Two novel solvent system compositions for protected synthetic peptide purification by centrifugal partition chromatography
•Purification of hydrophobic protected peptides by centrifugal partition chromatography.•Synthetic intermediates of API'S.•Development of new biphasic solvent systems.•Efficiency of co-current and elution-extrusion modes. Protected synthetic peptide intermediates are often hydrophobic and not s...
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| Veröffentlicht in: | Journal of Chromatography A 2014-04, Vol.1337, p.155-161 |
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| container_title | Journal of Chromatography A |
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| creator | Amarouche, Nassima Giraud, Matthieu Forni, Luciano Butte, Alessandro Edwards, F. Borie, Nicolas Renault, Jean-Hugues |
| description | •Purification of hydrophobic protected peptides by centrifugal partition chromatography.•Synthetic intermediates of API'S.•Development of new biphasic solvent systems.•Efficiency of co-current and elution-extrusion modes.
Protected synthetic peptide intermediates are often hydrophobic and not soluble in most common solvents. They are thus difficult to purify by preparative reversed-phase high-performance liquid chromatography (RP-HPLC), usually used for industrial production. It is then challenging to develop alternative chromatographic purification processes. Support-free liquid–liquid chromatographic techniques, including both hydrostatic (centrifugal partition chromatography or CPC) and hydrodynamic (counter-current chromatography or CCC) devices, are mainly involved in phytochemical studies but have also been applied to synthetic peptide purification. In this framework, two new biphasic solvent system compositions covering a wide range of polarity were developed to overcome solubility problems mentioned above. The new systems composed of heptane/tetrahydrofuran/acetonitrile/dimethylsulfoxide/water and heptane/methyl-tetrahydrofuran/N-methylpyrrolidone/water were efficiently used for the CPC purification of a 39-mer protected exenatide (Byetta®) and a 8-mer protected peptide intermediate of bivalirudin (Angiox®) synthesis. Phase compositions of the different biphasic solvent systems were determined by 1H nuclear magnetic resonance. Physico-chemical properties including viscosity, density and interfacial tension of these biphasic systems are also described. |
| doi_str_mv | 10.1016/j.chroma.2014.02.052 |
| format | Article |
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Protected synthetic peptide intermediates are often hydrophobic and not soluble in most common solvents. They are thus difficult to purify by preparative reversed-phase high-performance liquid chromatography (RP-HPLC), usually used for industrial production. It is then challenging to develop alternative chromatographic purification processes. Support-free liquid–liquid chromatographic techniques, including both hydrostatic (centrifugal partition chromatography or CPC) and hydrodynamic (counter-current chromatography or CCC) devices, are mainly involved in phytochemical studies but have also been applied to synthetic peptide purification. In this framework, two new biphasic solvent system compositions covering a wide range of polarity were developed to overcome solubility problems mentioned above. The new systems composed of heptane/tetrahydrofuran/acetonitrile/dimethylsulfoxide/water and heptane/methyl-tetrahydrofuran/N-methylpyrrolidone/water were efficiently used for the CPC purification of a 39-mer protected exenatide (Byetta®) and a 8-mer protected peptide intermediate of bivalirudin (Angiox®) synthesis. Phase compositions of the different biphasic solvent systems were determined by 1H nuclear magnetic resonance. Physico-chemical properties including viscosity, density and interfacial tension of these biphasic systems are also described.</description><identifier>ISSN: 0021-9673</identifier><identifier>EISSN: 1873-3778</identifier><identifier>DOI: 10.1016/j.chroma.2014.02.052</identifier><identifier>PMID: 24630060</identifier><identifier>CODEN: JOCRAM</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Aminoacids, peptides. Hormones. Neuropeptides ; Analytical chemistry ; Analytical, structural and metabolic biochemistry ; Biological and medical sciences ; Biphasic solvent systems ; centrifugal partition chromatography (CPC) ; Chemical Sciences ; Chemistry ; Chromatographic methods and physical methods associated with chromatography ; Countercurrent Distribution - methods ; Exact sciences and technology ; Fundamental and applied biological sciences. Psychology ; Hirudins - isolation & purification ; Life Sciences ; Magnetic Resonance Spectroscopy ; Organic chemistry ; Other chromatographic methods ; Peptide Fragments - isolation & purification ; Peptides - isolation & purification ; Pharmaceutical sciences ; preparative chromatography ; protected peptides ; Proteins ; Recombinant Proteins - isolation & purification ; Solubility ; Solvents - chemistry ; Venoms - isolation & purification</subject><ispartof>Journal of Chromatography A, 2014-04, Vol.1337, p.155-161</ispartof><rights>2014 Elsevier B.V.</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2014 Elsevier B.V. All rights reserved.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c505t-a607ee0554acf619319bb95efd49c6db22e68fadff59bc5b948b99ab213762173</citedby><cites>FETCH-LOGICAL-c505t-a607ee0554acf619319bb95efd49c6db22e68fadff59bc5b948b99ab213762173</cites><orcidid>0000-0002-1208-9677 ; 0000-0002-8705-7258</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.chroma.2014.02.052$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=28313180$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24630060$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-01968791$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Amarouche, Nassima</creatorcontrib><creatorcontrib>Giraud, Matthieu</creatorcontrib><creatorcontrib>Forni, Luciano</creatorcontrib><creatorcontrib>Butte, Alessandro</creatorcontrib><creatorcontrib>Edwards, F.</creatorcontrib><creatorcontrib>Borie, Nicolas</creatorcontrib><creatorcontrib>Renault, Jean-Hugues</creatorcontrib><title>Two novel solvent system compositions for protected synthetic peptide purification by centrifugal partition chromatography</title><title>Journal of Chromatography A</title><addtitle>J Chromatogr A</addtitle><description>•Purification of hydrophobic protected peptides by centrifugal partition chromatography.•Synthetic intermediates of API'S.•Development of new biphasic solvent systems.•Efficiency of co-current and elution-extrusion modes.
Protected synthetic peptide intermediates are often hydrophobic and not soluble in most common solvents. They are thus difficult to purify by preparative reversed-phase high-performance liquid chromatography (RP-HPLC), usually used for industrial production. It is then challenging to develop alternative chromatographic purification processes. Support-free liquid–liquid chromatographic techniques, including both hydrostatic (centrifugal partition chromatography or CPC) and hydrodynamic (counter-current chromatography or CCC) devices, are mainly involved in phytochemical studies but have also been applied to synthetic peptide purification. In this framework, two new biphasic solvent system compositions covering a wide range of polarity were developed to overcome solubility problems mentioned above. The new systems composed of heptane/tetrahydrofuran/acetonitrile/dimethylsulfoxide/water and heptane/methyl-tetrahydrofuran/N-methylpyrrolidone/water were efficiently used for the CPC purification of a 39-mer protected exenatide (Byetta®) and a 8-mer protected peptide intermediate of bivalirudin (Angiox®) synthesis. Phase compositions of the different biphasic solvent systems were determined by 1H nuclear magnetic resonance. Physico-chemical properties including viscosity, density and interfacial tension of these biphasic systems are also described.</description><subject>Aminoacids, peptides. Hormones. Neuropeptides</subject><subject>Analytical chemistry</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>Biological and medical sciences</subject><subject>Biphasic solvent systems</subject><subject>centrifugal partition chromatography (CPC)</subject><subject>Chemical Sciences</subject><subject>Chemistry</subject><subject>Chromatographic methods and physical methods associated with chromatography</subject><subject>Countercurrent Distribution - methods</subject><subject>Exact sciences and technology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hirudins - isolation & purification</subject><subject>Life Sciences</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Organic chemistry</subject><subject>Other chromatographic methods</subject><subject>Peptide Fragments - isolation & purification</subject><subject>Peptides - isolation & purification</subject><subject>Pharmaceutical sciences</subject><subject>preparative chromatography</subject><subject>protected peptides</subject><subject>Proteins</subject><subject>Recombinant Proteins - isolation & purification</subject><subject>Solubility</subject><subject>Solvents - chemistry</subject><subject>Venoms - isolation & purification</subject><issn>0021-9673</issn><issn>1873-3778</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kc-L1DAUx4Mo7rj6H4jkIuihNT_apLkIy6KuMOBlPYc0fd3J0DY1SUfGv97UjuvNU-DxeZ-8974IvaakpISKD8fSHoIfTckIrUrCSlKzJ2hHG8kLLmXzFO0IYbRQQvIr9CLGIyFUEsmeoytWCU6IIDv06_6nx5M_wYCjH04wJRzPMcGIrR9nH11yfoq49wHPwSewCbpMTOkAyVk8w5xcB3heguudNSuN2zO2WZQry4MZ8GxC-qPB28DJPwQzH84v0bPeDBFeXd5r9P3zp_vbu2L_7cvX25t9YWtSp8IIIgFIXVfG9oIqTlXbqhr6rlJWdC1jIJredH1fq9bWraqaVinTMsqlYFTya_R-8x7MoOfgRhPO2hun7272eq0RqkQjFT3RzL7b2LzsjwVi0qOLFobBTOCXqKngNWGsaVZttaE2-BgD9I9uSvSakD7qbWG9JqQJ0zmh3Pbm8sPSjtA9Nv2NJANvL4CJ1gx9MJN18R_XcMpps3IfNw7y7U4Ogo7WwWShcyHHpDvv_j_Jb42Bs-k</recordid><startdate>20140411</startdate><enddate>20140411</enddate><creator>Amarouche, Nassima</creator><creator>Giraud, Matthieu</creator><creator>Forni, Luciano</creator><creator>Butte, Alessandro</creator><creator>Edwards, F.</creator><creator>Borie, Nicolas</creator><creator>Renault, Jean-Hugues</creator><general>Elsevier B.V</general><general>Elsevier</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>7QH</scope><scope>7UA</scope><scope>C1K</scope><scope>F1W</scope><scope>H97</scope><scope>L.G</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-1208-9677</orcidid><orcidid>https://orcid.org/0000-0002-8705-7258</orcidid></search><sort><creationdate>20140411</creationdate><title>Two novel solvent system compositions for protected synthetic peptide purification by centrifugal partition chromatography</title><author>Amarouche, Nassima ; Giraud, Matthieu ; Forni, Luciano ; Butte, Alessandro ; Edwards, F. ; Borie, Nicolas ; Renault, Jean-Hugues</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c505t-a607ee0554acf619319bb95efd49c6db22e68fadff59bc5b948b99ab213762173</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Aminoacids, peptides. Hormones. Neuropeptides</topic><topic>Analytical chemistry</topic><topic>Analytical, structural and metabolic biochemistry</topic><topic>Biological and medical sciences</topic><topic>Biphasic solvent systems</topic><topic>centrifugal partition chromatography (CPC)</topic><topic>Chemical Sciences</topic><topic>Chemistry</topic><topic>Chromatographic methods and physical methods associated with chromatography</topic><topic>Countercurrent Distribution - methods</topic><topic>Exact sciences and technology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Hirudins - isolation & purification</topic><topic>Life Sciences</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Organic chemistry</topic><topic>Other chromatographic methods</topic><topic>Peptide Fragments - isolation & purification</topic><topic>Peptides - isolation & purification</topic><topic>Pharmaceutical sciences</topic><topic>preparative chromatography</topic><topic>protected peptides</topic><topic>Proteins</topic><topic>Recombinant Proteins - isolation & purification</topic><topic>Solubility</topic><topic>Solvents - chemistry</topic><topic>Venoms - isolation & purification</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Amarouche, Nassima</creatorcontrib><creatorcontrib>Giraud, Matthieu</creatorcontrib><creatorcontrib>Forni, Luciano</creatorcontrib><creatorcontrib>Butte, Alessandro</creatorcontrib><creatorcontrib>Edwards, F.</creatorcontrib><creatorcontrib>Borie, Nicolas</creatorcontrib><creatorcontrib>Renault, Jean-Hugues</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Aqualine</collection><collection>Water Resources Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 3: Aquatic Pollution & Environmental Quality</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Journal of Chromatography A</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Amarouche, Nassima</au><au>Giraud, Matthieu</au><au>Forni, Luciano</au><au>Butte, Alessandro</au><au>Edwards, F.</au><au>Borie, Nicolas</au><au>Renault, Jean-Hugues</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Two novel solvent system compositions for protected synthetic peptide purification by centrifugal partition chromatography</atitle><jtitle>Journal of Chromatography A</jtitle><addtitle>J Chromatogr A</addtitle><date>2014-04-11</date><risdate>2014</risdate><volume>1337</volume><spage>155</spage><epage>161</epage><pages>155-161</pages><issn>0021-9673</issn><eissn>1873-3778</eissn><coden>JOCRAM</coden><abstract>•Purification of hydrophobic protected peptides by centrifugal partition chromatography.•Synthetic intermediates of API'S.•Development of new biphasic solvent systems.•Efficiency of co-current and elution-extrusion modes.
Protected synthetic peptide intermediates are often hydrophobic and not soluble in most common solvents. They are thus difficult to purify by preparative reversed-phase high-performance liquid chromatography (RP-HPLC), usually used for industrial production. It is then challenging to develop alternative chromatographic purification processes. Support-free liquid–liquid chromatographic techniques, including both hydrostatic (centrifugal partition chromatography or CPC) and hydrodynamic (counter-current chromatography or CCC) devices, are mainly involved in phytochemical studies but have also been applied to synthetic peptide purification. In this framework, two new biphasic solvent system compositions covering a wide range of polarity were developed to overcome solubility problems mentioned above. The new systems composed of heptane/tetrahydrofuran/acetonitrile/dimethylsulfoxide/water and heptane/methyl-tetrahydrofuran/N-methylpyrrolidone/water were efficiently used for the CPC purification of a 39-mer protected exenatide (Byetta®) and a 8-mer protected peptide intermediate of bivalirudin (Angiox®) synthesis. Phase compositions of the different biphasic solvent systems were determined by 1H nuclear magnetic resonance. Physico-chemical properties including viscosity, density and interfacial tension of these biphasic systems are also described.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><pmid>24630060</pmid><doi>10.1016/j.chroma.2014.02.052</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-1208-9677</orcidid><orcidid>https://orcid.org/0000-0002-8705-7258</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Aminoacids, peptides. Hormones. Neuropeptides Analytical chemistry Analytical, structural and metabolic biochemistry Biological and medical sciences Biphasic solvent systems centrifugal partition chromatography (CPC) Chemical Sciences Chemistry Chromatographic methods and physical methods associated with chromatography Countercurrent Distribution - methods Exact sciences and technology Fundamental and applied biological sciences. Psychology Hirudins - isolation & purification Life Sciences Magnetic Resonance Spectroscopy Organic chemistry Other chromatographic methods Peptide Fragments - isolation & purification Peptides - isolation & purification Pharmaceutical sciences preparative chromatography protected peptides Proteins Recombinant Proteins - isolation & purification Solubility Solvents - chemistry Venoms - isolation & purification |
| title | Two novel solvent system compositions for protected synthetic peptide purification by centrifugal partition chromatography |
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