Selective monophosphorylation of chitosan via phosphorus oxychlorideElectronic supplementary information (ESI) available. See DOI: 10.1039/c7py00123a
Chitosan was selectively monophosphorylated via reaction with phosphorus oxychloride (POCl 3 ) to enhance water solubility while avoiding polyphosphate formation. The use of POCl 3 resulted in negligible product degradation ( i.e. , breakdown of O -glycosidic bonds) even after a 3 d reaction period...
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| creator | Suchyta, Dakota J Soto, Robert J Schoenfisch, Mark H |
| description | Chitosan was selectively monophosphorylated
via
reaction with phosphorus oxychloride (POCl
3
) to enhance water solubility while avoiding polyphosphate formation. The use of POCl
3
resulted in negligible product degradation (
i.e.
, breakdown of
O
-glycosidic bonds) even after a 3 d reaction period ( |
| doi_str_mv | 10.1039/c7py00123a |
| format | Article |
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via
reaction with phosphorus oxychloride (POCl
3
) to enhance water solubility while avoiding polyphosphate formation. The use of POCl
3
resulted in negligible product degradation (
i.e.
, breakdown of
O
-glycosidic bonds) even after a 3 d reaction period (<5% weight loss). X-ray photoelectron spectroscopy (XPS) characterization of the POCl
3
-phosphorylated chitosan (P-chitosan) revealed a phosphorus to nitrogen (P/N) atomic ratio of 0.30. Phosphorus-31 nuclear magnetic resonance (
31
P NMR) spectroscopy verified the monophosphorylation of chitosan's primary and secondary alcohols, and primary amines. The calcium chelation efficiency for the phosphorylated product approached 0.05 mg Ca
2+
per mg of P-chitosan as measured by inductively coupled plasma-optical emission spectrometry (ICP-OES), indicating improved chelation over native chitosan. This selective monophosphorylation approach proved useful for modifying other biopolymers, including cellulose and alginate.
Chitosan was selectively monophosphorylated
via
reaction with phosphorus oxychloride (POCl
3
) to enhance water solubility while avoiding polyphosphate formation.</description><identifier>ISSN: 1759-9954</identifier><identifier>EISSN: 1759-9962</identifier><identifier>DOI: 10.1039/c7py00123a</identifier><language>eng</language><creationdate>2017-04</creationdate><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Suchyta, Dakota J</creatorcontrib><creatorcontrib>Soto, Robert J</creatorcontrib><creatorcontrib>Schoenfisch, Mark H</creatorcontrib><title>Selective monophosphorylation of chitosan via phosphorus oxychlorideElectronic supplementary information (ESI) available. See DOI: 10.1039/c7py00123a</title><description>Chitosan was selectively monophosphorylated
via
reaction with phosphorus oxychloride (POCl
3
) to enhance water solubility while avoiding polyphosphate formation. The use of POCl
3
resulted in negligible product degradation (
i.e.
, breakdown of
O
-glycosidic bonds) even after a 3 d reaction period (<5% weight loss). X-ray photoelectron spectroscopy (XPS) characterization of the POCl
3
-phosphorylated chitosan (P-chitosan) revealed a phosphorus to nitrogen (P/N) atomic ratio of 0.30. Phosphorus-31 nuclear magnetic resonance (
31
P NMR) spectroscopy verified the monophosphorylation of chitosan's primary and secondary alcohols, and primary amines. The calcium chelation efficiency for the phosphorylated product approached 0.05 mg Ca
2+
per mg of P-chitosan as measured by inductively coupled plasma-optical emission spectrometry (ICP-OES), indicating improved chelation over native chitosan. This selective monophosphorylation approach proved useful for modifying other biopolymers, including cellulose and alginate.
Chitosan was selectively monophosphorylated
via
reaction with phosphorus oxychloride (POCl
3
) to enhance water solubility while avoiding polyphosphate formation.</description><issn>1759-9954</issn><issn>1759-9962</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFjk1LxDAQhoMouOhevAvjTQ-7Js1-UK_axT15qPcSs1M6kmZC0i32h_h_rfh1EHRgeAeel4cR4kzJuZI6v7brMEipMm0OxEStl_ksz1fZ4fe9XByLaUrPchytFpleTcRriQ5tRz1Cy55Dw2ncODjTEXvgGmxDHSfjoScDX3yfgF8G2ziOtMPiXRHZk4W0D8Fhi74zcQDyNcf2Q3VZlNsrML0hZ54czqFEhLuH7Q38_v9UHNXGJZx-5ok43xSPt_ezmGwVIrWjvPqp6__5xV-8CrtavwE5qWVc</recordid><startdate>20170418</startdate><enddate>20170418</enddate><creator>Suchyta, Dakota J</creator><creator>Soto, Robert J</creator><creator>Schoenfisch, Mark H</creator><scope/></search><sort><creationdate>20170418</creationdate><title>Selective monophosphorylation of chitosan via phosphorus oxychlorideElectronic supplementary information (ESI) available. See DOI: 10.1039/c7py00123a</title><author>Suchyta, Dakota J ; Soto, Robert J ; Schoenfisch, Mark H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_c7py00123a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><toplevel>online_resources</toplevel><creatorcontrib>Suchyta, Dakota J</creatorcontrib><creatorcontrib>Soto, Robert J</creatorcontrib><creatorcontrib>Schoenfisch, Mark H</creatorcontrib></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Suchyta, Dakota J</au><au>Soto, Robert J</au><au>Schoenfisch, Mark H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selective monophosphorylation of chitosan via phosphorus oxychlorideElectronic supplementary information (ESI) available. See DOI: 10.1039/c7py00123a</atitle><date>2017-04-18</date><risdate>2017</risdate><volume>8</volume><issue>16</issue><spage>2552</spage><epage>2558</epage><pages>2552-2558</pages><issn>1759-9954</issn><eissn>1759-9962</eissn><abstract>Chitosan was selectively monophosphorylated
via
reaction with phosphorus oxychloride (POCl
3
) to enhance water solubility while avoiding polyphosphate formation. The use of POCl
3
resulted in negligible product degradation (
i.e.
, breakdown of
O
-glycosidic bonds) even after a 3 d reaction period (<5% weight loss). X-ray photoelectron spectroscopy (XPS) characterization of the POCl
3
-phosphorylated chitosan (P-chitosan) revealed a phosphorus to nitrogen (P/N) atomic ratio of 0.30. Phosphorus-31 nuclear magnetic resonance (
31
P NMR) spectroscopy verified the monophosphorylation of chitosan's primary and secondary alcohols, and primary amines. The calcium chelation efficiency for the phosphorylated product approached 0.05 mg Ca
2+
per mg of P-chitosan as measured by inductively coupled plasma-optical emission spectrometry (ICP-OES), indicating improved chelation over native chitosan. This selective monophosphorylation approach proved useful for modifying other biopolymers, including cellulose and alginate.
Chitosan was selectively monophosphorylated
via
reaction with phosphorus oxychloride (POCl
3
) to enhance water solubility while avoiding polyphosphate formation.</abstract><doi>10.1039/c7py00123a</doi><tpages>7</tpages></addata></record> |
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| source | Royal Society Of Chemistry Journals 2008- |
| title | Selective monophosphorylation of chitosan via phosphorus oxychlorideElectronic supplementary information (ESI) available. See DOI: 10.1039/c7py00123a |
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