High Rates and Substrate Selectivities in Water by Polyvinylimidazoles as Transaminase Enzyme Mimics with Hydrophobically Bound Pyridoxamine Derivatives as Coenzyme Mimics
Free-radical polymers of 4-vinylimidazole and copolymers with 1-dodecyl-4-vinylimidazole were used as enzyme mimics to transaminate pyruvic acid to alanine, phenylpyruvic acid to phenylalanine, and indole-3-pyruvic acid to tryptophan in water at pH 7.5 and 20 °C using pyridoxamines carrying hydropho...
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| Veröffentlicht in: | Journal of the American Chemical Society 2009-11, Vol.131 (43), p.15604-15605 |
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| container_title | Journal of the American Chemical Society |
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| creator | Skouta, Rachid Wei, Sujun Breslow, Ronald |
| description | Free-radical polymers of 4-vinylimidazole and copolymers with 1-dodecyl-4-vinylimidazole were used as enzyme mimics to transaminate pyruvic acid to alanine, phenylpyruvic acid to phenylalanine, and indole-3-pyruvic acid to tryptophan in water at pH 7.5 and 20 °C using pyridoxamines carrying hydrophobic side chains as coenzyme mimics. The best enzyme mimic accelerated the transamination of indole-3-pyruvic acid by a factor of 4 million relative to the rate without the polymer, a higher rate ratio than we had previously achieved with a polyaziridine-based enzyme mimic. The properties of various polyvinylimidazoles were compared, including those prepared with the RAFT modification of the polymerization process. |
| doi_str_mv | 10.1021/ja9072589 |
| format | Article |
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The best enzyme mimic accelerated the transamination of indole-3-pyruvic acid by a factor of 4 million relative to the rate without the polymer, a higher rate ratio than we had previously achieved with a polyaziridine-based enzyme mimic. The properties of various polyvinylimidazoles were compared, including those prepared with the RAFT modification of the polymerization process.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja9072589</identifier><identifier>PMID: 19824661</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Imidazoles - chemistry ; Molecular Mimicry ; Polyvinyls - chemistry ; Pyridoxamine - metabolism ; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization ; Spectrophotometry, Ultraviolet ; Substrate Specificity ; Transaminases - metabolism ; Water - chemistry</subject><ispartof>Journal of the American Chemical Society, 2009-11, Vol.131 (43), p.15604-15605</ispartof><rights>Copyright © 2009 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a404t-c2134cec138c487b99772ea331360c9b489c9b80bcf251f8d17e442f4906c4b73</citedby><cites>FETCH-LOGICAL-a404t-c2134cec138c487b99772ea331360c9b489c9b80bcf251f8d17e442f4906c4b73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja9072589$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja9072589$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19824661$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Skouta, Rachid</creatorcontrib><creatorcontrib>Wei, Sujun</creatorcontrib><creatorcontrib>Breslow, Ronald</creatorcontrib><title>High Rates and Substrate Selectivities in Water by Polyvinylimidazoles as Transaminase Enzyme Mimics with Hydrophobically Bound Pyridoxamine Derivatives as Coenzyme Mimics</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Free-radical polymers of 4-vinylimidazole and copolymers with 1-dodecyl-4-vinylimidazole were used as enzyme mimics to transaminate pyruvic acid to alanine, phenylpyruvic acid to phenylalanine, and indole-3-pyruvic acid to tryptophan in water at pH 7.5 and 20 °C using pyridoxamines carrying hydrophobic side chains as coenzyme mimics. The best enzyme mimic accelerated the transamination of indole-3-pyruvic acid by a factor of 4 million relative to the rate without the polymer, a higher rate ratio than we had previously achieved with a polyaziridine-based enzyme mimic. The properties of various polyvinylimidazoles were compared, including those prepared with the RAFT modification of the polymerization process.</description><subject>Imidazoles - chemistry</subject><subject>Molecular Mimicry</subject><subject>Polyvinyls - chemistry</subject><subject>Pyridoxamine - metabolism</subject><subject>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Substrate Specificity</subject><subject>Transaminases - metabolism</subject><subject>Water - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc9u1DAQxi0EokvhwAsgXxDiEPC_xPYFCZbCIhVR0SKOluM4Xa8ce7GThfSVeEm82lUpEhdbM_Ob7xvNAPAUo1cYEfx6oyXipBbyHljgmqCqxqS5DxYIIVJx0dAT8CjnTQkZEfghOMFSENY0eAF-r9z1Gn7Vo81Qhw5eTm0eUwnhpfXWjG7nRldqLsDvJZtgO8OL6OedC7N3g-v0TfT73gyvkg5ZDy7obOFZuJkHCz8XxGT4041ruJq7FLfr2DqjvZ_huzgVw4s5uS7-2vdZ-N4mt9PF9KC4jPauzGPwoNc-2yfH_xR8-3B2tVxV518-flq-Pa80Q2ysDMGUGWswFYYJ3krJObGaUkwbZGTLhCyvQK3pSY170WFuGSM9k6gxrOX0FLw56G6ndrCdsaFsxKttcoNOs4raqX8rwa3VddwpwiVDVBaBF0eBFH9MNo9qcNlY73WwccqK0zJJXQtcyJcH0qSYc7L9rQtGan9bdXvbwj67O9Zf8njMAjw_ANpktYlTCmVL_xH6A7BYr8Y</recordid><startdate>20091104</startdate><enddate>20091104</enddate><creator>Skouta, Rachid</creator><creator>Wei, Sujun</creator><creator>Breslow, Ronald</creator><general>American Chemical Society</general><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>7X8</scope><scope>5PM</scope></search><sort><creationdate>20091104</creationdate><title>High Rates and Substrate Selectivities in Water by Polyvinylimidazoles as Transaminase Enzyme Mimics with Hydrophobically Bound Pyridoxamine Derivatives as Coenzyme Mimics</title><author>Skouta, Rachid ; Wei, Sujun ; Breslow, Ronald</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a404t-c2134cec138c487b99772ea331360c9b489c9b80bcf251f8d17e442f4906c4b73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Imidazoles - chemistry</topic><topic>Molecular Mimicry</topic><topic>Polyvinyls - chemistry</topic><topic>Pyridoxamine - metabolism</topic><topic>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Substrate Specificity</topic><topic>Transaminases - metabolism</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Skouta, Rachid</creatorcontrib><creatorcontrib>Wei, Sujun</creatorcontrib><creatorcontrib>Breslow, Ronald</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Skouta, Rachid</au><au>Wei, Sujun</au><au>Breslow, Ronald</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>High Rates and Substrate Selectivities in Water by Polyvinylimidazoles as Transaminase Enzyme Mimics with Hydrophobically Bound Pyridoxamine Derivatives as Coenzyme Mimics</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2009-11-04</date><risdate>2009</risdate><volume>131</volume><issue>43</issue><spage>15604</spage><epage>15605</epage><pages>15604-15605</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>Free-radical polymers of 4-vinylimidazole and copolymers with 1-dodecyl-4-vinylimidazole were used as enzyme mimics to transaminate pyruvic acid to alanine, phenylpyruvic acid to phenylalanine, and indole-3-pyruvic acid to tryptophan in water at pH 7.5 and 20 °C using pyridoxamines carrying hydrophobic side chains as coenzyme mimics. The best enzyme mimic accelerated the transamination of indole-3-pyruvic acid by a factor of 4 million relative to the rate without the polymer, a higher rate ratio than we had previously achieved with a polyaziridine-based enzyme mimic. The properties of various polyvinylimidazoles were compared, including those prepared with the RAFT modification of the polymerization process.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>19824661</pmid><doi>10.1021/ja9072589</doi><tpages>2</tpages><oa>free_for_read</oa></addata></record> |
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| source | MEDLINE; ACS Publications |
| subjects | Imidazoles - chemistry Molecular Mimicry Polyvinyls - chemistry Pyridoxamine - metabolism Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Spectrophotometry, Ultraviolet Substrate Specificity Transaminases - metabolism Water - chemistry |
| title | High Rates and Substrate Selectivities in Water by Polyvinylimidazoles as Transaminase Enzyme Mimics with Hydrophobically Bound Pyridoxamine Derivatives as Coenzyme Mimics |
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