C-Terminal lactamization of peptides
Solid-phase synthesis of peptides (SPPS) with release through formation of C-terminal γ-, δ-, or -lactams is presented. The natural products ciliatamide A and C were synthesized in up to 90% yield. Peptides carrying C-terminal lactams were shown to possess increased bio-stability and comparable biol...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2021-01, Vol.57 (7), p.895-898 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Fischer, Niklas H Nielsen, Daniel S Palmer, Daniel Meldal, Morten Diness, Frederik |
| description | Solid-phase synthesis of peptides (SPPS) with release through formation of C-terminal γ-, δ-, or -lactams is presented. The natural products ciliatamide A and C were synthesized in up to 90% yield. Peptides carrying C-terminal lactams were shown to possess increased bio-stability and comparable biological activity as compared to the parent non-lactamized peptide amides.
New solid-phase based methods have allowed efficient synthesis of natural products and novel peptide hormone derivatives with a C-terminal lactam. |
| doi_str_mv | 10.1039/d0cc06018f |
| format | Article |
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New solid-phase based methods have allowed efficient synthesis of natural products and novel peptide hormone derivatives with a C-terminal lactam.</description><subject>Amides</subject><subject>Biological activity</subject><subject>Natural products</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Peptides</subject><subject>Solid phase synthesis</subject><subject>Solid phases</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpd0EFLwzAUB_AgipvTi3dloAcRqklfkzZHqU6FgZcJ3kqSvkBHu9akPcxPb-bmBHN5gffj8d6fkHNG7xgFeV9SY6igLLMHZMxAJBFPso_DzZ_LKIWEj8iJ90saHuPZMRkBgEiBijG5zqMFuqZaqXpaK9OrpvpSfdWupq2ddtj1VYn-lBxZVXs829UJeZ89LfKXaP72_Jo_zCMDkPYRB50CK40xiMgYZzrWoC0IY8MiRnJrrZRaoU4zLKnOAqIxR6AMhaAJTMjNdm7n2s8BfV80lTdY12qF7eCLOAnHMC6pDPTqH122gwtXbFTGRBxLmQV1u1XGtd47tEXnqka5dcFoscmueKR5_pPdLODL3chBN1ju6W9YAVxsgfNm3_0LH74BUYZxQg</recordid><startdate>20210128</startdate><enddate>20210128</enddate><creator>Fischer, Niklas H</creator><creator>Nielsen, Daniel S</creator><creator>Palmer, Daniel</creator><creator>Meldal, Morten</creator><creator>Diness, Frederik</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-5098-7198</orcidid></search><sort><creationdate>20210128</creationdate><title>C-Terminal lactamization of peptides</title><author>Fischer, Niklas H ; Nielsen, Daniel S ; Palmer, Daniel ; Meldal, Morten ; Diness, Frederik</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-53b731dccceee1151b2b3bf36cf359c95fff99baeb78ed0b8e11025e301e66043</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Amides</topic><topic>Biological activity</topic><topic>Natural products</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Peptides</topic><topic>Solid phase synthesis</topic><topic>Solid phases</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fischer, Niklas H</creatorcontrib><creatorcontrib>Nielsen, Daniel S</creatorcontrib><creatorcontrib>Palmer, Daniel</creatorcontrib><creatorcontrib>Meldal, Morten</creatorcontrib><creatorcontrib>Diness, Frederik</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fischer, Niklas H</au><au>Nielsen, Daniel S</au><au>Palmer, Daniel</au><au>Meldal, Morten</au><au>Diness, Frederik</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>C-Terminal lactamization of peptides</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2021-01-28</date><risdate>2021</risdate><volume>57</volume><issue>7</issue><spage>895</spage><epage>898</epage><pages>895-898</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>Solid-phase synthesis of peptides (SPPS) with release through formation of C-terminal γ-, δ-, or -lactams is presented. The natural products ciliatamide A and C were synthesized in up to 90% yield. Peptides carrying C-terminal lactams were shown to possess increased bio-stability and comparable biological activity as compared to the parent non-lactamized peptide amides.
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| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2021-01, Vol.57 (7), p.895-898 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_crossref_primary_10_1039_D0CC06018F |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Amides Biological activity Natural products NMR Nuclear magnetic resonance Peptides Solid phase synthesis Solid phases |
| title | C-Terminal lactamization of peptides |
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