Synthesis and structure of AzAsx-Pro-containing Aza-peptides
Identifieur interne : 000670 ( Istex/Corpus ); précédent : 000669; suivant : 000671Synthesis and structure of AzAsx-Pro-containing Aza-peptides
Auteurs : Frédéric André ; Michel Marraud ; Guy Boussard ; Claude Didierjean ; André AubrySource :
- Tetrahedron Letters [ 0040-4039 ] ; 1995.
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Abstract
Abstract: One possible α-modification in peptides is the substitution of a nitrogen for the CαH group. We propose triphosgene as a carbonylating agent for coupling the properly substituted hydrazide to the proline nitrogen to obtain the AzAsx-Pro or AzAla-Pro aza-sequence (Az denotes the N CαH replacement, and Asx stands for Asn or Asp). The structure of three Z-AzAsx-Pro-NHiPr and of the Boc-AzAla-Pro-NHiPr aza dipeptides has been studied in solution by 1H-NMR and IR spectroscopy, and three of them have been investigated in the crystalline state by X-ray diffraction.
Url:
DOI: 10.1016/0040-4039(95)02124-8
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ISTEX:6F33326EE98EC3ED18CDB5FED0348D4A132A00FBLe document en format XML
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associé au CNRS, ENSIC-INPL, BP 451, 54001 Nancy, France</mods:affiliation></affiliation></author><author><name sortKey="Boussard, Guy" sort="Boussard, Guy" uniqKey="Boussard G" first="Guy" last="Boussard">Guy Boussard</name><affiliation><mods:affiliation>Laboratoire de Chimie Physique Macromoléculaire, associé au CNRS, ENSIC-INPL, BP 451, 54001 Nancy, France</mods:affiliation></affiliation></author><author><name sortKey="Didierjean, Claude" sort="Didierjean, Claude" uniqKey="Didierjean C" first="Claude" last="Didierjean">Claude Didierjean</name><affiliation><mods:affiliation>Laboratoire de Cristallographie et Modélisation des Matériaux Minéraux et Biologiques, associé au CNRS, Université de Nancy I, BP 239, 54506 Vandoeuvre, France</mods:affiliation></affiliation></author><author><name sortKey="Aubry, Andre" sort="Aubry, Andre" uniqKey="Aubry A" first="André" last="Aubry">André Aubry</name><affiliation><mods:affiliation>Laboratoire de Cristallographie et Modélisation des Matériaux Minéraux et Biologiques, associé au CNRS, Université de Nancy I, BP 239, 54506 Vandoeuvre, France</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j">Tetrahedron Letters</title><title level="j" type="abbrev">TETL</title><idno type="ISSN">0040-4039</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1995">1995</date><biblScope unit="volume">37</biblScope><biblScope unit="issue">2</biblScope><biblScope unit="page" from="183">183</biblScope><biblScope unit="page" to="186">186</biblScope></imprint><idno type="ISSN">0040-4039</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0040-4039</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amide</term><term>Amide bond</term><term>Amino</term><term>Amino acids</term><term>Azxaa</term><term>Carbonylating agent</term><term>Crystal structures</term><term>Intramolecular hydrogen bond</term><term>Marcel dekker</term><term>Peptide</term><term>Peptide analogues</term><term>Proline</term><term>Proline nitrogen</term><term>Side chain</term><term>Standard distance</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>Amide</term><term>Amide bond</term><term>Amino</term><term>Amino acids</term><term>Azxaa</term><term>Carbonylating agent</term><term>Crystal structures</term><term>Intramolecular hydrogen bond</term><term>Marcel dekker</term><term>Peptide</term><term>Peptide analogues</term><term>Proline</term><term>Proline nitrogen</term><term>Side chain</term><term>Standard distance</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Abstract: One possible α-modification in peptides is the substitution of a nitrogen for the CαH group. We propose triphosgene as a carbonylating agent for coupling the properly substituted hydrazide to the proline nitrogen to obtain the AzAsx-Pro or AzAla-Pro aza-sequence (Az denotes the N CαH replacement, and Asx stands for Asn or Asp). The structure of three Z-AzAsx-Pro-NHiPr and of the Boc-AzAla-Pro-NHiPr aza dipeptides has been studied in solution by 1H-NMR and IR spectroscopy, and three of them have been investigated in the crystalline state by X-ray diffraction.</div></front></TEI><istex><corpusName>elsevier</corpusName><keywords><teeft><json:string>peptide</json:string><json:string>proline</json:string><json:string>azxaa</json:string><json:string>amide</json:string><json:string>peptide analogues</json:string><json:string>marcel dekker</json:string><json:string>side chain</json:string><json:string>carbonylating agent</json:string><json:string>crystal structures</json:string><json:string>standard distance</json:string><json:string>intramolecular hydrogen bond</json:string><json:string>amide bond</json:string><json:string>proline nitrogen</json:string><json:string>amino acids</json:string><json:string>amino</json:string></teeft></keywords><author><json:item><name>Frédéric André</name><affiliations><json:string>Laboratoire de Chimie Physique Macromoléculaire, associé au CNRS, ENSIC-INPL, BP 451, 54001 Nancy, France</json:string></affiliations></json:item><json:item><name>Michel Marraud</name><affiliations><json:string>Laboratoire de Chimie Physique Macromoléculaire, associé au CNRS, ENSIC-INPL, BP 451, 54001 Nancy, France</json:string></affiliations></json:item><json:item><name>Guy Boussard</name><affiliations><json:string>Laboratoire de Chimie Physique Macromoléculaire, associé au CNRS, ENSIC-INPL, BP 451, 54001 Nancy, France</json:string></affiliations></json:item><json:item><name>Claude Didierjean</name><affiliations><json:string>Laboratoire de Cristallographie et Modélisation des Matériaux Minéraux et Biologiques, associé au CNRS, Université de Nancy I, BP 239, 54506 Vandoeuvre, France</json:string></affiliations></json:item><json:item><name>André Aubry</name><affiliations><json:string>Laboratoire de Cristallographie et Modélisation des Matériaux Minéraux et Biologiques, associé au CNRS, Université de Nancy I, BP 239, 54506 Vandoeuvre, France</json:string></affiliations></json:item></author><language><json:string>eng</json:string></language><originalGenre><json:string>Full-length article</json:string></originalGenre><abstract>One possible α-modification in peptides is the substitution of a nitrogen for the CαH group. We propose triphosgene as a carbonylating agent for coupling the properly substituted hydrazide to the proline nitrogen to obtain the AzAsx-Pro or AzAla-Pro aza-sequence (Az denotes the N CαH replacement, and Asx stands for Asn or Asp). The structure of three Z-AzAsx-Pro-NHiPr and of the Boc-AzAla-Pro-NHiPr aza dipeptides has been studied in solution by 1H-NMR and IR spectroscopy, and three of them have been investigated in the crystalline state by X-ray diffraction.</abstract><qualityIndicators><score>2.51</score><pdfVersion>1.2</pdfVersion><pdfPageSize>533 x 749 pts</pdfPageSize><refBibsNative>true</refBibsNative><keywordCount>0</keywordCount><abstractCharCount>564</abstractCharCount><pdfWordCount>1466</pdfWordCount><pdfCharCount>9146</pdfCharCount><pdfPageCount>4</pdfPageCount><abstractWordCount>87</abstractWordCount></qualityIndicators><title>Synthesis and structure of AzAsx-Pro-containing Aza-peptides</title><pii><json:string>0040-4039(95)02124-8</json:string></pii><genre><json:string>research-article</json:string></genre><serie><title>Chemistry and Biochemistry of Amino Acids, Peptides and Proteins</title><language><json:string>unknown</json:string></language><volume>Vol. 7</volume><pages><first>267</first><last>357</last></pages><editor><json:item><name>B. 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We propose triphosgene as a carbonylating agent for coupling the properly substituted hydrazide to the proline nitrogen to obtain the AzAsx-Pro or AzAla-Pro aza-sequence (Az denotes the N CαH replacement, and Asx stands for Asn or Asp). The structure of three Z-AzAsx-Pro-NHiPr and of the Boc-AzAla-Pro-NHiPr aza dipeptides has been studied in solution by 1H-NMR and IR spectroscopy, and three of them have been investigated in the crystalline state by X-ray diffraction.</p></abstract><abstract style="graphical"><p>Triphosgene is a convenient carbonylating agent for the synthesis of AzAsx-Pro-containing azadipeptides which accommodate a βll'-like folded structure in both solution and crystalline state.gr1</p></abstract></profileDesc><revisionDesc><change when="1995">Published</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/document/6F33326EE98EC3ED18CDB5FED0348D4A132A00FB/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Elsevier, elements deleted: tail"><istex:xmlDeclaration>version="1.0" encoding="utf-8"</istex:xmlDeclaration><istex:docType PUBLIC="-//ES//DTD journal article DTD version 4.5.2//EN//XML" URI="art452.dtd" name="istex:docType"><istex:entity SYSTEM="gr1" NDATA="IMAGE" name="gr1"></istex:entity></istex:docType><istex:document><converted-article version="4.5.2" docsubtype="fla"><item-info><jid>TETL</jid><aid>95021248</aid><ce:pii>0040-4039(95)02124-8</ce:pii><ce:doi>10.1016/0040-4039(95)02124-8</ce:doi><ce:copyright type="unknown" year="1995"></ce:copyright></item-info><head><ce:title>Synthesis and structure of AzAsx-Pro-containing Aza-peptides</ce:title><ce:author-group><ce:author><ce:given-name>Frédéric</ce:given-name><ce:surname>André</ce:surname></ce:author><ce:author><ce:given-name>Michel</ce:given-name><ce:surname>Marraud</ce:surname></ce:author><ce:author><ce:given-name>Guy</ce:given-name><ce:surname>Boussard</ce:surname><ce:ranking><ce:sup>∗</ce:sup></ce:ranking></ce:author><ce:affiliation><ce:textfn>Laboratoire de Chimie Physique Macromoléculaire, associé au CNRS, ENSIC-INPL, BP 451, 54001 Nancy, France</ce:textfn></ce:affiliation></ce:author-group><ce:author-group><ce:author><ce:given-name>Claude</ce:given-name><ce:surname>Didierjean</ce:surname></ce:author><ce:author><ce:given-name>André</ce:given-name><ce:surname>Aubry</ce:surname></ce:author><ce:affiliation><ce:textfn>Laboratoire de Cristallographie et Modélisation des Matériaux Minéraux et Biologiques, associé au CNRS, Université de Nancy I, BP 239, 54506 Vandoeuvre, France</ce:textfn></ce:affiliation></ce:author-group><ce:date-received day="13" month="10" year="1995"></ce:date-received><ce:date-accepted day="2" month="11" year="1995"></ce:date-accepted><ce:abstract><ce:section-title>Abstract</ce:section-title><ce:abstract-sec><ce:simple-para>One possible α-modification in peptides is the substitution of a nitrogen for the C<ce:sup>α</ce:sup>H group. We propose triphosgene as a carbonylating agent for coupling the properly substituted hydrazide to the proline nitrogen to obtain the AzAsx-Pro or AzAla-Pro aza-sequence (Az denotes the <math altimg="si1.gif"><fr shape="sol"><nu>N</nu><de>C<sup>α</sup>H</de></fr></math> replacement, and Asx stands for Asn or Asp). The structure of three Z-AzAsx-Pro-NH<ce:sup>i</ce:sup>Pr and of the Boc-AzAla-Pro-NH<ce:sup>i</ce:sup>Pr aza dipeptides has been studied in solution by <ce:sup loc="pre">1</ce:sup>H-NMR and IR spectroscopy, and three of them have been investigated in the crystalline state by X-ray diffraction.</ce:simple-para></ce:abstract-sec></ce:abstract><ce:abstract class="graphical"><ce:abstract-sec><ce:simple-para>Triphosgene is a convenient carbonylating agent for the synthesis of AzAsx-Pro-containing azadipeptides which accommodate a βll'-like folded structure in both solution and crystalline state.</ce:simple-para></ce:abstract-sec><ce:figure><ce:link locator="gr1"></ce:link></ce:figure></ce:abstract></head></converted-article></istex:document></istex:metadataXml><mods version="3.6"><titleInfo><title>Synthesis and structure of AzAsx-Pro-containing Aza-peptides</title></titleInfo><titleInfo type="alternative" contentType="CDATA"><title>Synthesis and structure of AzAsx-Pro-containing Aza-peptides</title></titleInfo><name type="personal"><namePart type="given">Frédéric</namePart><namePart type="family">André</namePart><affiliation>Laboratoire de Chimie Physique Macromoléculaire, associé au CNRS, ENSIC-INPL, BP 451, 54001 Nancy, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Michel</namePart><namePart type="family">Marraud</namePart><affiliation>Laboratoire de Chimie Physique Macromoléculaire, associé au CNRS, ENSIC-INPL, BP 451, 54001 Nancy, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Guy</namePart><namePart type="family">Boussard</namePart><affiliation>Laboratoire de Chimie Physique Macromoléculaire, associé au CNRS, ENSIC-INPL, BP 451, 54001 Nancy, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Claude</namePart><namePart type="family">Didierjean</namePart><affiliation>Laboratoire de Cristallographie et Modélisation des Matériaux Minéraux et Biologiques, associé au CNRS, Université de Nancy I, BP 239, 54506 Vandoeuvre, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">André</namePart><namePart type="family">Aubry</namePart><affiliation>Laboratoire de Cristallographie et Modélisation des Matériaux Minéraux et Biologiques, associé au CNRS, Université de Nancy I, BP 239, 54506 Vandoeuvre, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="research-article" displayLabel="Full-length article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-1JC4F85T-7">research-article</genre><originInfo><publisher>ELSEVIER</publisher><dateIssued encoding="w3cdtf">1995</dateIssued><copyrightDate encoding="w3cdtf">1995</copyrightDate></originInfo><language><languageTerm type="code" authority="iso639-2b">eng</languageTerm><languageTerm type="code" authority="rfc3066">en</languageTerm></language><abstract lang="en">Abstract: One possible α-modification in peptides is the substitution of a nitrogen for the CαH group. We propose triphosgene as a carbonylating agent for coupling the properly substituted hydrazide to the proline nitrogen to obtain the AzAsx-Pro or AzAla-Pro aza-sequence (Az denotes the N CαH replacement, and Asx stands for Asn or Asp). The structure of three Z-AzAsx-Pro-NHiPr and of the Boc-AzAla-Pro-NHiPr aza dipeptides has been studied in solution by 1H-NMR and IR spectroscopy, and three of them have been investigated in the crystalline state by X-ray diffraction.</abstract><abstract type="graphical">Triphosgene is a convenient carbonylating agent for the synthesis of AzAsx-Pro-containing azadipeptides which accommodate a βll'-like folded structure in both solution and crystalline state.gr1 </abstract><relatedItem type="host"><titleInfo><title>Tetrahedron Letters</title></titleInfo><titleInfo type="abbreviated"><title>TETL</title></titleInfo><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><originInfo><publisher>ELSEVIER</publisher><dateIssued encoding="w3cdtf">19960108</dateIssued></originInfo><identifier type="ISSN">0040-4039</identifier><identifier type="PII">S0040-4039(00)X0029-9</identifier><part><date>19960108</date><detail type="volume"><number>37</number><caption>vol.</caption></detail><detail type="issue"><number>2</number><caption>no.</caption></detail><extent unit="issue-pages"><start>139</start><end>278</end></extent><extent unit="pages"><start>183</start><end>186</end></extent></part></relatedItem><identifier type="istex">6F33326EE98EC3ED18CDB5FED0348D4A132A00FB</identifier><identifier type="ark">ark:/67375/6H6-0QTLSK07-S</identifier><identifier type="DOI">10.1016/0040-4039(95)02124-8</identifier><identifier type="PII">0040-4039(95)02124-8</identifier><recordInfo><recordContentSource authority="ISTEX" authorityURI="https://loaded-corpus.data.istex.fr" valueURI="https://loaded-corpus.data.istex.fr/ark:/67375/XBH-HKKZVM7B-M">elsevier</recordContentSource></recordInfo></mods><json:item><extension>json</extension><original>false</original><mimetype>application/json</mimetype><uri>https://api.istex.fr/document/6F33326EE98EC3ED18CDB5FED0348D4A132A00FB/metadata/json</uri></json:item></metadata></istex></record>Pour manipuler ce document sous Unix (Dilib)
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