Polycondensation of activated L‐valine and L‐leucine esters with various lewis acids
Identifieur interne : 001520 ( Main/Curation ); précédent : 001519; suivant : 001521Polycondensation of activated L‐valine and L‐leucine esters with various lewis acids
Auteurs : Tadamasa Nemoto [Japon] ; Daisuke Ando [Japon] ; Kensuke Naka [Japon] ; Yoshiki Chujo [Japon]Source :
- Journal of Polymer Science Part A: Polymer Chemistry [ 0887-624X ] ; 2007-02-01.
Descripteurs français
- Wicri :
- topic : Polymère.
English descriptors
- KwdEn :
- Amino, Amino acid esters, Amino acids, Carbonyl, Carbonyl oxygen, Cation, Chem, Condensation reaction, Condensation reactions, Elution volume, Ester, Ftir, Ftir spectra, Hindrance, Isobutyl group, Isopropyl, Isopropyl group, Lewis acid, Lewis acids, Metal cation, Molecular weight, Naka, Nemoto, Peptide bonds, Polycondensation, Polym, Polym chem, Polymer, Polymer chemistry, Polymer science, Polymerization, Reaction mixture, Results show, Room temperature, Steric, Steric hindrance, Various kinds, Various metal, Wiley periodicals, Yttrium.
- Teeft :
- Amino, Amino acid esters, Amino acids, Carbonyl, Carbonyl oxygen, Cation, Chem, Condensation reaction, Condensation reactions, Elution volume, Ester, Ftir, Ftir spectra, Hindrance, Isobutyl group, Isopropyl, Isopropyl group, Lewis acid, Lewis acids, Metal cation, Molecular weight, Naka, Nemoto, Peptide bonds, Polycondensation, Polym, Polym chem, Polymer, Polymer chemistry, Polymer science, Polymerization, Reaction mixture, Results show, Room temperature, Steric, Steric hindrance, Various kinds, Various metal, Wiley periodicals, Yttrium.
Abstract
To develop a novel polycondensation method for the preparation of poly (amino acid)s, we screened a transition metal or a rare‐earth triflate as a Lewis acid for the polycondensation of activated amino acid esters in N,N‐dimethylformamide solutions at room temperature. The polymerizations of 4‐nitrophenyl L‐leucinate (1a) and 4‐nitrophenyl L‐valinate (1b) scarcely proceeded without any Lewis acid at room temperature. In the presence of 5 mol % metal triflates, especially scandium(III) trifluoromethanesulfonate, the polymerizations of both monomers were promoted effectively. The products, which were collected by the reaction mixture being poured into water, were recognized as poly(L‐valine)s by Fourier transform infrared spectroscopy, gel permeation chromatography analysis, and 1H NMR spectroscopy. These results showed that a metal triflate as a Lewis acid could coordinate to a carbonyl oxygen of activated L‐valinate and L‐leucinate even in a highly polar solvent, such as N,N‐dimethylformamide; therefore, the polymerizations of activated L‐valinate and L‐leucinate were promoted. Because steric hindrance derived from the isobutyl group in 1b was less than that of the isopropyl unit in 1a, the effect of the metals was not as sensitive for the polymerization of 1b. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 543–547, 2007
Url:
DOI: 10.1002/pola.21895
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Nemoto</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo‐Ku, Kyoto 615‐8510</wicri:regionArea><orgName type="university">Université de Kyoto</orgName><placeName><settlement type="city">Kyoto</settlement><region type="prefecture">Région du Kansai</region></placeName></affiliation></author><author><name sortKey="Ando, Daisuke" sort="Ando, Daisuke" uniqKey="Ando D" first="Daisuke" last="Ando">Daisuke Ando</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo‐Ku, Kyoto 615‐8510</wicri:regionArea><orgName type="university">Université de Kyoto</orgName><placeName><settlement type="city">Kyoto</settlement><region type="prefecture">Région du Kansai</region></placeName></affiliation></author><author><name sortKey="Naka, Kensuke" sort="Naka, Kensuke" uniqKey="Naka K" first="Kensuke" last="Naka">Kensuke Naka</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo‐Ku, Kyoto 615‐8510</wicri:regionArea><orgName type="university">Université de Kyoto</orgName><placeName><settlement type="city">Kyoto</settlement><region type="prefecture">Région du Kansai</region></placeName></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Japon</country></affiliation><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Correspondence address: Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo‐Ku, Kyoto 615‐8510</wicri:regionArea><orgName type="university">Université de Kyoto</orgName><placeName><settlement type="city">Kyoto</settlement><region type="prefecture">Région du Kansai</region></placeName></affiliation></author><author><name sortKey="Chujo, Yoshiki" sort="Chujo, Yoshiki" uniqKey="Chujo Y" first="Yoshiki" last="Chujo">Yoshiki Chujo</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo‐Ku, Kyoto 615‐8510</wicri:regionArea><orgName type="university">Université de Kyoto</orgName><placeName><settlement type="city">Kyoto</settlement><region type="prefecture">Région du Kansai</region></placeName></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Journal of Polymer Science Part A: Polymer Chemistry</title><title level="j" type="alt">JOURNAL OF POLYMER SCIENCE PART A: POLYMER CHEMISTRY</title><idno type="ISSN">0887-624X</idno><idno type="eISSN">1099-0518</idno><imprint><biblScope unit="vol">45</biblScope><biblScope unit="issue">3</biblScope><biblScope unit="page" from="543">543</biblScope><biblScope unit="page" to="547">547</biblScope><biblScope unit="page-count">5</biblScope><publisher>Wiley Subscription Services, Inc., A Wiley Company</publisher><pubPlace>Hoboken</pubPlace><date type="published" when="2007-02-01">2007-02-01</date></imprint><idno type="ISSN">0887-624X</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0887-624X</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amino</term><term>Amino acid esters</term><term>Amino acids</term><term>Carbonyl</term><term>Carbonyl oxygen</term><term>Cation</term><term>Chem</term><term>Condensation reaction</term><term>Condensation reactions</term><term>Elution volume</term><term>Ester</term><term>Ftir</term><term>Ftir spectra</term><term>Hindrance</term><term>Isobutyl group</term><term>Isopropyl</term><term>Isopropyl group</term><term>Lewis acid</term><term>Lewis acids</term><term>Metal cation</term><term>Molecular weight</term><term>Naka</term><term>Nemoto</term><term>Peptide bonds</term><term>Polycondensation</term><term>Polym</term><term>Polym chem</term><term>Polymer</term><term>Polymer chemistry</term><term>Polymer science</term><term>Polymerization</term><term>Reaction mixture</term><term>Results show</term><term>Room temperature</term><term>Steric</term><term>Steric hindrance</term><term>Various kinds</term><term>Various metal</term><term>Wiley periodicals</term><term>Yttrium</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>Amino</term><term>Amino acid esters</term><term>Amino acids</term><term>Carbonyl</term><term>Carbonyl oxygen</term><term>Cation</term><term>Chem</term><term>Condensation reaction</term><term>Condensation reactions</term><term>Elution volume</term><term>Ester</term><term>Ftir</term><term>Ftir spectra</term><term>Hindrance</term><term>Isobutyl group</term><term>Isopropyl</term><term>Isopropyl group</term><term>Lewis acid</term><term>Lewis acids</term><term>Metal cation</term><term>Molecular weight</term><term>Naka</term><term>Nemoto</term><term>Peptide bonds</term><term>Polycondensation</term><term>Polym</term><term>Polym chem</term><term>Polymer</term><term>Polymer chemistry</term><term>Polymer science</term><term>Polymerization</term><term>Reaction mixture</term><term>Results show</term><term>Room temperature</term><term>Steric</term><term>Steric hindrance</term><term>Various kinds</term><term>Various metal</term><term>Wiley periodicals</term><term>Yttrium</term></keywords><keywords scheme="Wicri" type="topic" xml:lang="fr"><term>Polymère</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract">To develop a novel polycondensation method for the preparation of poly (amino acid)s, we screened a transition metal or a rare‐earth triflate as a Lewis acid for the polycondensation of activated amino acid esters in N,N‐dimethylformamide solutions at room temperature. The polymerizations of 4‐nitrophenyl L‐leucinate (1a) and 4‐nitrophenyl L‐valinate (1b) scarcely proceeded without any Lewis acid at room temperature. In the presence of 5 mol % metal triflates, especially scandium(III) trifluoromethanesulfonate, the polymerizations of both monomers were promoted effectively. The products, which were collected by the reaction mixture being poured into water, were recognized as poly(L‐valine)s by Fourier transform infrared spectroscopy, gel permeation chromatography analysis, and 1H NMR spectroscopy. These results showed that a metal triflate as a Lewis acid could coordinate to a carbonyl oxygen of activated L‐valinate and L‐leucinate even in a highly polar solvent, such as N,N‐dimethylformamide; therefore, the polymerizations of activated L‐valinate and L‐leucinate were promoted. Because steric hindrance derived from the isobutyl group in 1b was less than that of the isopropyl unit in 1a, the effect of the metals was not as sensitive for the polymerization of 1b. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 543–547, 2007</div></front></TEI></record>Pour manipuler ce document sous Unix (Dilib)
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