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Formation of mononuclear and chloro-bridged binuclear copper(II) complexes of patellamide D, a naturally occurring cyclic peptide: influence of anion and solvent
Patellamide D (patH 4) is a cyclic octapeptide isolated from the ascidian Lissoclinum patella. The peptide possesses a 24-azacrown-8 macrocyclic structure containing two oxazoline and two thiazole rings, each separated by an amino acid. The present spectrophotometric, electron paramagnetic resonance...
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| Published in: | Journal of inorganic biochemistry 2004-11, Vol.98 (11), p.1857-1866 |
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| Main Authors: | , , , , , , |
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| cites | cdi_FETCH-LOGICAL-c367t-bcf53b21a17bf71c33dbb6c281dbf3fd6ab75c51aa5f07f7ce1a8a4f06194dcc3 |
| container_end_page | 1866 |
| container_issue | 11 |
| container_start_page | 1857 |
| container_title | Journal of inorganic biochemistry |
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| creator | van den Brenk, Anna L. Tyndall, Joel D.A. Cusack, Rodney M. Jones, Alun Fairlie, David P. Gahan, Lawrence R. Hanson, Graeme R. |
| description | Patellamide D (patH
4) is a cyclic octapeptide isolated from the ascidian
Lissoclinum patella. The peptide possesses a 24-azacrown-8 macrocyclic structure containing two oxazoline and two thiazole rings, each separated by an amino acid. The present spectrophotometric, electron paramagnetic resonance (EPR) and mass spectral studies show that patellamide D reacts with CuCl
2 and triethylamine in acetonitrile to form mononuclear and binuclear copper(II) complexes containing chloride. Molecular modelling and EPR studies suggest that the chloride anion bridges the copper(II) ions in the binuclear complex [Cu
2(patH
2)(μ-Cl)]
+. These results contrast with a previous study employing both base and methanol, the latter substituting for chloride in the copper(II) complexes en route to the stable μ-carbonato binuclear copper(II) complex [Cu
2 (patH
2)(μ-CO
3)]. Solvent clearly plays an important role in both stabilising these metal ion complexes and influencing their chemical reactivities. |
| doi_str_mv | 10.1016/j.jinorgbio.2004.08.005 |
| format | article |
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4) is a cyclic octapeptide isolated from the ascidian
Lissoclinum patella. The peptide possesses a 24-azacrown-8 macrocyclic structure containing two oxazoline and two thiazole rings, each separated by an amino acid. The present spectrophotometric, electron paramagnetic resonance (EPR) and mass spectral studies show that patellamide D reacts with CuCl
2 and triethylamine in acetonitrile to form mononuclear and binuclear copper(II) complexes containing chloride. Molecular modelling and EPR studies suggest that the chloride anion bridges the copper(II) ions in the binuclear complex [Cu
2(patH
2)(μ-Cl)]
+. These results contrast with a previous study employing both base and methanol, the latter substituting for chloride in the copper(II) complexes en route to the stable μ-carbonato binuclear copper(II) complex [Cu
2 (patH
2)(μ-CO
3)]. Solvent clearly plays an important role in both stabilising these metal ion complexes and influencing their chemical reactivities.</description><identifier>ISSN: 0162-0134</identifier><identifier>EISSN: 1873-3344</identifier><identifier>DOI: 10.1016/j.jinorgbio.2004.08.005</identifier><identifier>PMID: 15522413</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Animals ; Anions ; Circular Dichroism ; Copper - chemistry ; Copper(II) complexes ; Electron Spin Resonance Spectroscopy ; EPR ; Marine cyclic peptides ; Models, Molecular ; Molecular Conformation ; Patellamide D ; Peptides, Cyclic - chemistry ; Peptides, Cyclic - isolation & purification ; Solvents ; Spectrophotometry ; Urochordata - chemistry</subject><ispartof>Journal of inorganic biochemistry, 2004-11, Vol.98 (11), p.1857-1866</ispartof><rights>2004 Elsevier Inc.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c367t-bcf53b21a17bf71c33dbb6c281dbf3fd6ab75c51aa5f07f7ce1a8a4f06194dcc3</citedby><cites>FETCH-LOGICAL-c367t-bcf53b21a17bf71c33dbb6c281dbf3fd6ab75c51aa5f07f7ce1a8a4f06194dcc3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15522413$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>van den Brenk, Anna L.</creatorcontrib><creatorcontrib>Tyndall, Joel D.A.</creatorcontrib><creatorcontrib>Cusack, Rodney M.</creatorcontrib><creatorcontrib>Jones, Alun</creatorcontrib><creatorcontrib>Fairlie, David P.</creatorcontrib><creatorcontrib>Gahan, Lawrence R.</creatorcontrib><creatorcontrib>Hanson, Graeme R.</creatorcontrib><title>Formation of mononuclear and chloro-bridged binuclear copper(II) complexes of patellamide D, a naturally occurring cyclic peptide: influence of anion and solvent</title><title>Journal of inorganic biochemistry</title><addtitle>J Inorg Biochem</addtitle><description>Patellamide D (patH
4) is a cyclic octapeptide isolated from the ascidian
Lissoclinum patella. The peptide possesses a 24-azacrown-8 macrocyclic structure containing two oxazoline and two thiazole rings, each separated by an amino acid. The present spectrophotometric, electron paramagnetic resonance (EPR) and mass spectral studies show that patellamide D reacts with CuCl
2 and triethylamine in acetonitrile to form mononuclear and binuclear copper(II) complexes containing chloride. Molecular modelling and EPR studies suggest that the chloride anion bridges the copper(II) ions in the binuclear complex [Cu
2(patH
2)(μ-Cl)]
+. These results contrast with a previous study employing both base and methanol, the latter substituting for chloride in the copper(II) complexes en route to the stable μ-carbonato binuclear copper(II) complex [Cu
2 (patH
2)(μ-CO
3)]. Solvent clearly plays an important role in both stabilising these metal ion complexes and influencing their chemical reactivities.</description><subject>Animals</subject><subject>Anions</subject><subject>Circular Dichroism</subject><subject>Copper - chemistry</subject><subject>Copper(II) complexes</subject><subject>Electron Spin Resonance Spectroscopy</subject><subject>EPR</subject><subject>Marine cyclic peptides</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Patellamide D</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Peptides, Cyclic - isolation & purification</subject><subject>Solvents</subject><subject>Spectrophotometry</subject><subject>Urochordata - chemistry</subject><issn>0162-0134</issn><issn>1873-3344</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNqFkcFu1DAQhi0EotvCK4BPCCQS7NhJFm5VaWGlSlzgbNnj8eKVYwc7qdjH4U1JtAscOY2l-eb_PfMT8pKzmjPevTvUBx9T3huf6oYxWbNtzVj7iGz4theVEFI-JpuFbCrGhbwgl6Uc2EK0sn9KLnjbNo3kYkN-3aU86MmnSJOjQ4opzhBQZ6qjpfA9pJwqk73do6XG_2lCGkfMr3e7N8tzGAP-xLIKjHrCEPTgLdKPb6mmUU9z1iEcaQKYc_ZxT-EIwQMdcZwW7gP10YUZI-CqoOP6l9W8pPCAcXpGnjgdCj4_1yvy7e72683n6v7Lp93N9X0FouunyoBrhWm45r1xPQchrDEdNFtujRPOdtr0LbRc69ax3vWAXG-1dKzj76UFEFfk1Ul3zOnHjGVSgy-wbhMxzUV1PZOMS7GA_QmEnErJ6NSY_aDzUXGm1nTUQf1NR63pKLZVy-2XyRdni9kMaP_NneNYgOsTgMuiDx6zKuDXy1ifESZlk_-vyW9TOanO</recordid><startdate>20041101</startdate><enddate>20041101</enddate><creator>van den Brenk, Anna L.</creator><creator>Tyndall, Joel D.A.</creator><creator>Cusack, Rodney M.</creator><creator>Jones, Alun</creator><creator>Fairlie, David P.</creator><creator>Gahan, Lawrence R.</creator><creator>Hanson, Graeme R.</creator><general>Elsevier Inc</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></search><sort><creationdate>20041101</creationdate><title>Formation of mononuclear and chloro-bridged binuclear copper(II) complexes of patellamide D, a naturally occurring cyclic peptide: influence of anion and solvent</title><author>van den Brenk, Anna L. ; Tyndall, Joel D.A. ; Cusack, Rodney M. ; Jones, Alun ; Fairlie, David P. ; Gahan, Lawrence R. ; Hanson, Graeme R.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c367t-bcf53b21a17bf71c33dbb6c281dbf3fd6ab75c51aa5f07f7ce1a8a4f06194dcc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Animals</topic><topic>Anions</topic><topic>Circular Dichroism</topic><topic>Copper - chemistry</topic><topic>Copper(II) complexes</topic><topic>Electron Spin Resonance Spectroscopy</topic><topic>EPR</topic><topic>Marine cyclic peptides</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Patellamide D</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Peptides, Cyclic - isolation & purification</topic><topic>Solvents</topic><topic>Spectrophotometry</topic><topic>Urochordata - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>van den Brenk, Anna L.</creatorcontrib><creatorcontrib>Tyndall, Joel D.A.</creatorcontrib><creatorcontrib>Cusack, Rodney M.</creatorcontrib><creatorcontrib>Jones, Alun</creatorcontrib><creatorcontrib>Fairlie, David P.</creatorcontrib><creatorcontrib>Gahan, Lawrence R.</creatorcontrib><creatorcontrib>Hanson, Graeme R.</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>Journal of inorganic biochemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>van den Brenk, Anna L.</au><au>Tyndall, Joel D.A.</au><au>Cusack, Rodney M.</au><au>Jones, Alun</au><au>Fairlie, David P.</au><au>Gahan, Lawrence R.</au><au>Hanson, Graeme R.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Formation of mononuclear and chloro-bridged binuclear copper(II) complexes of patellamide D, a naturally occurring cyclic peptide: influence of anion and solvent</atitle><jtitle>Journal of inorganic biochemistry</jtitle><addtitle>J Inorg Biochem</addtitle><date>2004-11-01</date><risdate>2004</risdate><volume>98</volume><issue>11</issue><spage>1857</spage><epage>1866</epage><pages>1857-1866</pages><issn>0162-0134</issn><eissn>1873-3344</eissn><abstract>Patellamide D (patH
4) is a cyclic octapeptide isolated from the ascidian
Lissoclinum patella. The peptide possesses a 24-azacrown-8 macrocyclic structure containing two oxazoline and two thiazole rings, each separated by an amino acid. The present spectrophotometric, electron paramagnetic resonance (EPR) and mass spectral studies show that patellamide D reacts with CuCl
2 and triethylamine in acetonitrile to form mononuclear and binuclear copper(II) complexes containing chloride. Molecular modelling and EPR studies suggest that the chloride anion bridges the copper(II) ions in the binuclear complex [Cu
2(patH
2)(μ-Cl)]
+. These results contrast with a previous study employing both base and methanol, the latter substituting for chloride in the copper(II) complexes en route to the stable μ-carbonato binuclear copper(II) complex [Cu
2 (patH
2)(μ-CO
3)]. Solvent clearly plays an important role in both stabilising these metal ion complexes and influencing their chemical reactivities.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>15522413</pmid><doi>10.1016/j.jinorgbio.2004.08.005</doi><tpages>10</tpages></addata></record> |
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| ispartof | Journal of inorganic biochemistry, 2004-11, Vol.98 (11), p.1857-1866 |
| issn | 0162-0134 1873-3344 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_67040143 |
| source | ScienceDirect Journals |
| subjects | Animals Anions Circular Dichroism Copper - chemistry Copper(II) complexes Electron Spin Resonance Spectroscopy EPR Marine cyclic peptides Models, Molecular Molecular Conformation Patellamide D Peptides, Cyclic - chemistry Peptides, Cyclic - isolation & purification Solvents Spectrophotometry Urochordata - chemistry |
| title | Formation of mononuclear and chloro-bridged binuclear copper(II) complexes of patellamide D, a naturally occurring cyclic peptide: influence of anion and solvent |
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