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Synthesis and evaluation of eight-membered cyclic pseudo-dipeptides
In the course of the development of calpain inhibitors, we report the synthesis of eight-membered cyclic pseudo dipeptides closely related to the known inhibitor SJA6017. The ring closure was effected by metathesis of the diallyl-substituted dipeptides 6 and 7. The formation of the dipeptides under...
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| Published in: | Peptides (New York, N.Y. : 1980) N.Y. : 1980), 2005-02, Vol.26 (2), p.251-258 |
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| Main Authors: | , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c462t-ea4753bd297426f5e67a7594ceadb58173f41786338f962bbacb445704220a0f3 |
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| cites | cdi_FETCH-LOGICAL-c462t-ea4753bd297426f5e67a7594ceadb58173f41786338f962bbacb445704220a0f3 |
| container_end_page | 258 |
| container_issue | 2 |
| container_start_page | 251 |
| container_title | Peptides (New York, N.Y. : 1980) |
| container_volume | 26 |
| creator | Abell, Andrew D. Brown, Karina M. Coxon, James M. Jones, Matthew A. Miyamoto, Sigeru Neffe, Axel T. Nikkel, Janna M. Stuart, Blair G. |
| description | In the course of the development of calpain inhibitors, we report the synthesis of eight-membered cyclic pseudo dipeptides closely related to the known inhibitor SJA6017. The ring closure was effected by metathesis of the diallyl-substituted dipeptides
6 and
7. The formation of the dipeptides under kinetic control leads to the preferential formation of the
unlike diastereomer
7 over the
like diastereomer
6. The relative configuration of the diastereomers was determined by NMR and modeling studies of the related cyclic compounds
8 and
9 and their derivatives. The compounds proved not to inhibit calpain. |
| doi_str_mv | 10.1016/j.peptides.2004.09.006 |
| format | article |
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6 and
7. The formation of the dipeptides under kinetic control leads to the preferential formation of the
unlike diastereomer
7 over the
like diastereomer
6. The relative configuration of the diastereomers was determined by NMR and modeling studies of the related cyclic compounds
8 and
9 and their derivatives. The compounds proved not to inhibit calpain.</description><identifier>ISSN: 0196-9781</identifier><identifier>EISSN: 1873-5169</identifier><identifier>DOI: 10.1016/j.peptides.2004.09.006</identifier><identifier>PMID: 15629536</identifier><identifier>CODEN: PPTDD5</identifier><language>eng</language><publisher>New York, NY: Elsevier Inc</publisher><subject>Biological and medical sciences ; Calpain ; Calpain - antagonists & inhibitors ; Cataract ; Computational Biology ; Dipeptides - chemical synthesis ; Dipeptides - chemistry ; Fundamental and applied biological sciences. Psychology ; Lens diseases ; Medical sciences ; Metathesis ; Models, Molecular ; Molecular modeling ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Ophthalmology ; Peptides, Cyclic - chemical synthesis ; Peptides, Cyclic - chemistry ; Peptidomimetics ; Protein Conformation ; Vertebrates: endocrinology</subject><ispartof>Peptides (New York, N.Y. : 1980), 2005-02, Vol.26 (2), p.251-258</ispartof><rights>2004 Elsevier Inc.</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c462t-ea4753bd297426f5e67a7594ceadb58173f41786338f962bbacb445704220a0f3</citedby><cites>FETCH-LOGICAL-c462t-ea4753bd297426f5e67a7594ceadb58173f41786338f962bbacb445704220a0f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,786,790,27957,27958</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16530693$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15629536$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Abell, Andrew D.</creatorcontrib><creatorcontrib>Brown, Karina M.</creatorcontrib><creatorcontrib>Coxon, James M.</creatorcontrib><creatorcontrib>Jones, Matthew A.</creatorcontrib><creatorcontrib>Miyamoto, Sigeru</creatorcontrib><creatorcontrib>Neffe, Axel T.</creatorcontrib><creatorcontrib>Nikkel, Janna M.</creatorcontrib><creatorcontrib>Stuart, Blair G.</creatorcontrib><title>Synthesis and evaluation of eight-membered cyclic pseudo-dipeptides</title><title>Peptides (New York, N.Y. : 1980)</title><addtitle>Peptides</addtitle><description>In the course of the development of calpain inhibitors, we report the synthesis of eight-membered cyclic pseudo dipeptides closely related to the known inhibitor SJA6017. The ring closure was effected by metathesis of the diallyl-substituted dipeptides
6 and
7. The formation of the dipeptides under kinetic control leads to the preferential formation of the
unlike diastereomer
7 over the
like diastereomer
6. The relative configuration of the diastereomers was determined by NMR and modeling studies of the related cyclic compounds
8 and
9 and their derivatives. The compounds proved not to inhibit calpain.</description><subject>Biological and medical sciences</subject><subject>Calpain</subject><subject>Calpain - antagonists & inhibitors</subject><subject>Cataract</subject><subject>Computational Biology</subject><subject>Dipeptides - chemical synthesis</subject><subject>Dipeptides - chemistry</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Lens diseases</subject><subject>Medical sciences</subject><subject>Metathesis</subject><subject>Models, Molecular</subject><subject>Molecular modeling</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Ophthalmology</subject><subject>Peptides, Cyclic - chemical synthesis</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Peptidomimetics</subject><subject>Protein Conformation</subject><subject>Vertebrates: endocrinology</subject><issn>0196-9781</issn><issn>1873-5169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNqFkDtPwzAURi0EouXxF1AW2BLs-BVvoIqXhMQAzJZj34CrvLCTSv33pGpQRyYv57s-OghdEZwRTMTtOuuhH7yDmOUYswyrDGNxhJakkDTlRKhjtMREiVTJgizQWYxrPIFMFadoQbjIFadiiVbv23b4huhjYlqXwMbUoxl81yZdlYD_-h7SBpoSArjEbm3tbdJHGF2XOv9ncIFOKlNHuJzfc_T5-PCxek5f355eVvevqWUiH1IwTHJaulxJlouKg5BGcsUsGFfygkhaMSILQWlRKZGXpbElY1xilufY4Iqeo5v93T50PyPEQTc-Wqhr00I3Ri3kNFWYTqDYgzZ0MQaodB98Y8JWE6x3-fRa_8nrXT6NlZ7yTcOr-YexbMAdZnOvCbieAROtqatgWuvjgROcYqF2Bnd7DqYeGw9BR-uhteB8ADto1_n_XH4BI5mRYw</recordid><startdate>20050201</startdate><enddate>20050201</enddate><creator>Abell, Andrew D.</creator><creator>Brown, Karina M.</creator><creator>Coxon, James M.</creator><creator>Jones, Matthew A.</creator><creator>Miyamoto, Sigeru</creator><creator>Neffe, Axel T.</creator><creator>Nikkel, Janna M.</creator><creator>Stuart, Blair G.</creator><general>Elsevier Inc</general><general>Elsevier Science</general><scope>IQODW</scope><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>20050201</creationdate><title>Synthesis and evaluation of eight-membered cyclic pseudo-dipeptides</title><author>Abell, Andrew D. ; Brown, Karina M. ; Coxon, James M. ; Jones, Matthew A. ; Miyamoto, Sigeru ; Neffe, Axel T. ; Nikkel, Janna M. ; Stuart, Blair G.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c462t-ea4753bd297426f5e67a7594ceadb58173f41786338f962bbacb445704220a0f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Biological and medical sciences</topic><topic>Calpain</topic><topic>Calpain - antagonists & inhibitors</topic><topic>Cataract</topic><topic>Computational Biology</topic><topic>Dipeptides - chemical synthesis</topic><topic>Dipeptides - chemistry</topic><topic>Fundamental and applied biological sciences. 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The ring closure was effected by metathesis of the diallyl-substituted dipeptides
6 and
7. The formation of the dipeptides under kinetic control leads to the preferential formation of the
unlike diastereomer
7 over the
like diastereomer
6. The relative configuration of the diastereomers was determined by NMR and modeling studies of the related cyclic compounds
8 and
9 and their derivatives. The compounds proved not to inhibit calpain.</abstract><cop>New York, NY</cop><pub>Elsevier Inc</pub><pmid>15629536</pmid><doi>10.1016/j.peptides.2004.09.006</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0196-9781 |
| ispartof | Peptides (New York, N.Y. : 1980), 2005-02, Vol.26 (2), p.251-258 |
| issn | 0196-9781 1873-5169 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_67338903 |
| source | ScienceDirect Journals |
| subjects | Biological and medical sciences Calpain Calpain - antagonists & inhibitors Cataract Computational Biology Dipeptides - chemical synthesis Dipeptides - chemistry Fundamental and applied biological sciences. Psychology Lens diseases Medical sciences Metathesis Models, Molecular Molecular modeling Molecular Structure Nuclear Magnetic Resonance, Biomolecular Ophthalmology Peptides, Cyclic - chemical synthesis Peptides, Cyclic - chemistry Peptidomimetics Protein Conformation Vertebrates: endocrinology |
| title | Synthesis and evaluation of eight-membered cyclic pseudo-dipeptides |
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