Epimerization-Free Preparation of C‑Terminal Cys Peptide Acid by Fmoc SPPS Using Pseudoproline-Type Protecting Group

Epimerization-Free Preparation of C‑Terminal Cys Peptide Acid by Fmoc SPPS Using Pseudoproline-Type Protecting Group

Preparation of C-terminal Cys-containing peptide acid by Fmoc solid-phase peptide synthesis (SPPS) is difficult due to base-mediated epimerization at Cys. In this paper, use of a C-terminal pseudoproline structure and Trt­(2-Cl) resin achieved epimerization-free direct preparation of the C-terminal...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2020-02, Vol.85 (3), p.1674-1679
Hauptverfasser: Tsuda, Shugo, Masuda, Shun, Yoshiya, Taku
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1679
container_issue 3
container_start_page 1674
container_title Journal of organic chemistry
container_volume 85
creator Tsuda, Shugo
Masuda, Shun
Yoshiya, Taku
description Preparation of C-terminal Cys-containing peptide acid by Fmoc solid-phase peptide synthesis (SPPS) is difficult due to base-mediated epimerization at Cys. In this paper, use of a C-terminal pseudoproline structure and Trt­(2-Cl) resin achieved epimerization-free direct preparation of the C-terminal Cys-containing peptide acid by Fmoc SPPS. Additionally, the C-terminal Cys­(ΨDmp,Hpro)-containing protected peptide segment was applied to an epimerization-free segment condensation reaction.
doi_str_mv 10.1021/acs.joc.9b02344
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2307393772</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2307393772</sourcerecordid><originalsourceid>FETCH-LOGICAL-a333t-b32308174c3097a5f464eeda0407090985951b314c85e5e03801221a848f2b0e3</originalsourceid><addsrcrecordid>eNp1kMtq3DAUQEVoSSaPdXdFy0Lw5OrlxzIMmSQQqCGTtZHl66BgW65kF6ar_kJ-MV8STWbSXYVAIJ17EIeQbwyWDDi70iYsX5xZFjVwIeURWTDFIUkLkF_IAoDzRPBUnJDTEF4gLqXUMTkRLI07lQvy-2a0PXr7R0_WDcnaI9LS46j9xwV1LV29_X3doO_toDu62gZa4jjZBum1sQ2tt3TdO0Mfy_KRPgU7PNMy4Ny40bvODphstuNO6SY00-711rt5PCdfW90FvDicZ-RpfbNZ3SUPP2_vV9cPiRZCTEktuICcZdIIKDKtWplKxEaDhAwKKHJVKFYLJk2uUCGIHBjnTOcyb3kNKM7Ij703_ubXjGGqehsMdp0e0M2hivpMFCLLeESv9qjxLgSPbTV622u_rRhUu9hVjF3F2NUhdpz4fpDPdY_NP_6zbgQu98B-cvaxYPiv7h2PUYoS</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2307393772</pqid></control><display><type>article</type><title>Epimerization-Free Preparation of C‑Terminal Cys Peptide Acid by Fmoc SPPS Using Pseudoproline-Type Protecting Group</title><source>ACS Publications</source><creator>Tsuda, Shugo ; Masuda, Shun ; Yoshiya, Taku</creator><creatorcontrib>Tsuda, Shugo ; Masuda, Shun ; Yoshiya, Taku</creatorcontrib><description>Preparation of C-terminal Cys-containing peptide acid by Fmoc solid-phase peptide synthesis (SPPS) is difficult due to base-mediated epimerization at Cys. In this paper, use of a C-terminal pseudoproline structure and Trt­(2-Cl) resin achieved epimerization-free direct preparation of the C-terminal Cys-containing peptide acid by Fmoc SPPS. Additionally, the C-terminal Cys­(ΨDmp,Hpro)-containing protected peptide segment was applied to an epimerization-free segment condensation reaction.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.9b02344</identifier><identifier>PMID: 31631664</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2020-02, Vol.85 (3), p.1674-1679</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-b32308174c3097a5f464eeda0407090985951b314c85e5e03801221a848f2b0e3</citedby><cites>FETCH-LOGICAL-a333t-b32308174c3097a5f464eeda0407090985951b314c85e5e03801221a848f2b0e3</cites><orcidid>0000-0002-7276-5614</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.9b02344$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.9b02344$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31631664$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tsuda, Shugo</creatorcontrib><creatorcontrib>Masuda, Shun</creatorcontrib><creatorcontrib>Yoshiya, Taku</creatorcontrib><title>Epimerization-Free Preparation of C‑Terminal Cys Peptide Acid by Fmoc SPPS Using Pseudoproline-Type Protecting Group</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Preparation of C-terminal Cys-containing peptide acid by Fmoc solid-phase peptide synthesis (SPPS) is difficult due to base-mediated epimerization at Cys. In this paper, use of a C-terminal pseudoproline structure and Trt­(2-Cl) resin achieved epimerization-free direct preparation of the C-terminal Cys-containing peptide acid by Fmoc SPPS. Additionally, the C-terminal Cys­(ΨDmp,Hpro)-containing protected peptide segment was applied to an epimerization-free segment condensation reaction.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp1kMtq3DAUQEVoSSaPdXdFy0Lw5OrlxzIMmSQQqCGTtZHl66BgW65kF6ar_kJ-MV8STWbSXYVAIJ17EIeQbwyWDDi70iYsX5xZFjVwIeURWTDFIUkLkF_IAoDzRPBUnJDTEF4gLqXUMTkRLI07lQvy-2a0PXr7R0_WDcnaI9LS46j9xwV1LV29_X3doO_toDu62gZa4jjZBum1sQ2tt3TdO0Mfy_KRPgU7PNMy4Ny40bvODphstuNO6SY00-711rt5PCdfW90FvDicZ-RpfbNZ3SUPP2_vV9cPiRZCTEktuICcZdIIKDKtWplKxEaDhAwKKHJVKFYLJk2uUCGIHBjnTOcyb3kNKM7Ij703_ubXjGGqehsMdp0e0M2hivpMFCLLeESv9qjxLgSPbTV622u_rRhUu9hVjF3F2NUhdpz4fpDPdY_NP_6zbgQu98B-cvaxYPiv7h2PUYoS</recordid><startdate>20200207</startdate><enddate>20200207</enddate><creator>Tsuda, Shugo</creator><creator>Masuda, Shun</creator><creator>Yoshiya, Taku</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7276-5614</orcidid></search><sort><creationdate>20200207</creationdate><title>Epimerization-Free Preparation of C‑Terminal Cys Peptide Acid by Fmoc SPPS Using Pseudoproline-Type Protecting Group</title><author>Tsuda, Shugo ; Masuda, Shun ; Yoshiya, Taku</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-b32308174c3097a5f464eeda0407090985951b314c85e5e03801221a848f2b0e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tsuda, Shugo</creatorcontrib><creatorcontrib>Masuda, Shun</creatorcontrib><creatorcontrib>Yoshiya, Taku</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tsuda, Shugo</au><au>Masuda, Shun</au><au>Yoshiya, Taku</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Epimerization-Free Preparation of C‑Terminal Cys Peptide Acid by Fmoc SPPS Using Pseudoproline-Type Protecting Group</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2020-02-07</date><risdate>2020</risdate><volume>85</volume><issue>3</issue><spage>1674</spage><epage>1679</epage><pages>1674-1679</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Preparation of C-terminal Cys-containing peptide acid by Fmoc solid-phase peptide synthesis (SPPS) is difficult due to base-mediated epimerization at Cys. In this paper, use of a C-terminal pseudoproline structure and Trt­(2-Cl) resin achieved epimerization-free direct preparation of the C-terminal Cys-containing peptide acid by Fmoc SPPS. Additionally, the C-terminal Cys­(ΨDmp,Hpro)-containing protected peptide segment was applied to an epimerization-free segment condensation reaction.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>31631664</pmid><doi>10.1021/acs.joc.9b02344</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-7276-5614</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2020-02, Vol.85 (3), p.1674-1679
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_2307393772
source ACS Publications
title Epimerization-Free Preparation of C‑Terminal Cys Peptide Acid by Fmoc SPPS Using Pseudoproline-Type Protecting Group
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-06T11%3A33%3A05IST&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=Epimerization-Free%20Preparation%20of%20C%E2%80%91Terminal%20Cys%20Peptide%20Acid%20by%20Fmoc%20SPPS%20Using%20Pseudoproline-Type%20Protecting%20Group&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Tsuda,%20Shugo&rft.date=2020-02-07&rft.volume=85&rft.issue=3&rft.spage=1674&rft.epage=1679&rft.pages=1674-1679&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.9b02344&rft_dat=%3Cproquest_cross%3E2307393772%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=2307393772&rft_id=info:pmid/31631664&rfr_iscdi=true