Optimized Diazo Scaffold for Protein Esterification
The O-alkylation of carboxylic acids with diazo compounds provides a means to esterify carboxylic acids in aqueous solution. A Hammett analysis of the reactivity of diazo compounds derived from phenylglycinamide revealed that the (p-methylphenyl)glycinamide scaffold has an especially high reaction...
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| Veröffentlicht in: | Organic letters 2015-05, Vol.17 (10), p.2358-2361 |
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| creator | Mix, Kalie A Raines, Ronald T |
| description | The O-alkylation of carboxylic acids with diazo compounds provides a means to esterify carboxylic acids in aqueous solution. A Hammett analysis of the reactivity of diazo compounds derived from phenylglycinamide revealed that the (p-methylphenyl)glycinamide scaffold has an especially high reaction rate and ester/alcohol product ratio and esterifies protein carboxyl groups more efficiently than any known reagent. |
| doi_str_mv | 10.1021/acs.orglett.5b00840 |
| format | Article |
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A Hammett analysis of the reactivity of diazo compounds derived from phenylglycinamide revealed that the (p-methylphenyl)glycinamide scaffold has an especially high reaction rate and ester/alcohol product ratio and esterifies protein carboxyl groups more efficiently than any known reagent.</description><subject>Azo Compounds - chemistry</subject><subject>Carboxylic Acids - chemistry</subject><subject>Esters - chemical synthesis</subject><subject>Esters - chemistry</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Proteins - chemical synthesis</subject><subject>Proteins - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1LAzEQhoMotlZ_gSB79NI2H7vZzUWQWj-gUEE9h2x2tqZsNzXJCvbXm9Ja9OJphpn3fWd4ELokeEQwJWOl_ci6RQMhjLIS4yLFR6hPMsqGOc7o8aHnuIfOvF9iTOJEnKIezQQrBON9xObrYFZmA1VyZ9TGJi9a1bVtqqS2Lnl2NoBpk6kP4ExttArGtufopFaNh4t9HaC3--nr5HE4mz88TW5nQ5UREobxSUELVilGNCUsr4CJugJBVc4BC5JWnApRsJJooBoySCudU6xyUueclJgN0M0ud92VK6g0tMGpRq6dWSn3Ja0y8u-mNe9yYT9lyiMAzmLA9T7A2Y8OfJAr4zU0jWrBdl4SXhDKOcuLKGU7qXbWewf14QzBcotbRtxyj1vucUfX1e8PD54fvlEw3gm27qXtXBuB_Rv5DX7JjxU</recordid><startdate>20150515</startdate><enddate>20150515</enddate><creator>Mix, Kalie A</creator><creator>Raines, Ronald T</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>20150515</creationdate><title>Optimized Diazo Scaffold for Protein Esterification</title><author>Mix, Kalie A ; Raines, Ronald T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a511t-1029283da31c2137de39fde92a76e0914d629983b1ce2ce5e4dc720a71f761b03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Azo Compounds - chemistry</topic><topic>Carboxylic Acids - chemistry</topic><topic>Esters - chemical synthesis</topic><topic>Esters - chemistry</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Proteins - chemical synthesis</topic><topic>Proteins - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mix, Kalie A</creatorcontrib><creatorcontrib>Raines, Ronald T</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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mix, Kalie A</au><au>Raines, Ronald T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Optimized Diazo Scaffold for Protein Esterification</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2015-05, Vol.17 (10), p.2358-2361 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Azo Compounds - chemistry Carboxylic Acids - chemistry Esters - chemical synthesis Esters - chemistry Models, Molecular Molecular Structure Proteins - chemical synthesis Proteins - chemistry |
| title | Optimized Diazo Scaffold for Protein Esterification |
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