Synthesis and Characterization of Polyrotaxane−Amino Acid Conjugates: A New Synthetic Pathway for Amino-Functionalized Polyrotaxanes
Novel polyrotaxane conjugates possessing side chains of protected amino acids, that is, N α-tert-butyloxycarbonylglycine (Boc-Gly) and N α-benzyloxycarbonylglycine (Z-Gly), were successfully prepared via the carbonyldiimidazole-mediated esterification of hydroxyl groups in a polyrotaxane. The prepar...
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| Veröffentlicht in: | Biomacromolecules 2009-07, Vol.10 (7), p.1947-1954 |
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| container_end_page | 1954 |
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| container_issue | 7 |
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| container_title | Biomacromolecules |
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| creator | Araki, Jun Kagaya, Keisuke Ohkawa, Kousaku |
| description | Novel polyrotaxane conjugates possessing side chains of protected amino acids, that is, N α-tert-butyloxycarbonylglycine (Boc-Gly) and N α-benzyloxycarbonylglycine (Z-Gly), were successfully prepared via the carbonyldiimidazole-mediated esterification of hydroxyl groups in a polyrotaxane. The prepared conjugates were soluble in a wide variety of organic solvents, including N,N-dimethylacetamide, N,N-dimethylformamide, tetrahydrofuran, pyridine, and methanol. Thermogravimetric measurements of the conjugates showed three-step decomposition curves corresponding to the decompositions of the amino acid, poly(ethylene glycol) axis, and cyclodextrin rings. The Z-Gly−polyrotaxane conjugate showed a remarkable exotherm at 334 °C, together with a large weight loss. Treatment of the Boc-Gly−polyrotaxane conjugate with neat trifluoroacetic acid resulted in the complete removal of the Boc groups and gave a cationic polyrotaxane with many free primary amino groups, the amount of which was determined by colloidal titrations. |
| doi_str_mv | 10.1021/bm900343y |
| format | Article |
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The prepared conjugates were soluble in a wide variety of organic solvents, including N,N-dimethylacetamide, N,N-dimethylformamide, tetrahydrofuran, pyridine, and methanol. Thermogravimetric measurements of the conjugates showed three-step decomposition curves corresponding to the decompositions of the amino acid, poly(ethylene glycol) axis, and cyclodextrin rings. The Z-Gly−polyrotaxane conjugate showed a remarkable exotherm at 334 °C, together with a large weight loss. 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The prepared conjugates were soluble in a wide variety of organic solvents, including N,N-dimethylacetamide, N,N-dimethylformamide, tetrahydrofuran, pyridine, and methanol. Thermogravimetric measurements of the conjugates showed three-step decomposition curves corresponding to the decompositions of the amino acid, poly(ethylene glycol) axis, and cyclodextrin rings. The Z-Gly−polyrotaxane conjugate showed a remarkable exotherm at 334 °C, together with a large weight loss. Treatment of the Boc-Gly−polyrotaxane conjugate with neat trifluoroacetic acid resulted in the complete removal of the Boc groups and gave a cationic polyrotaxane with many free primary amino groups, the amount of which was determined by colloidal titrations.</description><subject>Amino Acids - chemistry</subject><subject>Applied sciences</subject><subject>Chemical modifications</subject><subject>Chemical reactions and properties</subject><subject>Colloids</subject><subject>Drug Stability</subject><subject>Exact sciences and technology</subject><subject>Formic Acid Esters</subject><subject>Hot Temperature</subject><subject>Organic polymers</subject><subject>Physicochemistry of polymers</subject><subject>Rotaxanes - chemical synthesis</subject><subject>Rotaxanes - chemistry</subject><subject>Solubility</subject><issn>1525-7797</issn><issn>1526-4602</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0c1qFTEYBuBQlP7pojcg2Yh0MTb_M-PucGhVKLagrodvMklPDjOTmmSo0wsorr1Er8S053BEECSLZPHkTfhehE4oeUsJo2ftUBPCBZ_30CGVTBVCEfbs6SyLsqzLA3QU45oQUnMh99EBraWQlPFD9PB5HtPKRBcxjB1eriCATia4e0jOj9hbfO37OfgE32E0v378XAxu9HihXdZ-XE83kEx8hxf4k7nDm7TkNL6GtLqDGVsf8NOV4mIa9WMm9O7edH_FxhfouYU-mpfb_Rh9vTj_svxQXF69_7hcXBYgBEtFZ9uqtFa1ylpNBO9UzQyrpaKstZXpDFNW26rktgbbKqK1pdpom0XJ27yO0ZtN7m3w3yYTUzO4qE3f50_4KTYVY1IKLvl_ZZknKKr8cJanG6mDjzEY29wGN0CYG0qax36aXT_ZvtqmTu1guj9yW0gGr7cAoobeBhi1izvHGFF1mWvcOdCxWfsp5LHGfzz4G7xuqEU</recordid><startdate>20090713</startdate><enddate>20090713</enddate><creator>Araki, Jun</creator><creator>Kagaya, Keisuke</creator><creator>Ohkawa, Kousaku</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20090713</creationdate><title>Synthesis and Characterization of Polyrotaxane−Amino Acid Conjugates: A New Synthetic Pathway for Amino-Functionalized Polyrotaxanes</title><author>Araki, Jun ; Kagaya, Keisuke ; Ohkawa, Kousaku</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a442t-dfb87ff6b6ffc043d692e295612bf8ede26fcf873f9afb60ccf1cecf95673b3b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Amino Acids - chemistry</topic><topic>Applied sciences</topic><topic>Chemical modifications</topic><topic>Chemical reactions and properties</topic><topic>Colloids</topic><topic>Drug Stability</topic><topic>Exact sciences and technology</topic><topic>Formic Acid Esters</topic><topic>Hot Temperature</topic><topic>Organic polymers</topic><topic>Physicochemistry of polymers</topic><topic>Rotaxanes - chemical synthesis</topic><topic>Rotaxanes - chemistry</topic><topic>Solubility</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Araki, Jun</creatorcontrib><creatorcontrib>Kagaya, Keisuke</creatorcontrib><creatorcontrib>Ohkawa, Kousaku</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Biomacromolecules</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Araki, Jun</au><au>Kagaya, Keisuke</au><au>Ohkawa, Kousaku</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Characterization of Polyrotaxane−Amino Acid Conjugates: A New Synthetic Pathway for Amino-Functionalized Polyrotaxanes</atitle><jtitle>Biomacromolecules</jtitle><addtitle>Biomacromolecules</addtitle><date>2009-07-13</date><risdate>2009</risdate><volume>10</volume><issue>7</issue><spage>1947</spage><epage>1954</epage><pages>1947-1954</pages><issn>1525-7797</issn><eissn>1526-4602</eissn><abstract>Novel polyrotaxane conjugates possessing side chains of protected amino acids, that is, N α-tert-butyloxycarbonylglycine (Boc-Gly) and N α-benzyloxycarbonylglycine (Z-Gly), were successfully prepared via the carbonyldiimidazole-mediated esterification of hydroxyl groups in a polyrotaxane. 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| ispartof | Biomacromolecules, 2009-07, Vol.10 (7), p.1947-1954 |
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| subjects | Amino Acids - chemistry Applied sciences Chemical modifications Chemical reactions and properties Colloids Drug Stability Exact sciences and technology Formic Acid Esters Hot Temperature Organic polymers Physicochemistry of polymers Rotaxanes - chemical synthesis Rotaxanes - chemistry Solubility |
| title | Synthesis and Characterization of Polyrotaxane−Amino Acid Conjugates: A New Synthetic Pathway for Amino-Functionalized Polyrotaxanes |
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