1H‑Azepine-2-oxo-5-amino-5-carboxylic Acid: A 310 Helix Inducer and an Effective Tool for Functionalized Gold Nanoparticles
A new α,α-disubstituted constrained glutamine analogue has been designed to decorate gold nanoparticles and to induce a 310-helix when inserted in peptides. Using an efficient “one-pot” asymmetric Schmidt reaction between 4-disubstituted-cyclohexanone and hydroxyalkylazides, 1H-azepine-2-oxo-5-amino...
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| Veröffentlicht in: | Journal of organic chemistry 2015-06, Vol.80 (11), p.5507-5516 |
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| container_end_page | 5516 |
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| container_issue | 11 |
| container_start_page | 5507 |
| container_title | Journal of organic chemistry |
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| creator | Pellegrino, Sara Bonetti, Andrea Clerici, Francesca Contini, Alessandro Moretto, Alessandro Soave, Raffaella Gelmi, Maria Luisa |
| description | A new α,α-disubstituted constrained glutamine analogue has been designed to decorate gold nanoparticles and to induce a 310-helix when inserted in peptides. Using an efficient “one-pot” asymmetric Schmidt reaction between 4-disubstituted-cyclohexanone and hydroxyalkylazides, 1H-azepine-2-oxo-5-amino-5-carboxylic acid was prepared. The main (R) isomer was inserted at the N-terminus in a very short peptide sequence (i.e., PhCO-(R)-Oxo-Azn-l-Ala-Aib-l-AlaNHMe) and a stable 310-helix conformation was obtained, as verified by both NMR experiments and molecular dynamics (MD) simulations. Finally, the presence of the hydroxyl chain at the nitrogen atom of the ring allowed for the preparation of covered chiral gold nanoparticles. |
| doi_str_mv | 10.1021/acs.joc.5b00396 |
| format | Article |
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Using an efficient “one-pot” asymmetric Schmidt reaction between 4-disubstituted-cyclohexanone and hydroxyalkylazides, 1H-azepine-2-oxo-5-amino-5-carboxylic acid was prepared. The main (R) isomer was inserted at the N-terminus in a very short peptide sequence (i.e., PhCO-(R)-Oxo-Azn-l-Ala-Aib-l-AlaNHMe) and a stable 310-helix conformation was obtained, as verified by both NMR experiments and molecular dynamics (MD) simulations. 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Org. Chem</addtitle><description>A new α,α-disubstituted constrained glutamine analogue has been designed to decorate gold nanoparticles and to induce a 310-helix when inserted in peptides. Using an efficient “one-pot” asymmetric Schmidt reaction between 4-disubstituted-cyclohexanone and hydroxyalkylazides, 1H-azepine-2-oxo-5-amino-5-carboxylic acid was prepared. The main (R) isomer was inserted at the N-terminus in a very short peptide sequence (i.e., PhCO-(R)-Oxo-Azn-l-Ala-Aib-l-AlaNHMe) and a stable 310-helix conformation was obtained, as verified by both NMR experiments and molecular dynamics (MD) simulations. Finally, the presence of the hydroxyl chain at the nitrogen atom of the ring allowed for the preparation of covered chiral gold nanoparticles.</description><subject>Amino Acid Sequence</subject><subject>Azepines - chemical synthesis</subject><subject>Azepines - chemistry</subject><subject>Carboxylic Acids - chemical synthesis</subject><subject>Carboxylic Acids - chemistry</subject><subject>Gold - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Models, Molecular</subject><subject>Nanoparticles - chemistry</subject><subject>Peptides - chemistry</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo1kU9LAzEQxYMotv45e5McBUlNJpt011uR2hZEL3peZpMUUtJN3e1KKwh-Bb-in8SU1oFh4PHjwbxHyJXgA8FB3KFpB4toBqriXBb6iPSFAs50wbNj0uccgEnQskfO2nbB0yilTkkPVCHzXEGffInp7_fP6NOtfO0YsLiJTDFc-np3DTZV3GyDN3RkvL2nIyoFp1MX_IbOatsZ11CsbVo6ns-dWfsPR19jDHQeG_rY1UmJNQb_6SydxGDpM9Zxhc3am-DaC3Iyx9C6y8M9J2-P49eHKXt6mcweRk8MhZSaCZB5VdjKZMMKUEo7NLrIEKTiZohCmwIEoDN6mCel4jIDgYXQzjrMlZLynNzsfVdNfO9cuy6XvjUuBKxd7NpS6FxnADlkCb0-oF21dLZcNX6Jzbb8jywBt3sgZV8uYtek95IDL3eFlHvRlIdC5B_K6Huu</recordid><startdate>20150605</startdate><enddate>20150605</enddate><creator>Pellegrino, Sara</creator><creator>Bonetti, Andrea</creator><creator>Clerici, Francesca</creator><creator>Contini, Alessandro</creator><creator>Moretto, Alessandro</creator><creator>Soave, Raffaella</creator><creator>Gelmi, Maria Luisa</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>7X8</scope></search><sort><creationdate>20150605</creationdate><title>1H‑Azepine-2-oxo-5-amino-5-carboxylic Acid: A 310 Helix Inducer and an Effective Tool for Functionalized Gold Nanoparticles</title><author>Pellegrino, Sara ; Bonetti, Andrea ; Clerici, Francesca ; Contini, Alessandro ; Moretto, Alessandro ; Soave, Raffaella ; Gelmi, Maria Luisa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a1336-1238b9dbc47b2a33d7c694a2350c7a16c9212aec67850cb03421a916edea85533</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Amino Acid Sequence</topic><topic>Azepines - chemical synthesis</topic><topic>Azepines - chemistry</topic><topic>Carboxylic Acids - chemical synthesis</topic><topic>Carboxylic Acids - chemistry</topic><topic>Gold - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Models, Molecular</topic><topic>Nanoparticles - chemistry</topic><topic>Peptides - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pellegrino, Sara</creatorcontrib><creatorcontrib>Bonetti, Andrea</creatorcontrib><creatorcontrib>Clerici, Francesca</creatorcontrib><creatorcontrib>Contini, Alessandro</creatorcontrib><creatorcontrib>Moretto, Alessandro</creatorcontrib><creatorcontrib>Soave, Raffaella</creatorcontrib><creatorcontrib>Gelmi, Maria Luisa</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pellegrino, Sara</au><au>Bonetti, Andrea</au><au>Clerici, Francesca</au><au>Contini, Alessandro</au><au>Moretto, Alessandro</au><au>Soave, Raffaella</au><au>Gelmi, Maria Luisa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>1H‑Azepine-2-oxo-5-amino-5-carboxylic Acid: A 310 Helix Inducer and an Effective Tool for Functionalized Gold Nanoparticles</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2015-06-05</date><risdate>2015</risdate><volume>80</volume><issue>11</issue><spage>5507</spage><epage>5516</epage><pages>5507-5516</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A new α,α-disubstituted constrained glutamine analogue has been designed to decorate gold nanoparticles and to induce a 310-helix when inserted in peptides. Using an efficient “one-pot” asymmetric Schmidt reaction between 4-disubstituted-cyclohexanone and hydroxyalkylazides, 1H-azepine-2-oxo-5-amino-5-carboxylic acid was prepared. The main (R) isomer was inserted at the N-terminus in a very short peptide sequence (i.e., PhCO-(R)-Oxo-Azn-l-Ala-Aib-l-AlaNHMe) and a stable 310-helix conformation was obtained, as verified by both NMR experiments and molecular dynamics (MD) simulations. Finally, the presence of the hydroxyl chain at the nitrogen atom of the ring allowed for the preparation of covered chiral gold nanoparticles.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25938852</pmid><doi>10.1021/acs.joc.5b00396</doi><tpages>10</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Journal of organic chemistry, 2015-06, Vol.80 (11), p.5507-5516 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Amino Acid Sequence Azepines - chemical synthesis Azepines - chemistry Carboxylic Acids - chemical synthesis Carboxylic Acids - chemistry Gold - chemistry Magnetic Resonance Spectroscopy Models, Molecular Nanoparticles - chemistry Peptides - chemistry Stereoisomerism |
| title | 1H‑Azepine-2-oxo-5-amino-5-carboxylic Acid: A 310 Helix Inducer and an Effective Tool for Functionalized Gold Nanoparticles |
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