Straightforward synthesis of non-natural chalcogen peptides via ring opening of aziridines
Identifieur interne : 001514 ( Main/Repository ); précédent : 001513; suivant : 001515Straightforward synthesis of non-natural chalcogen peptides via ring opening of aziridines
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Abstract
The synthesis of new chiral non-natural seleno-, thio-, and telluro-peptides is described herein. These new compounds were prepared through simple and brief synthetic route, from inexpensive and commercially available amino acids. The products, possessing a highly modular character, were obtained in good to excellent yields (50-96%), via ring opening of aziridines with chalcogenolate anions, generated using indium(I) iodide as a reducing agent.
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en" level="a">Straightforward synthesis of non-natural chalcogen peptides via ring opening of aziridines</title><author><name sortKey="Schwab, Ricardo S" uniqKey="Schwab R">Ricardo S. Schwab</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Instituto de Química, Universidade Federal do Rio Grande do Sul, UFRGS</s1><s2>C.P. 15003, 91501-970 Porto Alegre-RS</s2><s3>BRA</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ></inist:fA14><country>Brésil</country><wicri:noRegion>C.P. 15003, 91501-970 Porto Alegre-RS</wicri:noRegion></affiliation></author><author><name sortKey="Schneider, Paulo H" uniqKey="Schneider P">Paulo H. Schneider</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Instituto de Química, Universidade Federal do Rio Grande do Sul, UFRGS</s1><s2>C.P. 15003, 91501-970 Porto Alegre-RS</s2><s3>BRA</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ></inist:fA14><country>Brésil</country><wicri:noRegion>C.P. 15003, 91501-970 Porto Alegre-RS</wicri:noRegion></affiliation></author></titleStmt><publicationStmt><idno type="inist">13-0029817</idno><date when="2012">2012</date><idno type="stanalyst">PASCAL 13-0029817 INIST</idno><idno type="RBID">Pascal:13-0029817</idno><idno type="wicri:Area/Main/Corpus">001425</idno><idno type="wicri:Area/Main/Repository">001514</idno></publicationStmt><seriesStmt><idno type="ISSN">0040-4020</idno><title level="j" type="abbreviated">Tetrahedron : (Oxf. Print)</title><title level="j" type="main">Tetrahedron : (Oxford. Print)</title></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aminoacid</term><term>Anions</term><term>Aziridine derivatives</term><term>Chalcogen</term><term>Chemical synthesis</term><term>Chiral compound</term><term>Indium iodide</term><term>Nitrogen heterocycle</term><term>Organic selenide</term><term>Organic sulfide</term><term>Organic telluride</term><term>Peptides</term><term>Reducing agent</term><term>Ring cleavage</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Synthèse chimique</term><term>Chalcogène</term><term>Peptide</term><term>Décyclisation</term><term>Dérivé de l'aziridine</term><term>Composé chiral</term><term>Séléniure organique</term><term>Sulfure organique</term><term>Tellurure organique</term><term>Aminoacide</term><term>Anion</term><term>Iodure d'indium</term><term>Réducteur</term><term>Hétérocycle azote</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The synthesis of new chiral non-natural seleno-, thio-, and telluro-peptides is described herein. These new compounds were prepared through simple and brief synthetic route, from inexpensive and commercially available amino acids. The products, possessing a highly modular character, were obtained in good to excellent yields (50-96%), via ring opening of aziridines with chalcogenolate anions, generated using indium(I) iodide as a reducing agent.</div></front></TEI><inist><standard h6="B"><pA><fA01 i1="01" i2="1"><s0>0040-4020</s0></fA01><fA02 i1="01"><s0>TETRAB</s0></fA02><fA03 i2="1"><s0>Tetrahedron : (Oxf. Print)</s0></fA03><fA05><s2>68</s2></fA05><fA06><s2>51</s2></fA06><fA08 i1="01" i2="1" l="ENG"><s1>Straightforward synthesis of non-natural chalcogen peptides via ring opening of aziridines</s1></fA08><fA09 i1="01" i2="1" l="ENG"><s1>Progress in Organoselenium and Organotellurium Chemistry</s1></fA09><fA11 i1="01" i2="1"><s1>SCHWAB (Ricardo S.)</s1></fA11><fA11 i1="02" i2="1"><s1>SCHNEIDER (Paulo H.)</s1></fA11><fA12 i1="01" i2="1"><s1>ZENI (G.)</s1><s9>ed.</s9></fA12><fA12 i1="02" i2="1"><s1>LENARDAO (E. J.)</s1><s9>ed.</s9></fA12><fA14 i1="01"><s1>Instituto de Química, Universidade Federal do Rio Grande do Sul, UFRGS</s1><s2>C.P. 15003, 91501-970 Porto Alegre-RS</s2><s3>BRA</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ></fA14><fA15 i1="01"><s1>Laboratório de Síntese, Reatividade, Avaliação Farmacológica e Toxicológica de Organocalcogênios, CCNE, UFSM</s1><s2>Santa Maria 97105-900, RS</s2><s3>BRA</s3><sZ>1 aut.</sZ></fA15><fA15 i1="02"><s1>Laboratorio de Sintese Orgànica Limpa-LASOL-CCQFA, Universidade Federal de Pelotas, P.O. Box 354</s1><s2>Pelotas 96010-900, RS</s2><s3>BRA</s3><sZ>2 aut.</sZ></fA15><fA20><s2>10393, 10449-10455 [8 p.]</s2></fA20><fA21><s1>2012</s1></fA21><fA23 i1="01"><s0>ENG</s0></fA23><fA43 i1="01"><s1>INIST</s1><s2>8899</s2><s5>354000506867250080</s5></fA43><fA44><s0>0000</s0><s1>© 2013 INIST-CNRS. All rights reserved.</s1></fA44><fA45><s0>26 ref.</s0></fA45><fA47 i1="01" i2="1"><s0>13-0029817</s0></fA47><fA60><s1>P</s1></fA60><fA61><s0>A</s0></fA61><fA64 i1="01" i2="1"><s0>Tetrahedron : (Oxford. Print)</s0></fA64><fA66 i1="01"><s0>GBR</s0></fA66><fC01 i1="01" l="ENG"><s0>The synthesis of new chiral non-natural seleno-, thio-, and telluro-peptides is described herein. These new compounds were prepared through simple and brief synthetic route, from inexpensive and commercially available amino acids. The products, possessing a highly modular character, were obtained in good to excellent yields (50-96%), via ring opening of aziridines with chalcogenolate anions, generated using indium(I) iodide as a reducing agent.</s0></fC01><fC02 i1="01" i2="X"><s0>001C03C08</s0></fC02><fC02 i1="02" i2="X"><s0>001C03C06B</s0></fC02><fC03 i1="01" i2="X" l="FRE"><s0>Synthèse chimique</s0><s5>01</s5></fC03><fC03 i1="01" i2="X" l="ENG"><s0>Chemical synthesis</s0><s5>01</s5></fC03><fC03 i1="01" i2="X" l="SPA"><s0>Síntesis química</s0><s5>01</s5></fC03><fC03 i1="02" i2="X" l="FRE"><s0>Chalcogène</s0><s2>NC</s2><s5>02</s5></fC03><fC03 i1="02" i2="X" l="ENG"><s0>Chalcogen</s0><s2>NC</s2><s5>02</s5></fC03><fC03 i1="02" i2="X" l="SPA"><s0>Calcógeno</s0><s2>NC</s2><s5>02</s5></fC03><fC03 i1="03" i2="X" l="FRE"><s0>Peptide</s0><s5>03</s5></fC03><fC03 i1="03" i2="X" l="ENG"><s0>Peptides</s0><s5>03</s5></fC03><fC03 i1="03" i2="X" l="SPA"><s0>Péptido</s0><s5>03</s5></fC03><fC03 i1="04" i2="X" l="FRE"><s0>Décyclisation</s0><s5>04</s5></fC03><fC03 i1="04" i2="X" l="ENG"><s0>Ring cleavage</s0><s5>04</s5></fC03><fC03 i1="04" i2="X" l="SPA"><s0>Desciclización</s0><s5>04</s5></fC03><fC03 i1="05" i2="X" l="FRE"><s0>Dérivé de l'aziridine</s0><s2>FR</s2><s5>05</s5></fC03><fC03 i1="05" i2="X" l="ENG"><s0>Aziridine derivatives</s0><s2>FR</s2><s5>05</s5></fC03><fC03 i1="06" i2="X" l="FRE"><s0>Composé chiral</s0><s5>06</s5></fC03><fC03 i1="06" i2="X" l="ENG"><s0>Chiral compound</s0><s5>06</s5></fC03><fC03 i1="06" i2="X" l="SPA"><s0>Compuesto quiral</s0><s5>06</s5></fC03><fC03 i1="07" i2="X" l="FRE"><s0>Séléniure organique</s0><s5>07</s5></fC03><fC03 i1="07" i2="X" l="ENG"><s0>Organic selenide</s0><s5>07</s5></fC03><fC03 i1="07" i2="X" l="SPA"><s0>Seleniuro orgánico</s0><s5>07</s5></fC03><fC03 i1="08" i2="X" l="FRE"><s0>Sulfure organique</s0><s5>08</s5></fC03><fC03 i1="08" i2="X" l="ENG"><s0>Organic sulfide</s0><s5>08</s5></fC03><fC03 i1="08" i2="X" l="SPA"><s0>Sulfuro orgánico</s0><s5>08</s5></fC03><fC03 i1="09" i2="X" l="FRE"><s0>Tellurure organique</s0><s5>09</s5></fC03><fC03 i1="09" i2="X" l="ENG"><s0>Organic telluride</s0><s5>09</s5></fC03><fC03 i1="09" i2="X" l="SPA"><s0>Telururo orgánico</s0><s5>09</s5></fC03><fC03 i1="10" i2="X" l="FRE"><s0>Aminoacide</s0><s5>10</s5></fC03><fC03 i1="10" i2="X" l="ENG"><s0>Aminoacid</s0><s5>10</s5></fC03><fC03 i1="10" i2="X" l="SPA"><s0>Aminoácido</s0><s5>10</s5></fC03><fC03 i1="11" i2="X" l="FRE"><s0>Anion</s0><s2>NA</s2><s5>11</s5></fC03><fC03 i1="11" i2="X" l="ENG"><s0>Anions</s0><s2>NA</s2><s5>11</s5></fC03><fC03 i1="11" i2="X" l="SPA"><s0>Anión</s0><s2>NA</s2><s5>11</s5></fC03><fC03 i1="12" i2="X" l="FRE"><s0>Iodure d'indium</s0><s5>12</s5></fC03><fC03 i1="12" i2="X" l="ENG"><s0>Indium iodide</s0><s5>12</s5></fC03><fC03 i1="12" i2="X" l="SPA"><s0>Indio ioduro</s0><s5>12</s5></fC03><fC03 i1="13" i2="X" l="FRE"><s0>Réducteur</s0><s5>13</s5></fC03><fC03 i1="13" i2="X" l="ENG"><s0>Reducing agent</s0><s5>13</s5></fC03><fC03 i1="13" i2="X" l="SPA"><s0>Reductor</s0><s5>13</s5></fC03><fC03 i1="14" i2="X" l="FRE"><s0>Hétérocycle azote</s0><s5>41</s5></fC03><fC03 i1="14" i2="X" l="ENG"><s0>Nitrogen heterocycle</s0><s5>41</s5></fC03><fC03 i1="14" i2="X" l="SPA"><s0>Heterociclo nitrógeno</s0><s5>41</s5></fC03><fN21><s1>014</s1></fN21><fN44 i1="01"><s1>OTO</s1></fN44><fN82><s1>OTO</s1></fN82></pA></standard></inist></record>Pour manipuler ce document sous Unix (Dilib)
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