Characterization of Acyl Adenyl Anhydrides: Differences in the Hydrolytic Rates of Fatty Acyl-AMP and Aminoacyl-AMP Derivatives
An improved procedure has been developed to prepare RCOOPO2-Ado (R = C6H13 and C15H31), the intermediate in the enzymatic synthesis of acyl-CoA's. The product has been characterized by spectral methods which, in turn, were used to define the hydrolysis rates of RCO-AMP. When R is a fatty acyl g...
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Veröffentlicht in: | Journal of organic chemistry 1998-11, Vol.63 (24), p.8661-8667 |
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container_title | Journal of organic chemistry |
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creator | Schall, Otto F Suzuki, Iwao Murray, Clare L Gordon, Jeffrey I Gokel, George W |
description | An improved procedure has been developed to prepare RCOOPO2-Ado (R = C6H13 and C15H31), the intermediate in the enzymatic synthesis of acyl-CoA's. The product has been characterized by spectral methods which, in turn, were used to define the hydrolysis rates of RCO-AMP. When R is a fatty acyl group, the hydrolysis rate is 10-fold slower than when R is aminoacyl. In both cases, the hydrolysis rate is enhanced by Mg2+. We speculate that the rate acceleration is due to intramolecular participation of the second carbonyl group in the aminoacyl residue. |
doi_str_mv | 10.1021/jo971874f |
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The product has been characterized by spectral methods which, in turn, were used to define the hydrolysis rates of RCO-AMP. When R is a fatty acyl group, the hydrolysis rate is 10-fold slower than when R is aminoacyl. In both cases, the hydrolysis rate is enhanced by Mg2+. We speculate that the rate acceleration is due to intramolecular participation of the second carbonyl group in the aminoacyl residue.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo971874f</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Journal of organic chemistry, 1998-11, Vol.63 (24), p.8661-8667</ispartof><rights>Copyright © 1998 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a295t-df498c234a8caa9f6f980b7314c74350ec7634470c683136c06028444fd29ca3</citedby><cites>FETCH-LOGICAL-a295t-df498c234a8caa9f6f980b7314c74350ec7634470c683136c06028444fd29ca3</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/jo971874f$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo971874f$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids></links><search><creatorcontrib>Schall, Otto F</creatorcontrib><creatorcontrib>Suzuki, Iwao</creatorcontrib><creatorcontrib>Murray, Clare L</creatorcontrib><creatorcontrib>Gordon, Jeffrey I</creatorcontrib><creatorcontrib>Gokel, George W</creatorcontrib><title>Characterization of Acyl Adenyl Anhydrides: Differences in the Hydrolytic Rates of Fatty Acyl-AMP and Aminoacyl-AMP Derivatives</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>An improved procedure has been developed to prepare RCOOPO2-Ado (R = C6H13 and C15H31), the intermediate in the enzymatic synthesis of acyl-CoA's. The product has been characterized by spectral methods which, in turn, were used to define the hydrolysis rates of RCO-AMP. When R is a fatty acyl group, the hydrolysis rate is 10-fold slower than when R is aminoacyl. In both cases, the hydrolysis rate is enhanced by Mg2+. We speculate that the rate acceleration is due to intramolecular participation of the second carbonyl group in the aminoacyl residue.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><recordid>eNptkLtOAzEQRS0EEiFQ8AduKCgW_NwH3ZIQghRERFLRrIzXVhwSL7JNxFIhOn6TL8EhkIpprjRzdEYzABxjdIYRwefzpshwnjG9AzqYE5SkBWK7oIMQIQklKd0HB97PUSzOeQd89GbCCRmUM28imMbCRsNStgtY1squw87a2pla-Yuv90_YN1orp6xUHhoLw0zBYZw3izYYCe9FiP1oGIgQ2h9PUt6OobA1LJfGNuKv048LV3HhSvlDsKfFwquj3-yC6eBq2hsmo7vrm145SgQpeEhqzYpcEspELoUodKqLHD1mFDOZMcqRkllKGcuQTHOKaSpRikjOGNM1KaSgXXC60UrXeO-Urp6dWQrXVhhV699V299FNtmwxgf1ugWFe6rSjGa8mo4nFb3sP_BJb1xdRv5kwwvpo-bF2XjIP95v_bx9zQ</recordid><startdate>19981127</startdate><enddate>19981127</enddate><creator>Schall, Otto F</creator><creator>Suzuki, Iwao</creator><creator>Murray, Clare L</creator><creator>Gordon, Jeffrey I</creator><creator>Gokel, George W</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19981127</creationdate><title>Characterization of Acyl Adenyl Anhydrides: Differences in the Hydrolytic Rates of Fatty Acyl-AMP and Aminoacyl-AMP Derivatives</title><author>Schall, Otto F ; Suzuki, Iwao ; Murray, Clare L ; Gordon, Jeffrey I ; Gokel, George W</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a295t-df498c234a8caa9f6f980b7314c74350ec7634470c683136c06028444fd29ca3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Schall, Otto F</creatorcontrib><creatorcontrib>Suzuki, Iwao</creatorcontrib><creatorcontrib>Murray, Clare L</creatorcontrib><creatorcontrib>Gordon, Jeffrey I</creatorcontrib><creatorcontrib>Gokel, George W</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Schall, Otto F</au><au>Suzuki, Iwao</au><au>Murray, Clare L</au><au>Gordon, Jeffrey I</au><au>Gokel, George W</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Characterization of Acyl Adenyl Anhydrides: Differences in the Hydrolytic Rates of Fatty Acyl-AMP and Aminoacyl-AMP Derivatives</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>1998-11-27</date><risdate>1998</risdate><volume>63</volume><issue>24</issue><spage>8661</spage><epage>8667</epage><pages>8661-8667</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>An improved procedure has been developed to prepare RCOOPO2-Ado (R = C6H13 and C15H31), the intermediate in the enzymatic synthesis of acyl-CoA's. The product has been characterized by spectral methods which, in turn, were used to define the hydrolysis rates of RCO-AMP. When R is a fatty acyl group, the hydrolysis rate is 10-fold slower than when R is aminoacyl. In both cases, the hydrolysis rate is enhanced by Mg2+. We speculate that the rate acceleration is due to intramolecular participation of the second carbonyl group in the aminoacyl residue.</abstract><pub>American Chemical Society</pub><doi>10.1021/jo971874f</doi><tpages>7</tpages></addata></record> |
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title | Characterization of Acyl Adenyl Anhydrides: Differences in the Hydrolytic Rates of Fatty Acyl-AMP and Aminoacyl-AMP Derivatives |
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