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<identifier>oai:HAL:hal-01091920v1</identifier>
<datestamp>2018-01-11</datestamp>
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<setSpec>subject:chim</setSpec>
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<publisher>HAL CCSD</publisher>
<title lang=en>Glaser oxidative coupling on peptides: Stabilization of β-turn structure via a 1,3-butadiyne constraint.</title>
<creator>Auberger, Nicolas</creator>
<creator>Pisa, Margherita Di</creator>
<creator>Larregola, Maud</creator>
<creator>Chassaing, Gérard</creator>
<creator>Peroni, Elisa</creator>
<creator>Lavielle, Solange</creator>
<creator>Papini, Anna-Maria</creator>
<creator>Lequin, Olivier</creator>
<creator>Mallet, Jean-Maurice</creator>
<contributor>Chimie Organique (UCO) ; Institut Pasteur [Paris] - Centre National de la Recherche Scientifique (CNRS)</contributor>
<contributor>Université Pierre et Marie Curie - Paris 6 (UPMC)</contributor>
<contributor>Department of Organic Chemistry Ugo Schiff and CNR ICCOM ; University of Florence</contributor>
<contributor>Synthèse, Structure et Fonction de Molécules Bioactives (SSFMB) ; Université Pierre et Marie Curie - Paris 6 (UPMC) - Centre National de la Recherche Scientifique (CNRS)</contributor>
<contributor>Dynamique des écosystèmes Caraïbe et biologie des espèces associées (DYNECAR EA 926) ; Université des Antilles et de la Guyane (UAG)</contributor>
<description>International audience</description>
<source>Bioorganic and Medicinal Chemistry</source>
<identifier>hal-01091920</identifier>
<identifier>https://hal.archives-ouvertes.fr/hal-01091920</identifier>
<source>https://hal.archives-ouvertes.fr/hal-01091920</source>
<source>Bioorganic and Medicinal Chemistry, 2014, 22 (24), pp.6924-6932. 〈10.1016/j.bmc.2014.10.026〉</source>
<identifier>PUBMED : 25456082</identifier>
<relation>info:eu-repo/semantics/altIdentifier/pmid/25456082</relation>
<identifier>DOI : 10.1016/j.bmc.2014.10.026</identifier>
<relation>info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmc.2014.10.026</relation>
<language>en</language>
<subject>[CHIM.ORGA] Chemical Sciences/Organic chemistry</subject>
<type>info:eu-repo/semantics/article</type>
<type>Journal articles</type>
<description lang=en>The Glaser-Eglinton reaction between either two C or N propargylglycine (Pra or NPra) amino acids, in the presence of copper(II), led to cyclic hexa- and octapeptides constrained by a butadiyne bridge. The on-resin cyclization conditions were analyzed and optimized. The consequences of this type of constraint on the three dimensional structure of these hexapeptides and octapeptides were analyzed in details by NMR and molecular dynamics. We show that stabilized short cyclic peptides could be readily prepared via the Glaser oxidative coupling either with a chiral (Pra), or achiral (NPra) residue. The 1,3-butadiyne cyclization, along with disulfide bridged and lactam cyclized hexapeptides expands the range of constrained peptides that will allow exploring the breathing of amino acids around a β-turn structure.</description>
<date>2014-12-15</date>
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