Microwave-assisted Boc-solid phase peptide synthesis of cyclic cysteine-rich peptides

In this study we describe the first protocols for the synthesis of cystine‐rich peptides in the presence of microwave radiation with Boc‐solid phase peptide synthesis (SPPS). This method is exemplified for macrocyclic peptides known as cyclotides, which comprise ∼30 amino acids and incorporate a cys...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Journal of peptide science 2008-06, Vol.14 (6), p.683-689
Hauptverfasser:	Čemažar, Maša, Craik, David J.
Format:	Artikel
Sprache:	eng
Schlagworte:	Boc-SPPS Chromatography, High Pressure Liquid circular protein Cysteine - chemistry cystine knot microwave Microwaves native chemical ligation Peptides - chemical synthesis
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	689
container_issue	6
container_start_page	683
container_title	Journal of peptide science
container_volume	14
creator	Čemažar, Maša Craik, David J.
description	In this study we describe the first protocols for the synthesis of cystine‐rich peptides in the presence of microwave radiation with Boc‐solid phase peptide synthesis (SPPS). This method is exemplified for macrocyclic peptides known as cyclotides, which comprise ∼30 amino acids and incorporate a cystine knot arrangement of their three disulfide bonds. However, the method is broadly applicable for a wide range of peptides using Boc‐SPPS, especially for SPPS of large peptides via native chemical ligation. Microwave radiation produces peptides in high yield and with high purity, and we were able to reduce the time for the assembly of ∼30 mer peptide chains to an overnight reaction in the automated microwave‐assisted synthesis. Copyright © 2007 European Peptide Society and John Wiley & Sons, Ltd.
doi_str_mv	10.1002/psc.972
format	Article
fullrecord	<record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_70759447</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>21127826</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4502-65d9a601a66ea355b69824d59f60cabea0545b57e5f6aecc1f6ecdfb9219d9103</originalsourceid><addsrcrecordid>eNqF0clOwzAQBmALgWhZxBugnOCADLYT2_ERKihLWcQiJC6W40xUQ9qEuKX07XGVAifEaUaaz__hN0I7lBxSQthR7e2hkmwFdSlRCtM4lauLXXLMBJUdtOH9KyHhxsU66tCUJElKRRc9XTvbVDPzAdh47_wE8uiksthXpcujemg8RDXUE5dD5OfjyRACiqoisnNbOhtGeOLGgBtnh9_Sb6G1wpQetpdzEz2dnT72zvHgtn_ROx5gm3DCsOC5MoJQIwSYmPNMqJQlOVeFINZkYAhPeMYl8EIYsJYWAmxeZIpRlStK4k201-bWTfU-BT_RI-ctlKUZQzX1WoYCVJLIfyGjlMmUiQD3Wxha8b6BQteNG5lmrinRi6p1qFqHqoPcXUZOsxHkv27ZbQAHLZi5EuZ_5ei7h14bh1u9-IPPH22aNy1kLLl-vunrF3Z1fzmIqb6LvwA0e5dw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>21127826</pqid></control><display><type>article</type><title>Microwave-assisted Boc-solid phase peptide synthesis of cyclic cysteine-rich peptides</title><source>MEDLINE</source><source>Wiley Online Library Journals Frontfile Complete</source><creator>Čemažar, Maša ; Craik, David J.</creator><creatorcontrib>Čemažar, Maša ; Craik, David J.</creatorcontrib><description>In this study we describe the first protocols for the synthesis of cystine‐rich peptides in the presence of microwave radiation with Boc‐solid phase peptide synthesis (SPPS). This method is exemplified for macrocyclic peptides known as cyclotides, which comprise ∼30 amino acids and incorporate a cystine knot arrangement of their three disulfide bonds. However, the method is broadly applicable for a wide range of peptides using Boc‐SPPS, especially for SPPS of large peptides via native chemical ligation. Microwave radiation produces peptides in high yield and with high purity, and we were able to reduce the time for the assembly of ∼30 mer peptide chains to an overnight reaction in the automated microwave‐assisted synthesis. Copyright © 2007 European Peptide Society and John Wiley & Sons, Ltd.</description><identifier>ISSN: 1075-2617</identifier><identifier>EISSN: 1099-1387</identifier><identifier>DOI: 10.1002/psc.972</identifier><identifier>PMID: 18044816</identifier><language>eng</language><publisher>Chichester, UK: John Wiley & Sons, Ltd</publisher><subject>Boc-SPPS ; Chromatography, High Pressure Liquid ; circular protein ; Cysteine - chemistry ; cystine knot ; microwave ; Microwaves ; native chemical ligation ; Peptides - chemical synthesis</subject><ispartof>Journal of peptide science, 2008-06, Vol.14 (6), p.683-689</ispartof><rights>Copyright © 2007 European Peptide Society and John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4502-65d9a601a66ea355b69824d59f60cabea0545b57e5f6aecc1f6ecdfb9219d9103</citedby><cites>FETCH-LOGICAL-c4502-65d9a601a66ea355b69824d59f60cabea0545b57e5f6aecc1f6ecdfb9219d9103</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fpsc.972$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fpsc.972$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18044816$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Čemažar, Maša</creatorcontrib><creatorcontrib>Craik, David J.</creatorcontrib><title>Microwave-assisted Boc-solid phase peptide synthesis of cyclic cysteine-rich peptides</title><title>Journal of peptide science</title><addtitle>J. Peptide Sci</addtitle><description>In this study we describe the first protocols for the synthesis of cystine‐rich peptides in the presence of microwave radiation with Boc‐solid phase peptide synthesis (SPPS). This method is exemplified for macrocyclic peptides known as cyclotides, which comprise ∼30 amino acids and incorporate a cystine knot arrangement of their three disulfide bonds. However, the method is broadly applicable for a wide range of peptides using Boc‐SPPS, especially for SPPS of large peptides via native chemical ligation. Microwave radiation produces peptides in high yield and with high purity, and we were able to reduce the time for the assembly of ∼30 mer peptide chains to an overnight reaction in the automated microwave‐assisted synthesis. Copyright © 2007 European Peptide Society and John Wiley & Sons, Ltd.</description><subject>Boc-SPPS</subject><subject>Chromatography, High Pressure Liquid</subject><subject>circular protein</subject><subject>Cysteine - chemistry</subject><subject>cystine knot</subject><subject>microwave</subject><subject>Microwaves</subject><subject>native chemical ligation</subject><subject>Peptides - chemical synthesis</subject><issn>1075-2617</issn><issn>1099-1387</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0clOwzAQBmALgWhZxBugnOCADLYT2_ERKihLWcQiJC6W40xUQ9qEuKX07XGVAifEaUaaz__hN0I7lBxSQthR7e2hkmwFdSlRCtM4lauLXXLMBJUdtOH9KyHhxsU66tCUJElKRRc9XTvbVDPzAdh47_wE8uiksthXpcujemg8RDXUE5dD5OfjyRACiqoisnNbOhtGeOLGgBtnh9_Sb6G1wpQetpdzEz2dnT72zvHgtn_ROx5gm3DCsOC5MoJQIwSYmPNMqJQlOVeFINZkYAhPeMYl8EIYsJYWAmxeZIpRlStK4k201-bWTfU-BT_RI-ctlKUZQzX1WoYCVJLIfyGjlMmUiQD3Wxha8b6BQteNG5lmrinRi6p1qFqHqoPcXUZOsxHkv27ZbQAHLZi5EuZ_5ei7h14bh1u9-IPPH22aNy1kLLl-vunrF3Z1fzmIqb6LvwA0e5dw</recordid><startdate>200806</startdate><enddate>200806</enddate><creator>Čemažar, Maša</creator><creator>Craik, David J.</creator><general>John Wiley & Sons, Ltd</general><scope>BSCLL</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>200806</creationdate><title>Microwave-assisted Boc-solid phase peptide synthesis of cyclic cysteine-rich peptides</title><author>Čemažar, Maša ; Craik, David J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4502-65d9a601a66ea355b69824d59f60cabea0545b57e5f6aecc1f6ecdfb9219d9103</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Boc-SPPS</topic><topic>Chromatography, High Pressure Liquid</topic><topic>circular protein</topic><topic>Cysteine - chemistry</topic><topic>cystine knot</topic><topic>microwave</topic><topic>Microwaves</topic><topic>native chemical ligation</topic><topic>Peptides - chemical synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Čemažar, Maša</creatorcontrib><creatorcontrib>Craik, David J.</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of peptide science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Čemažar, Maša</au><au>Craik, David J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microwave-assisted Boc-solid phase peptide synthesis of cyclic cysteine-rich peptides</atitle><jtitle>Journal of peptide science</jtitle><addtitle>J. Peptide Sci</addtitle><date>2008-06</date><risdate>2008</risdate><volume>14</volume><issue>6</issue><spage>683</spage><epage>689</epage><pages>683-689</pages><issn>1075-2617</issn><eissn>1099-1387</eissn><abstract>In this study we describe the first protocols for the synthesis of cystine‐rich peptides in the presence of microwave radiation with Boc‐solid phase peptide synthesis (SPPS). This method is exemplified for macrocyclic peptides known as cyclotides, which comprise ∼30 amino acids and incorporate a cystine knot arrangement of their three disulfide bonds. However, the method is broadly applicable for a wide range of peptides using Boc‐SPPS, especially for SPPS of large peptides via native chemical ligation. Microwave radiation produces peptides in high yield and with high purity, and we were able to reduce the time for the assembly of ∼30 mer peptide chains to an overnight reaction in the automated microwave‐assisted synthesis. Copyright © 2007 European Peptide Society and John Wiley & Sons, Ltd.</abstract><cop>Chichester, UK</cop><pub>John Wiley & Sons, Ltd</pub><pmid>18044816</pmid><doi>10.1002/psc.972</doi><tpages>7</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 1075-2617
ispartof	Journal of peptide science, 2008-06, Vol.14 (6), p.683-689
issn	1075-2617 1099-1387
language	eng
recordid	cdi_proquest_miscellaneous_70759447
source	MEDLINE; Wiley Online Library Journals Frontfile Complete
subjects	Boc-SPPS Chromatography, High Pressure Liquid circular protein Cysteine - chemistry cystine knot microwave Microwaves native chemical ligation Peptides - chemical synthesis
title	Microwave-assisted Boc-solid phase peptide synthesis of cyclic cysteine-rich peptides
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-12T02%3A58%3A06IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Microwave-assisted%20Boc-solid%20phase%20peptide%20synthesis%20of%20cyclic%20cysteine-rich%20peptides&rft.jtitle=Journal%20of%20peptide%20science&rft.au=%C4%8Cema%C5%BEar,%20Ma%C5%A1a&rft.date=2008-06&rft.volume=14&rft.issue=6&rft.spage=683&rft.epage=689&rft.pages=683-689&rft.issn=1075-2617&rft.eissn=1099-1387&rft_id=info:doi/10.1002/psc.972&rft_dat=%3Cproquest_cross%3E21127826%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=21127826&rft_id=info:pmid/18044816&rfr_iscdi=true