma, Youhei" uniqKey="Sohma Y" first="Youhei" last="Sohma">Youhei Sohma</name><affiliation><mods:affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</mods:affiliation></affiliation><affiliation><mods:affiliation>Department of Physical Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</mods:affiliation></affiliation></author><author><name sortKey="Taniguchi, Atsuhiko" sort="Taniguchi, Atsuhiko" uniqKey="Taniguchi A" first="Atsuhiko" last="Taniguchi">Atsuhiko Taniguchi</name><affiliation><mods:affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</mods:affiliation></affiliation></author><author><name sortKey="Yoshiya, Taku" sort="Yoshiya, Taku" uniqKey="Yoshiya T" first="Taku" last="Yoshiya">Taku Yoshiya</name><affiliation><mods:affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</mods:affiliation></affiliation></author><author><name sortKey="Chiyomori, Yousuke" sort="Chiyomori, Yousuke" uniqKey="Chiyomori Y" first="Yousuke" last="Chiyomori">Yousuke Chiyomori</name><affiliation><mods:affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</mods:affiliation></affiliation></author><author><name sortKey="Fukao, Fukue" sort="Fukao, Fukue" uniqKey="Fukao F" first="Fukue" last="Fukao">Fukue Fukao</name><affiliation><mods:affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</mods:affiliation></affiliation></author><author><name sortKey="Nakamura, Setsuko" sort="Nakamura, Setsuko" uniqKey="Nakamura S" first="Setsuko" last="Nakamura">Setsuko Nakamura</name><affiliation><mods:affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</mods:affiliation></affiliation></author><author><name sortKey="Skwarczynski, Mariusz" sort="Skwarczynski, Mariusz" uniqKey="Skwarczynski M" first="Mariusz" last="Skwarczynski">Mariusz Skwarczynski</name><affiliation><mods:affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</mods:affiliation></affiliation></author><author><name sortKey="Okada, Takuma" sort="Okada, Takuma" uniqKey="Okada T" first="Takuma" last="Okada">Takuma Okada</name><affiliation><mods:affiliation>Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo‐ku, Kyoto 606‐8501, Japan</mods:affiliation></affiliation></author><author><name sortKey="Ikeda, Keisuke" sort="Ikeda, Keisuke" uniqKey="Ikeda K" first="Keisuke" last="Ikeda">Keisuke Ikeda</name><affiliation><mods:affiliation>Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo‐ku, Kyoto 606‐8501, Japan</mods:affiliation></affiliation></author><author><name sortKey="Hayashi, Yoshio" sort="Hayashi, Yoshio" uniqKey="Hayashi Y" first="Yoshio" last="Hayashi">Yoshio Hayashi</name><affiliation><mods:affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</mods:affiliation></affiliation></author><author><name sortKey="Kimura, Tooru" sort="Kimura, Tooru" uniqKey="Kimura T" first="Tooru" last="Kimura">Tooru Kimura</name><affiliation><mods:affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</mods:affiliation></affiliation></author><author><name sortKey="Hirota, Shun" sort="Hirota, Shun" uniqKey="Hirota S" first="Shun" last="Hirota">Shun Hirota</name><affiliation><mods:affiliation>Department of Physical Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</mods:affiliation></affiliation><affiliation><mods:affiliation>PRESTO, JST, Kawaguchi, Saitama 332‐0012</mods:affiliation></affiliation></author><author><name sortKey="Matsuzaki, Katsumi" sort="Matsuzaki, Katsumi" uniqKey="Matsuzaki K" first="Katsumi" last="Matsuzaki">Katsumi Matsuzaki</name><affiliation><mods:affiliation>Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo‐ku, Kyoto 606‐8501, Japan</mods:affiliation></affiliation></author><author><name sortKey="Kiso, Yoshiaki" sort="Kiso, Yoshiaki" uniqKey="Kiso Y" first="Yoshiaki" last="Kiso">Yoshiaki Kiso</name><affiliation><mods:affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</mods:affiliation></affiliation><affiliation><mods:affiliation>E-mail: kiso@mb.kyoto‐phu.ac.jp</mods:affiliation></affiliation><affiliation><mods:affiliation>Correspondence address: Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412, Japan</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Journal of Peptide Science</title><title level="j" type="sub">10th Naples Workshop on Bioactive Peptides</title><title level="j" type="alt">JOURNAL OF PEPTIDE SCIENCE</title><idno type="ISSN">1075-2617</idno><idno type="eISSN">1099-1387</idno><imprint><biblScope unit="vol">12</biblScope><biblScope unit="issue">12</biblScope><biblScope unit="page" from="823">823</biblScope><biblScope unit="page" to="828">828</biblScope><biblScope unit="page-count">6</biblScope><publisher>John Wiley & Sons, Ltd.</publisher><pubPlace>Chichester, UK</pubPlace><date type="published" when="2006-12">2006-12</date></imprint><idno type="ISSN">1075-2617</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1075-2617</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="Teeft" xml:lang="en"><term>Acyl</term><term>Amyloid</term><term>Amyloid peptide</term><term>Aspartic protease inhibitors</term><term>Chem</term><term>Chemical synthesis</term><term>Click</term><term>Click peptide</term><term>Copyright</term><term>European peptide society</term><term>Hayashi</term><term>Inhibitor</term><term>Intramolecular</term><term>Intramolecular acyl migration</term><term>Intramolecular acyl migration reaction</term><term>Isodipeptide unit</term><term>Isopeptide</term><term>Isopeptide method</term><term>Isopeptide structure</term><term>John wiley sons</term><term>Kimura</term><term>Kiso</term><term>Lett</term><term>Native amide bond</term><term>Native peptides</term><term>Pept</term><term>Peptide</term><term>Peptide chemistry</term><term>Peptide derivatives</term><term>Peptide synthesis</term><term>Physiological conditions</term><term>Prodrugs</term><term>Protease</term><term>Protease inhibitors</term><term>Protective group</term><term>Sohma</term><term>Tetrahedron lett</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">After over a decade of studies on aspartic protease inhibitors and water‐soluble prodrugs, we have been developing a novel method, since 2003, called ‘O‐acyl isopeptide method’, for the synthesis of peptides containing difficult sequences. With our recent discoveries of ‘O‐acyl isodipeptide unit’ and the ‘racemization‐free segment condensation method’, this method has further evolved as a general synthetic method for peptides. Moreover, ‘Click Peptide’, which could be a powerful tool for identifying the pathological functions of amyloid β peptides in Alzheimer's disease, represents a valuable use of the isopeptide method in Chemical Biology‐oriented research. Copyright © 2006 European Peptide Society and John Wiley & Sons, Ltd.</div></front></TEI><istex><corpusName>wiley</corpusName><keywords><teeft><json:string>peptide</json:string><json:string>isopeptide</json:string><json:string>isopeptide method</json:string><json:string>acyl</json:string><json:string>kiso</json:string><json:string>click peptide</json:string><json:string>kimura</json:string><json:string>amyloid</json:string><json:string>intramolecular</json:string><json:string>sohma</json:string><json:string>chem</json:string><json:string>hayashi</json:string><json:string>pept</json:string><json:string>intramolecular acyl migration reaction</json:string><json:string>prodrugs</json:string><json:string>john wiley sons</json:string><json:string>lett</json:string><json:string>copyright</json:string><json:string>european peptide society</json:string><json:string>peptide synthesis</json:string><json:string>protease</json:string><json:string>peptide chemistry</json:string><json:string>isodipeptide unit</json:string><json:string>amyloid peptide</json:string><json:string>click</json:string><json:string>chemical synthesis</json:string><json:string>intramolecular acyl migration</json:string><json:string>isopeptide structure</json:string><json:string>aspartic protease inhibitors</json:string><json:string>tetrahedron lett</json:string><json:string>protective group</json:string><json:string>protease inhibitors</json:string><json:string>physiological conditions</json:string><json:string>native peptides</json:string><json:string>peptide derivatives</json:string><json:string>native amide bond</json:string><json:string>inhibitor</json:string></teeft></keywords><author><json:item><name>Youhei Sohma</name><affiliations><json:string>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</json:string><json:string>Department of Physical Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</json:string></affiliations></json:item><json:item><name>Atsuhiko Taniguchi</name><affiliations><json:string>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</json:string></affiliations></json:item><json:item><name>Taku Yoshiya</name><affiliations><json:string>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</json:string></affiliations></json:item><json:item><name>Yousuke Chiyomori</name><affiliations><json:string>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</json:string></affiliations></json:item><json:item><name>Fukue Fukao</name><affiliations><json:string>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</json:string></affiliations></json:item><json:item><name>Setsuko Nakamura</name><affiliations><json:string>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</json:string></affiliations></json:item><json:item><name>Mariusz Skwarczynski</name><affiliations><json:string>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</json:string></affiliations></json:item><json:item><name>Takuma Okada</name><affiliations><json:string>Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo‐ku, Kyoto 606‐8501, Japan</json:string></affiliations></json:item><json:item><name>Keisuke Ikeda</name><affiliations><json:string>Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo‐ku, Kyoto 606‐8501, Japan</json:string></affiliations></json:item><json:item><name>Yoshio Hayashi</name><affiliations><json:string>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</json:string></affiliations></json:item><json:item><name>Tooru Kimura</name><affiliations><json:string>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</json:string></affiliations></json:item><json:item><name>Shun Hirota</name><affiliations><json:string>Department of Physical Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</json:string><json:string>PRESTO, JST, Kawaguchi, Saitama 332‐0012</json:string></affiliations></json:item><json:item><name>Katsumi Matsuzaki</name><affiliations><json:string>Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo‐ku, Kyoto 606‐8501, Japan</json:string></affiliations></json:item><json:item><name>Yoshiaki Kiso</name><affiliations><json:string>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</json:string><json:string>E-mail: kiso@mb.kyoto‐phu.ac.jp</json:string><json:string>Correspondence address: Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412, Japan</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>O‐acyl isopeptide method</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Alzheimer's disease</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>amyloid β peptide</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>click peptide</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>difficult sequence</value></json:item></subject><articleId><json:string>PSC817</json:string></articleId><arkIstex>ark:/67375/WNG-J20K3PKX-B</arkIstex><language><json:string>eng</json:string></language><originalGenre><json:string>article</json:string></originalGenre><abstract>After over a decade of studies on aspartic protease inhibitors and water‐soluble prodrugs, we have been developing a novel method, since 2003, called ‘O‐acyl isopeptide method’, for the synthesis of peptides containing difficult sequences. With our recent discoveries of ‘O‐acyl isodipeptide unit’ and the ‘racemization‐free segment condensation method’, this method has further evolved as a general synthetic method for peptides. Moreover, ‘Click Peptide’, which could be a powerful tool for identifying the pathological functions of amyloid β peptides in Alzheimer's disease, represents a valuable use of the isopeptide method in Chemical Biology‐oriented research. Copyright © 2006 European Peptide Society and John Wiley & Sons, Ltd.</abstract><qualityIndicators><score>5.651</score><pdfWordCount>2391</pdfWordCount><pdfCharCount>16954</pdfCharCount><pdfVersion>1.3</pdfVersion><pdfPageCount>6</pdfPageCount><pdfPageSize>595 x 791 pts</pdfPageSize><pdfWordsPerPage>399</pdfWordsPerPage><pdfText>true</pdfText><refBibsNative>true</refBibsNative><abstractWordCount>105</abstractWordCount><abstractCharCount>737</abstractCharCount><keywordCount>5</keywordCount></qualityIndicators><title>‘Click peptide’: a novel ‘O‐acyl isopeptide method’ for peptide synthesis and chemical biology‐oriented synthesis of amyloid β peptide analogues</title><pmid><json:string>17131295</json:string></pmid><genre><json:string>article</json:string></genre><host><title>Journal of Peptide Science</title><language><json:string>unknown</json:string></language><doi><json:string>10.1002/(ISSN)1099-1387</json:string></doi><issn><json:string>1075-2617</json:string></issn><eissn><json:string>1099-1387</json:string></eissn><publisherId><json:string>PSC</json:string></publisherId><volume>12</volume><issue>12</issue><pages><first>823</first><last>828</last><total>6</total></pages><genre><json:string>journal</json:string></genre><author><json:item><name>Ettore Benedetti</name></json:item></author><subject><json:item><value>Research Article</value></json:item><json:item><value>Research Articles</value></json:item></subject></host><namedEntities><unitex><date><json:string>the 21st Century</json:string><json:string>21st Century</json:string><json:string>2006</json:string><json:string>2003</json:string></date><geogName></geogName><orgName><json:string>Japan Received</json:string><json:string>Research Fellowships of JSPS for Young Scientists</json:string><json:string>Ministry of Education, Culture, Sports, Science and Technology</json:string><json:string>H O CO</json:string><json:string>H CO</json:string><json:string>Sons, Ltd.</json:string><json:string>Kyoto University</json:string><json:string>Department of Medicinal Chemistry, Center for Frontier Research</json:string><json:string>Sons, Ltd</json:string><json:string>Kyoto Pharmaceutical University</json:string><json:string>Department of Physical Chemistry</json:string></orgName><orgName_funder></orgName_funder><orgName_provider></orgName_provider><persName><json:string>Ala Glu</json:string><json:string>John Wiley</json:string><json:string>Peptide Society</json:string><json:string>Met Leu</json:string><json:string>Val Phe</json:string><json:string>Ala Asn</json:string><json:string>T. 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With our recent discoveries of ‘<i>O</i>‐acyl isodipeptide unit’ and the ‘racemization‐free segment condensation method’, this method has further evolved as a general synthetic method for peptides. Moreover, ‘Click Peptide’, which could be a powerful tool for identifying the pathological functions of amyloid β peptides in Alzheimer's disease, represents a valuable use of the isopeptide method in Chemical Biology‐oriented research. Copyright © 2006 European Peptide Society and John Wiley & Sons, Ltd.</p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>‘Click peptide’: a novel ‘O‐acyl isopeptide method’ for peptide synthesis and chemical biology‐oriented synthesis of amyloid β peptide analogues</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>O‐ACYL ISOPEPTIDE METHOD IN PEPTIDE CHEMISTRY</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>‘Click peptide’: a novel ‘O‐acyl isopeptide method’ for peptide synthesis and chemical biology‐oriented synthesis of amyloid β peptide analogues</title></titleInfo><name type="personal"><namePart type="given">Youhei</namePart><namePart type="family">Sohma</namePart><affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</affiliation><affiliation>Department of Physical Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Atsuhiko</namePart><namePart type="family">Taniguchi</namePart><affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Taku</namePart><namePart type="family">Yoshiya</namePart><affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Yousuke</namePart><namePart type="family">Chiyomori</namePart><affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Fukue</namePart><namePart type="family">Fukao</namePart><affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Setsuko</namePart><namePart type="family">Nakamura</namePart><affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Mariusz</namePart><namePart type="family">Skwarczynski</namePart><affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Takuma</namePart><namePart type="family">Okada</namePart><affiliation>Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo‐ku, Kyoto 606‐8501, Japan</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Keisuke</namePart><namePart type="family">Ikeda</namePart><affiliation>Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo‐ku, Kyoto 606‐8501, Japan</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Yoshio</namePart><namePart type="family">Hayashi</namePart><affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Tooru</namePart><namePart type="family">Kimura</namePart><affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Shun</namePart><namePart type="family">Hirota</namePart><affiliation>Department of Physical Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</affiliation><affiliation>PRESTO, JST, Kawaguchi, Saitama 332‐0012</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Katsumi</namePart><namePart type="family">Matsuzaki</namePart><affiliation>Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo‐ku, Kyoto 606‐8501, Japan</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Yoshiaki</namePart><namePart type="family">Kiso</namePart><affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412</affiliation><affiliation>E-mail: kiso@mb.kyoto‐phu.ac.jp</affiliation><affiliation>Correspondence address: Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina‐ku, Kyoto 607‐8412, Japan</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D">article</genre><originInfo><publisher>John Wiley & Sons, Ltd.</publisher><place><placeTerm type="text">Chichester, UK</placeTerm></place><dateIssued encoding="w3cdtf">2006-12</dateIssued><dateCaptured encoding="w3cdtf">2006-07-28</dateCaptured><dateValid encoding="w3cdtf">2006-09-20</dateValid><copyrightDate encoding="w3cdtf">2006</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><extent unit="figures">5</extent><extent unit="tables">0</extent><extent unit="references">32</extent></physicalDescription><abstract lang="en">After over a decade of studies on aspartic protease inhibitors and water‐soluble prodrugs, we have been developing a novel method, since 2003, called ‘O‐acyl isopeptide method’, for the synthesis of peptides containing difficult sequences. With our recent discoveries of ‘O‐acyl isodipeptide unit’ and the ‘racemization‐free segment condensation method’, this method has further evolved as a general synthetic method for peptides. Moreover, ‘Click Peptide’, which could be a powerful tool for identifying the pathological functions of amyloid β peptides in Alzheimer's disease, represents a valuable use of the isopeptide method in Chemical Biology‐oriented research. Copyright © 2006 European Peptide Society and John Wiley & Sons, Ltd.</abstract><note type="funding">MEXT (Ministry of Education, Culture, Sports, Science and Technology)</note><subject lang="en"><genre>keywords</genre><topic>O‐acyl isopeptide method</topic><topic>Alzheimer's disease</topic><topic>amyloid β peptide</topic><topic>click peptide</topic><topic>difficult sequence</topic></subject><relatedItem type="host"><titleInfo><title>Journal of Peptide Science</title><subTitle>An Official Publication of the European Peptide Society</subTitle></titleInfo><titleInfo type="abbreviated"><title>J. Peptide Sci.</title></titleInfo><name type="personal"><namePart type="given">Ettore</namePart><namePart type="family">Benedetti</namePart></name><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><subject><genre>article-category</genre><topic>Research Article</topic><topic>Research Articles</topic></subject><identifier type="ISSN">1075-2617</identifier><identifier type="eISSN">1099-1387</identifier><identifier type="DOI">10.1002/(ISSN)1099-1387</identifier><identifier type="PublisherID">PSC</identifier><part><date>2006</date><detail type="title"><title>10th Naples Workshop on Bioactive Peptides</title></detail><detail type="volume"><caption>vol.</caption><number>12</number></detail><detail type="issue"><caption>no.</caption><number>12</number></detail><extent unit="pages"><start>823</start><end>828</end><total>6</total></extent></part></relatedItem><relatedItem type="references" displayLabel="cit1"><titleInfo><title>A novel approach for the hydrophobic peptides synthesis and purification through ON intramolecular acyl migration reaction</title></titleInfo><name type="personal"><namePart type="given">Y</namePart><namePart type="family">Sohma</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M</namePart><namePart type="family">Sasaki</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Z</namePart><namePart type="family">Ziora</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">N</namePart><namePart type="family">Takahashi</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">T</namePart><namePart type="family">Kimura</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Y</namePart><namePart type="family">Hayashi</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Y</namePart><namePart type="family">Kiso</namePart><role><roleTerm type="text">author</roleTerm></role></name><genre>book-chapter</genre><relatedItem type="host"><titleInfo><title>Peptides, Peptide Revolution: Genomics, Proteomics and Therapeutics</title></titleInfo><originInfo><publisher>Kluwer Academic</publisher><place><placeTerm type="text">Netherlands</placeTerm></place></originInfo><part><date>2003</date><extent unit="pages"><start>67</start><end>68</end></extent></part></relatedItem></relatedItem><relatedItem type="references" displayLabel="cit2"><titleInfo><title>Novel and efficient synthesis of difficult sequence‐containing peptides through ON intramolecular acyl migration reaction of O‐acyl isopeptides</title></titleInfo><name type="personal"><namePart type="given">Y</namePart><namePart type="family">Sohma</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M</namePart><namePart type="family">Sasaki</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Y</namePart><namePart type="family">Hayashi</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">T</namePart><namePart type="family">Kimura</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Y</namePart><namePart type="family">Kiso</namePart><role><roleTerm type="text">author</roleTerm></role></name><genre>journal-article</genre><note type="citation/reference">Sohma Y, Sasaki M, Hayashi Y, Kimura T, Kiso Y. Novel and efficient synthesis of difficult sequence‐containing peptides through ON intramolecular acyl migration reaction of O‐acyl isopeptides. Chem. Commun. 2004; 124–125, (First published as an Advanced Article on the web 21st November 2003).</note><part><date>2004</date><extent unit="pages"><start>124</start><end>125</end></extent></part><relatedItem type="host"><titleInfo><title>Chem. Commun.</title></titleInfo><part><date>2004</date><extent unit="pages"><start>124</start><end>125</end></extent></part></relatedItem></relatedItem><relatedItem type="references" displayLabel="cit3"><titleInfo><title>Design and synthesis of a novel water‐soluble Aβ1‐42 isopeptide: an efficient strategy for the preparation of Alzheimer's disease‐related peptide, Aβ1‐42, via ON intramolecular acyl migration reaction</title></titleInfo><name type="personal"><namePart type="given">Y</namePart><namePart type="family">Sohma</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M</namePart><namePart type="family">Sasaki</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Y</namePart><namePart type="family">Hayashi</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">T</namePart><namePart type="family">Kimura</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Y</namePart><namePart type="family">Kiso</namePart><role><roleTerm type="text">author</roleTerm></role></name><genre>journal-article</genre><note type="citation/reference">Sohma Y, Sasaki M, Hayashi Y, Kimura T, Kiso Y. Design and synthesis of a novel water‐soluble Aβ1‐42 isopeptide: an efficient strategy for the preparation of Alzheimer's disease‐related peptide, Aβ1‐42, via ON intramolecular acyl migration reaction. Tetrahedron Lett. 2004; 45: 5965–5968.</note><part><date>2004</date><detail type="volume"><caption>vol.</caption><number>45</number></detail><extent unit="pages"><start>5965</start><end>5968</end></extent></part><relatedItem type="host"><titleInfo><title>Tetrahedron Lett.</title></titleInfo><part><date>2004</date><detail type="volume"><caption>vol.</caption><number>45</number></detail><extent unit="pages"><start>5965</start><end>5968</end></extent></part></relatedItem></relatedItem><relatedItem type="references" displayLabel="cit4"><titleInfo><title>ON intramolecular acyl migration reaction in the development of prodrugs and the synthesis of difficult sequence‐containing bioactive peptides</title></titleInfo><name type="personal"><namePart type="given">Y</namePart><namePart type="family">Sohma</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Y</namePart><namePart type="family">Hayashi</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M</namePart><namePart type="family">Skwarczynski</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Y</namePart><namePart type="family">Hamada</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M</namePart><namePart type="family">Sasaki</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">T</namePart><namePart type="family">Kimura</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Y</namePart><namePart type="family">Kiso</namePart><role><roleTerm type="text">author</roleTerm></role></name><genre>journal-article</genre><note type="citation/reference">Sohma Y, Hayashi Y, Skwarczynski M, Hamada Y, Sasaki M, Kimura T, Kiso Y. ON intramolecular acyl migration reaction in the development of prodrugs and the synthesis of difficult sequence‐containing bioactive peptides. Biopolymers 2004; 76: 344–356.</note><part><date>2004</date><detail type="volume"><caption>vol.</caption><number>76</number></detail><extent unit="pages"><start>344</start><end>356</end></extent></part><relatedItem type="host"><titleInfo><title>Biopolymers</title></titleInfo><part><date>2004</date><detail type="volume"><caption>vol.</caption><number>76</number></detail><extent unit="pages"><start>344</start><end>356</end></extent></part></relatedItem></relatedItem><relatedItem type="references" displayLabel="cit5"><titleInfo><title>“O‐Acyl isopeptide method” for the synthesis of difficult sequence‐containing peptides: application in the synthesis of Alzheimer's disease‐related amyloid β peptide (Aβ) 1–42</title></titleInfo><name type="personal"><namePart type="given">Y</namePart><namePart type="family">Sohma</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Y</namePart><namePart type="family">Hayashi</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M</namePart><namePart type="family">Kimura</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Y</namePart><namePart type="family">Chiyomori</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">A</namePart><namePart type="family">Taniguchi</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M</namePart><namePart type="family">Sasaki</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">T</namePart><namePart type="family">Kimura</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Y</namePart><namePart type="family">Kiso</namePart><role><roleTerm type="text">author</roleTerm></role></name><genre>journal-article</genre><note type="citation/reference">Sohma Y, Hayashi Y, Kimura M, Chiyomori Y, Taniguchi A, Sasaki M, Kimura T, Kiso Y. “O‐Acyl isopeptide method” for the synthesis of difficult sequence‐containing peptides: application in the synthesis of Alzheimer's disease‐related amyloid β peptide (Aβ) 1–42. 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