Microwave-assisted solid-phase synthesis of side-chain to side-chain lactam-bridge cyclic peptides
[Display omitted] Side-chain to side-chain lactam-bridged cyclic peptides have been utilized as therapeutic agents and biochemical tools. Previous synthetic methods of these peptides need special reaction conditions, form side products and take longer reaction times. Herein, an efficient microwave-a...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2015-12, Vol.25 (24), p.5708-5711 |
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| container_issue | 24 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Tala, Srinivasa R. Schnell, Sathya M. Haskell-Luevano, Carrie |
| description | [Display omitted]
Side-chain to side-chain lactam-bridged cyclic peptides have been utilized as therapeutic agents and biochemical tools. Previous synthetic methods of these peptides need special reaction conditions, form side products and take longer reaction times. Herein, an efficient microwave-assisted synthesis of side-chain to side-chain lactam-bridge cyclic peptides SHU9119 and MTII is reported. The synthesis time and efforts are significantly reduced in the present method, without side product formation. The analytical and pharmacological data of the synthesized cyclic peptides are in accordance with the commercially obtained compounds. This new method could be used to synthesize other side-chain to side-chain lactam-bridge peptides and amenable to automation and extensive SAR compound derivatization. |
| doi_str_mv | 10.1016/j.bmcl.2015.10.095 |
| format | Article |
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Side-chain to side-chain lactam-bridged cyclic peptides have been utilized as therapeutic agents and biochemical tools. Previous synthetic methods of these peptides need special reaction conditions, form side products and take longer reaction times. Herein, an efficient microwave-assisted synthesis of side-chain to side-chain lactam-bridge cyclic peptides SHU9119 and MTII is reported. The synthesis time and efforts are significantly reduced in the present method, without side product formation. The analytical and pharmacological data of the synthesized cyclic peptides are in accordance with the commercially obtained compounds. This new method could be used to synthesize other side-chain to side-chain lactam-bridge peptides and amenable to automation and extensive SAR compound derivatization.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2015.10.095</identifier><identifier>PMID: 26555357</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>alpha-MSH - analogs & derivatives ; alpha-MSH - chemical synthesis ; alpha-MSH - chemistry ; alpha-MSH - metabolism ; Animals ; Cyclic peptides ; Lactam-bridge cyclic peptides ; Lactams - chemistry ; Melanocyte-Stimulating Hormones - chemical synthesis ; Melanocyte-Stimulating Hormones - chemistry ; Melanocyte-Stimulating Hormones - metabolism ; Mice ; Microwave assisted synthesis ; Microwaves ; MTII ; Peptides, Cyclic - chemical synthesis ; Peptides, Cyclic - chemistry ; Protein Binding ; Receptors, Melanocortin - antagonists & inhibitors ; Receptors, Melanocortin - metabolism ; SHU9119 ; Solid-Phase Synthesis Techniques</subject><ispartof>Bioorganic & medicinal chemistry letters, 2015-12, Vol.25 (24), p.5708-5711</ispartof><rights>2015 Elsevier Ltd</rights><rights>Copyright © 2015 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c455t-a9e291502ec2da905b4d224b6c627629f560ae18ec0f0f2793ad7af815cc76823</citedby><cites>FETCH-LOGICAL-c455t-a9e291502ec2da905b4d224b6c627629f560ae18ec0f0f2793ad7af815cc76823</cites><orcidid>0000-0002-6783-5972</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2015.10.095$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26555357$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tala, Srinivasa R.</creatorcontrib><creatorcontrib>Schnell, Sathya M.</creatorcontrib><creatorcontrib>Haskell-Luevano, Carrie</creatorcontrib><title>Microwave-assisted solid-phase synthesis of side-chain to side-chain lactam-bridge cyclic peptides</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
Side-chain to side-chain lactam-bridged cyclic peptides have been utilized as therapeutic agents and biochemical tools. Previous synthetic methods of these peptides need special reaction conditions, form side products and take longer reaction times. Herein, an efficient microwave-assisted synthesis of side-chain to side-chain lactam-bridge cyclic peptides SHU9119 and MTII is reported. The synthesis time and efforts are significantly reduced in the present method, without side product formation. The analytical and pharmacological data of the synthesized cyclic peptides are in accordance with the commercially obtained compounds. This new method could be used to synthesize other side-chain to side-chain lactam-bridge peptides and amenable to automation and extensive SAR compound derivatization.</description><subject>alpha-MSH - analogs & derivatives</subject><subject>alpha-MSH - chemical synthesis</subject><subject>alpha-MSH - chemistry</subject><subject>alpha-MSH - metabolism</subject><subject>Animals</subject><subject>Cyclic peptides</subject><subject>Lactam-bridge cyclic peptides</subject><subject>Lactams - chemistry</subject><subject>Melanocyte-Stimulating Hormones - chemical synthesis</subject><subject>Melanocyte-Stimulating Hormones - chemistry</subject><subject>Melanocyte-Stimulating Hormones - metabolism</subject><subject>Mice</subject><subject>Microwave assisted synthesis</subject><subject>Microwaves</subject><subject>MTII</subject><subject>Peptides, Cyclic - chemical synthesis</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Protein Binding</subject><subject>Receptors, Melanocortin - antagonists & inhibitors</subject><subject>Receptors, Melanocortin - metabolism</subject><subject>SHU9119</subject><subject>Solid-Phase Synthesis Techniques</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kU2LFDEQhoMo7uzqH_AgffSS2SSdpLtBBFncD1jxouAtpCvVOxm6O22SGZl_b4ZZl_XiKaTqqTehHkLecbbmjOvL7bqfYFwLxlUprFmnXpAVl1rSWjL1kqxYpxltO_nzjJyntGWMSybla3ImtFKqVs2K9F89xPDb7pHalHzK6KoURu_osrEJq3SY8wZLowpDlbxDChvr5yqH57fRQrYT7aN3D1jBAUYP1YJLLkh6Q14Ndkz49vG8ID-uv3y_uqX3327urj7fU5BKZWo7FB1XTCAIZzumeumEkL0GLRotukFpZpG3CGxgg2i62rrGDi1XAI1uRX1BPp1yl10_oQOcc7SjWaKfbDyYYL35tzP7jXkIeyO1kpK3JeDDY0AMv3aYspl8AhxHO2PYJcObWtVCN0wWVJzQsryUIg5Pz3BmjnLM1hzlmKOcY63IKUPvn3_waeSvjQJ8PAFY1rT3GE0CjzOg8xEhGxf8__L_AK8sotM</recordid><startdate>20151215</startdate><enddate>20151215</enddate><creator>Tala, Srinivasa R.</creator><creator>Schnell, Sathya M.</creator><creator>Haskell-Luevano, Carrie</creator><general>Elsevier Ltd</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><orcidid>https://orcid.org/0000-0002-6783-5972</orcidid></search><sort><creationdate>20151215</creationdate><title>Microwave-assisted solid-phase synthesis of side-chain to side-chain lactam-bridge cyclic peptides</title><author>Tala, Srinivasa R. ; Schnell, Sathya M. ; Haskell-Luevano, Carrie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c455t-a9e291502ec2da905b4d224b6c627629f560ae18ec0f0f2793ad7af815cc76823</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>alpha-MSH - analogs & derivatives</topic><topic>alpha-MSH - chemical synthesis</topic><topic>alpha-MSH - chemistry</topic><topic>alpha-MSH - metabolism</topic><topic>Animals</topic><topic>Cyclic peptides</topic><topic>Lactam-bridge cyclic peptides</topic><topic>Lactams - chemistry</topic><topic>Melanocyte-Stimulating Hormones - chemical synthesis</topic><topic>Melanocyte-Stimulating Hormones - chemistry</topic><topic>Melanocyte-Stimulating Hormones - metabolism</topic><topic>Mice</topic><topic>Microwave assisted synthesis</topic><topic>Microwaves</topic><topic>MTII</topic><topic>Peptides, Cyclic - chemical synthesis</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Protein Binding</topic><topic>Receptors, Melanocortin - antagonists & inhibitors</topic><topic>Receptors, Melanocortin - metabolism</topic><topic>SHU9119</topic><topic>Solid-Phase Synthesis Techniques</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tala, Srinivasa R.</creatorcontrib><creatorcontrib>Schnell, Sathya M.</creatorcontrib><creatorcontrib>Haskell-Luevano, Carrie</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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tala, Srinivasa R.</au><au>Schnell, Sathya M.</au><au>Haskell-Luevano, Carrie</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microwave-assisted solid-phase synthesis of side-chain to side-chain lactam-bridge cyclic peptides</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2015-12-15</date><risdate>2015</risdate><volume>25</volume><issue>24</issue><spage>5708</spage><epage>5711</epage><pages>5708-5711</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
Side-chain to side-chain lactam-bridged cyclic peptides have been utilized as therapeutic agents and biochemical tools. Previous synthetic methods of these peptides need special reaction conditions, form side products and take longer reaction times. Herein, an efficient microwave-assisted synthesis of side-chain to side-chain lactam-bridge cyclic peptides SHU9119 and MTII is reported. The synthesis time and efforts are significantly reduced in the present method, without side product formation. The analytical and pharmacological data of the synthesized cyclic peptides are in accordance with the commercially obtained compounds. This new method could be used to synthesize other side-chain to side-chain lactam-bridge peptides and amenable to automation and extensive SAR compound derivatization.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>26555357</pmid><doi>10.1016/j.bmcl.2015.10.095</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-6783-5972</orcidid><oa>free_for_read</oa></addata></record> |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | alpha-MSH - analogs & derivatives alpha-MSH - chemical synthesis alpha-MSH - chemistry alpha-MSH - metabolism Animals Cyclic peptides Lactam-bridge cyclic peptides Lactams - chemistry Melanocyte-Stimulating Hormones - chemical synthesis Melanocyte-Stimulating Hormones - chemistry Melanocyte-Stimulating Hormones - metabolism Mice Microwave assisted synthesis Microwaves MTII Peptides, Cyclic - chemical synthesis Peptides, Cyclic - chemistry Protein Binding Receptors, Melanocortin - antagonists & inhibitors Receptors, Melanocortin - metabolism SHU9119 Solid-Phase Synthesis Techniques |
| title | Microwave-assisted solid-phase synthesis of side-chain to side-chain lactam-bridge cyclic peptides |
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