A straightforward approach towards cyclic peptides via ring-closing metathesis--scope and limitations
N- and C-terminal diallylated peptides are obtained by several approaches, such as peptide Claisen rearrangement, N- and O- allylation, and the Ugi reaction of allyl-protected components. These diallylated peptides are suitable substrates for ring-closing metathesis and the success of this cyclisati...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2005-01, Vol.3 (1), p.136-145 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Kazmaier, Uli Hebach, Christina Watzke, Anja Maier, Sabine Mues, Heike Huch, Volker |
| description | N- and C-terminal diallylated peptides are obtained by several approaches, such as peptide Claisen rearrangement, N- and O- allylation, and the Ugi reaction of allyl-protected components. These diallylated peptides are suitable substrates for ring-closing metathesis and the success of this cyclisation was investigated with respect to the ring size, the position of the allyl moieties and the reaction parameters. In general, excellent yields are obtained for cyclisation of allyl glycine subunits and N-allylated amides, while allyl esters and allyl carbamates often presented serious problems. However, yields of up to 73% were obtained under optimised conditions, and the new generated double bond is formed with excellent trans-selectivity. |
| doi_str_mv | 10.1039/b411228h |
| format | Article |
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However, yields of up to 73% were obtained under optimised conditions, and the new generated double bond is formed with excellent trans-selectivity.</description><subject>Catalysis</subject><subject>Cyclization</subject><subject>Organometallic Compounds - chemistry</subject><subject>Peptides, Cyclic - chemical synthesis</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Protein Conformation</subject><subject>Ruthenium - chemistry</subject><subject>Stereoisomerism</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkFFLwzAUhYMobk7BXyB5El-qSdM2y-Mc6oSBL_pckvR2jbRNzc2U_Xs7NvTlnnsvHwfOIeSas3vOhHowGedpOm9OyJRnUiYsF-r0b0_ZhFwgfjLGlSyyczLhecHSgqkpgQXFGLTbNLH24UeHiuphCF7bhka_v5HanW2dpQMM0VWA9NtpGly_SWzrcVTaQdSxAXSYJGj9AFT3FW1d58a_8z1ekrNatwhXR52Rj-en9-UqWb-9vC4X68SKTMaE26Ku0rm0hTJ1JmRtcs6UAAYit3lqeaZUJjSrag3WwFxIq41RDIBVuTFzMSO3B98xwdcWMJadQwttq3vwWywLKdI8H-eM3B1AGzxigLocgut02JWclftKy8dDpasRvTl6bk0H1T947FD8AjA1c10</recordid><startdate>20050107</startdate><enddate>20050107</enddate><creator>Kazmaier, Uli</creator><creator>Hebach, Christina</creator><creator>Watzke, Anja</creator><creator>Maier, Sabine</creator><creator>Mues, Heike</creator><creator>Huch, Volker</creator><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></search><sort><creationdate>20050107</creationdate><title>A straightforward approach towards cyclic peptides via ring-closing metathesis--scope and limitations</title><author>Kazmaier, Uli ; Hebach, Christina ; Watzke, Anja ; Maier, Sabine ; Mues, Heike ; Huch, Volker</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c347t-1c6fd287c69bf437fb51093e0e35c52c149943a0dfaecbe837cabb90ee0d5bb83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Catalysis</topic><topic>Cyclization</topic><topic>Organometallic Compounds - chemistry</topic><topic>Peptides, Cyclic - chemical synthesis</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Protein Conformation</topic><topic>Ruthenium - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kazmaier, Uli</creatorcontrib><creatorcontrib>Hebach, Christina</creatorcontrib><creatorcontrib>Watzke, Anja</creatorcontrib><creatorcontrib>Maier, Sabine</creatorcontrib><creatorcontrib>Mues, Heike</creatorcontrib><creatorcontrib>Huch, Volker</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><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kazmaier, Uli</au><au>Hebach, Christina</au><au>Watzke, Anja</au><au>Maier, Sabine</au><au>Mues, Heike</au><au>Huch, Volker</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A straightforward approach towards cyclic peptides via ring-closing metathesis--scope and limitations</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2005-01-07</date><risdate>2005</risdate><volume>3</volume><issue>1</issue><spage>136</spage><epage>145</epage><pages>136-145</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>N- and C-terminal diallylated peptides are obtained by several approaches, such as peptide Claisen rearrangement, N- and O- allylation, and the Ugi reaction of allyl-protected components. 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| source | MEDLINE; Royal Society of Chemistry Journals Archive (1841-2007); Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Catalysis Cyclization Organometallic Compounds - chemistry Peptides, Cyclic - chemical synthesis Peptides, Cyclic - chemistry Protein Conformation Ruthenium - chemistry Stereoisomerism |
| title | A straightforward approach towards cyclic peptides via ring-closing metathesis--scope and limitations |
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