N-carbamoyl amino acid solid-gas nitrosation by NO/NOx: A new route to oligopeptides via alpha-amino acid N-carboxyanhydride. Prebiotic implications
Alpha-N-Carbamoyl amino acid (CAA), whose conditions of formation in a prebiotic hydrosphere have been described previously (Taillades et al. 1998), could have been an important intermediate in prebiotic peptide synthesis through reaction with atmospheric NOx. Nitrosation of solid CAA (glycine or va...
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| Veröffentlicht in: | Journal of molecular evolution 1999-06, Vol.48 (6), p.638-645 |
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| container_title | Journal of molecular evolution |
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| creator | Taillades, J Collet, H Garrel, L Beuzelin, I Boiteau, L Choukroun, H Commeyras, A |
| description | Alpha-N-Carbamoyl amino acid (CAA), whose conditions of formation in a prebiotic hydrosphere have been described previously (Taillades et al. 1998), could have been an important intermediate in prebiotic peptide synthesis through reaction with atmospheric NOx. Nitrosation of solid CAA (glycine or valine derivative) by a 4/1 NO/O2 gaseous mixture (1 atm) yields N-carboxyanhydride (NCA) quantitatively in less than 1 h at room temperature. The crude solid NCA undergoes quantitative oligomerization (from trimer to nonamer under the conditions we used) when treated with a (bi)carbonate aqueous buffer at pH 9. We therefore suggest that part of the prebiotic amino acid activation/polymerization process may have taken place in a dry phase ("drying-lagoon" scenario). |
| doi_str_mv | 10.1007/PL00006507 |
| format | Article |
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We therefore suggest that part of the prebiotic amino acid activation/polymerization process may have taken place in a dry phase ("drying-lagoon" scenario).</description><identifier>ISSN: 0022-2844</identifier><identifier>DOI: 10.1007/PL00006507</identifier><identifier>PMID: 10229567</identifier><language>eng</language><publisher>Germany</publisher><subject>a-amino acids ; Amino Acids - chemistry ; Glycine - chemistry ; Hydrogen-Ion Concentration ; N-carboxyanhydride ; nitric oxide ; Nitric Oxide - chemistry ; Nitrosation ; oligopeptides ; Oligopeptides - chemical synthesis ; Oligopeptides - chemistry ; Oxygen - chemistry ; Peptide Biosynthesis ; prebiosis ; Space life sciences ; Valine - chemistry</subject><ispartof>Journal of molecular evolution, 1999-06, Vol.48 (6), p.638-645</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10229567$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Taillades, J</creatorcontrib><creatorcontrib>Collet, H</creatorcontrib><creatorcontrib>Garrel, L</creatorcontrib><creatorcontrib>Beuzelin, I</creatorcontrib><creatorcontrib>Boiteau, L</creatorcontrib><creatorcontrib>Choukroun, H</creatorcontrib><creatorcontrib>Commeyras, A</creatorcontrib><title>N-carbamoyl amino acid solid-gas nitrosation by NO/NOx: A new route to oligopeptides via alpha-amino acid N-carboxyanhydride. 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We therefore suggest that part of the prebiotic amino acid activation/polymerization process may have taken place in a dry phase ("drying-lagoon" scenario).</description><subject>a-amino acids</subject><subject>Amino Acids - chemistry</subject><subject>Glycine - chemistry</subject><subject>Hydrogen-Ion Concentration</subject><subject>N-carboxyanhydride</subject><subject>nitric oxide</subject><subject>Nitric Oxide - chemistry</subject><subject>Nitrosation</subject><subject>oligopeptides</subject><subject>Oligopeptides - chemical synthesis</subject><subject>Oligopeptides - chemistry</subject><subject>Oxygen - chemistry</subject><subject>Peptide Biosynthesis</subject><subject>prebiosis</subject><subject>Space life sciences</subject><subject>Valine - chemistry</subject><issn>0022-2844</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkL1OwzAUhT2AaCksPADyxJbWTuw4Zqsq_qSq7QBz5NhOa5TEwXageQ8emECLxMZd7nA-fUc6AFxhNMUIsdlmiYZLKWInYIxQHEdxRsgInHv_ihBmlCdnYISHgNOUjcHnKpLCFaK2fQVFbRoLhTQKelsZFW2Fh40JznoRjG1g0cPVerZa72_hHDb6AzrbBQ2DhQO-ta1ug1Haw3cjoKjanYj-KA9Ndt-LZtcrN4BTuHG6MDYYCU3dVkb-1PgLcFqKyuvL45-Al_u758VjtFw_PC3my6jFDIUo0ZKrmBOMMJe0zGTJBKecZhwxwrBK05hxUqKYComHjJSKK00FzVSBFcbJBNwcvK2zb532Ia-Nl7qqRKNt5_OUs4RQyv4Fh10Jidm38foIdkWtVd46UwvX57-DJ1_i3IEA</recordid><startdate>199906</startdate><enddate>199906</enddate><creator>Taillades, J</creator><creator>Collet, H</creator><creator>Garrel, L</creator><creator>Beuzelin, I</creator><creator>Boiteau, L</creator><creator>Choukroun, H</creator><creator>Commeyras, A</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>RC3</scope><scope>7X8</scope></search><sort><creationdate>199906</creationdate><title>N-carbamoyl amino acid solid-gas nitrosation by NO/NOx: A new route to oligopeptides via alpha-amino acid N-carboxyanhydride. 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Prebiotic implications</atitle><jtitle>Journal of molecular evolution</jtitle><addtitle>J Mol Evol</addtitle><date>1999-06</date><risdate>1999</risdate><volume>48</volume><issue>6</issue><spage>638</spage><epage>645</epage><pages>638-645</pages><issn>0022-2844</issn><abstract>Alpha-N-Carbamoyl amino acid (CAA), whose conditions of formation in a prebiotic hydrosphere have been described previously (Taillades et al. 1998), could have been an important intermediate in prebiotic peptide synthesis through reaction with atmospheric NOx. Nitrosation of solid CAA (glycine or valine derivative) by a 4/1 NO/O2 gaseous mixture (1 atm) yields N-carboxyanhydride (NCA) quantitatively in less than 1 h at room temperature. The crude solid NCA undergoes quantitative oligomerization (from trimer to nonamer under the conditions we used) when treated with a (bi)carbonate aqueous buffer at pH 9. We therefore suggest that part of the prebiotic amino acid activation/polymerization process may have taken place in a dry phase ("drying-lagoon" scenario).</abstract><cop>Germany</cop><pmid>10229567</pmid><doi>10.1007/PL00006507</doi><tpages>8</tpages></addata></record> |
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| ispartof | Journal of molecular evolution, 1999-06, Vol.48 (6), p.638-645 |
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| subjects | a-amino acids Amino Acids - chemistry Glycine - chemistry Hydrogen-Ion Concentration N-carboxyanhydride nitric oxide Nitric Oxide - chemistry Nitrosation oligopeptides Oligopeptides - chemical synthesis Oligopeptides - chemistry Oxygen - chemistry Peptide Biosynthesis prebiosis Space life sciences Valine - chemistry |
| title | N-carbamoyl amino acid solid-gas nitrosation by NO/NOx: A new route to oligopeptides via alpha-amino acid N-carboxyanhydride. Prebiotic implications |
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