Preparation of a C6 quaternary ammonium chitosan derivative through a chitosan schiff base with click chemistry
In this study, we explored a new method for preparing C6 quaternary ammonium chitosan (CTS) derivatives. The C2NH2 of CTS was first protected by benzaldehyde. The C6OH of CTS was then transformed into a sulfonyl ester, which was then reacted with NaN3 through nucleophilic substitution to introduce...
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| Veröffentlicht in: | Journal of applied polymer science 2013-09, Vol.129 (6), p.3185-3191 |
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| container_issue | 6 |
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| container_title | Journal of applied polymer science |
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| creator | Chen, Yu Wang, Fengju Yun, Dongran Guo, Yanwen Ye, Yanchun Wang, Yanxi Tan, Huimin |
| description | In this study, we explored a new method for preparing C6 quaternary ammonium chitosan (CTS) derivatives. The C2NH2 of CTS was first protected by benzaldehyde. The C6OH of CTS was then transformed into a sulfonyl ester, which was then reacted with NaN3 through nucleophilic substitution to introduce the N3 group at the CTS C6 position. This intermediate was reacted in a click chemistry reaction with a terminal alkynyl quaternary ammonium salt; this was followed by the deprotection of C2NH2 with acid to furnish the C6 quaternary ammonium CTS derivative. The structures and properties of synthesized products in the reactions were characterized by Fourier transform infrared spectroscopy, NMR, X‐ray diffraction, and thermogravimetric analysis, respectively. The effects of the reaction conditions on the degree of Schiff‐base CTS quaternization were evaluated by elemental analysis. The largest inhibition zone test and the minimum inhibitory concentration test showed that compared with CTS, the prepared CTS derivative had significantly improved antibacterial activity toward Staphylococcus aureus and Escherichia coli. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013 |
| doi_str_mv | 10.1002/app.38431 |
| format | Article |
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The C2NH2 of CTS was first protected by benzaldehyde. The C6OH of CTS was then transformed into a sulfonyl ester, which was then reacted with NaN3 through nucleophilic substitution to introduce the N3 group at the CTS C6 position. This intermediate was reacted in a click chemistry reaction with a terminal alkynyl quaternary ammonium salt; this was followed by the deprotection of C2NH2 with acid to furnish the C6 quaternary ammonium CTS derivative. The structures and properties of synthesized products in the reactions were characterized by Fourier transform infrared spectroscopy, NMR, X‐ray diffraction, and thermogravimetric analysis, respectively. The effects of the reaction conditions on the degree of Schiff‐base CTS quaternization were evaluated by elemental analysis. The largest inhibition zone test and the minimum inhibitory concentration test showed that compared with CTS, the prepared CTS derivative had significantly improved antibacterial activity toward Staphylococcus aureus and Escherichia coli. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. 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Appl. Polym. Sci</addtitle><description>In this study, we explored a new method for preparing C6 quaternary ammonium chitosan (CTS) derivatives. The C2NH2 of CTS was first protected by benzaldehyde. The C6OH of CTS was then transformed into a sulfonyl ester, which was then reacted with NaN3 through nucleophilic substitution to introduce the N3 group at the CTS C6 position. This intermediate was reacted in a click chemistry reaction with a terminal alkynyl quaternary ammonium salt; this was followed by the deprotection of C2NH2 with acid to furnish the C6 quaternary ammonium CTS derivative. The structures and properties of synthesized products in the reactions were characterized by Fourier transform infrared spectroscopy, NMR, X‐ray diffraction, and thermogravimetric analysis, respectively. The effects of the reaction conditions on the degree of Schiff‐base CTS quaternization were evaluated by elemental analysis. The largest inhibition zone test and the minimum inhibitory concentration test showed that compared with CTS, the prepared CTS derivative had significantly improved antibacterial activity toward Staphylococcus aureus and Escherichia coli. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013</description><subject>Applied sciences</subject><subject>Exact sciences and technology</subject><subject>functionalization of polymers</subject><subject>Materials science</subject><subject>modification</subject><subject>Natural polymers</subject><subject>Physicochemistry of polymers</subject><subject>Polymers</subject><subject>polysaccharides</subject><subject>Starch and polysaccharides</subject><issn>0021-8995</issn><issn>1097-4628</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNo9kEtLAzEUhYMoWB8L_0FAXI4mk9dkKUVboWgRRXfhTszY6LxMZtT-e6OVru6B850L5yB0Qsk5JSS_gL4_ZwVndAdNKNEq4zIvdtEkeTQrtBb76CDGN0IoFUROULcMrocAg-9a3FUY8FTijxEGF1oIawxN07V-bLBd-aGL0OIXF_xn4j8dHlahG19XKbR1Y1JVhUuIDn_5YYVt7e178l3j4xDWR2ivgjq64_97iB6vrx6m82xxN7uZXi4yn2tKMys5zbmWynHGoRJJlRwoE5brnCsJgjAlqdVl9SKk1pIXlSyVyoUtmQPLDtHp5m8fuo_RxcG8dWOqVEdDmdRcEMVIos7-KYgW6ipAa300ffBNKm9yxQvCSZ64iw335Wu33vqUmN_RTRrd_I1uLpfLP5ES2SaRWrvvbQLCu5GKKWGebmeGz-n98_382SzYDxadhZQ</recordid><startdate>20130915</startdate><enddate>20130915</enddate><creator>Chen, Yu</creator><creator>Wang, Fengju</creator><creator>Yun, Dongran</creator><creator>Guo, Yanwen</creator><creator>Ye, Yanchun</creator><creator>Wang, Yanxi</creator><creator>Tan, Huimin</creator><general>Wiley Subscription Services, Inc., A Wiley Company</general><general>Wiley</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>IQODW</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20130915</creationdate><title>Preparation of a C6 quaternary ammonium chitosan derivative through a chitosan schiff base with click chemistry</title><author>Chen, Yu ; Wang, Fengju ; Yun, Dongran ; Guo, Yanwen ; Ye, Yanchun ; Wang, Yanxi ; Tan, Huimin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i2911-c64124967e434af5967b4a135c492476a503761c9bfd5699648f6b7725cb3eac3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Applied sciences</topic><topic>Exact sciences and technology</topic><topic>functionalization of polymers</topic><topic>Materials science</topic><topic>modification</topic><topic>Natural polymers</topic><topic>Physicochemistry of polymers</topic><topic>Polymers</topic><topic>polysaccharides</topic><topic>Starch and polysaccharides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Yu</creatorcontrib><creatorcontrib>Wang, Fengju</creatorcontrib><creatorcontrib>Yun, Dongran</creatorcontrib><creatorcontrib>Guo, Yanwen</creatorcontrib><creatorcontrib>Ye, Yanchun</creatorcontrib><creatorcontrib>Wang, Yanxi</creatorcontrib><creatorcontrib>Tan, Huimin</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Journal of applied polymer science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Yu</au><au>Wang, Fengju</au><au>Yun, Dongran</au><au>Guo, Yanwen</au><au>Ye, Yanchun</au><au>Wang, Yanxi</au><au>Tan, Huimin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Preparation of a C6 quaternary ammonium chitosan derivative through a chitosan schiff base with click chemistry</atitle><jtitle>Journal of applied polymer science</jtitle><addtitle>J. Appl. Polym. Sci</addtitle><date>2013-09-15</date><risdate>2013</risdate><volume>129</volume><issue>6</issue><spage>3185</spage><epage>3191</epage><pages>3185-3191</pages><issn>0021-8995</issn><eissn>1097-4628</eissn><coden>JAPNAB</coden><abstract>In this study, we explored a new method for preparing C6 quaternary ammonium chitosan (CTS) derivatives. The C2NH2 of CTS was first protected by benzaldehyde. The C6OH of CTS was then transformed into a sulfonyl ester, which was then reacted with NaN3 through nucleophilic substitution to introduce the N3 group at the CTS C6 position. This intermediate was reacted in a click chemistry reaction with a terminal alkynyl quaternary ammonium salt; this was followed by the deprotection of C2NH2 with acid to furnish the C6 quaternary ammonium CTS derivative. The structures and properties of synthesized products in the reactions were characterized by Fourier transform infrared spectroscopy, NMR, X‐ray diffraction, and thermogravimetric analysis, respectively. The effects of the reaction conditions on the degree of Schiff‐base CTS quaternization were evaluated by elemental analysis. The largest inhibition zone test and the minimum inhibitory concentration test showed that compared with CTS, the prepared CTS derivative had significantly improved antibacterial activity toward Staphylococcus aureus and Escherichia coli. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013</abstract><cop>Hoboken</cop><pub>Wiley Subscription Services, Inc., A Wiley Company</pub><doi>10.1002/app.38431</doi><tpages>7</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Applied sciences Exact sciences and technology functionalization of polymers Materials science modification Natural polymers Physicochemistry of polymers Polymers polysaccharides Starch and polysaccharides |
| title | Preparation of a C6 quaternary ammonium chitosan derivative through a chitosan schiff base with click chemistry |
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