Design and Synthesis of Nucleoproline Amino Acids for the Straightforward Preparation of Chiral and Conformationally Constrained Nucleopeptides

A straightforward synthesis of orthogonally protected nucleoproline (Nup) amino acids and their coupling to oligomers are described. A key step is the attachment of alkynylated nucleobases to Fmoc‐protected 4‐azidoproline (Fmoc‐Azp‐OH) by a Cu‐catalyzed 1,3‐dipolar cycloaddition (‘click reaction’)....

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Helvetica chimica acta 2012-12, Vol.95 (12), p.2621-2634
Hauptverfasser:	Kramer, Rolf A., Bleicher, Konrad H., Wennemers, Helma
Format:	Artikel
Sprache:	eng
Schlagworte:	Amino acids Catalysis Click chemistry Copper catalysis Cycloadditions Nucleopeptides Peptides Proline derivatives
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	2634
container_issue	12
container_start_page	2621
container_title	Helvetica chimica acta
container_volume	95
creator	Kramer, Rolf A. Bleicher, Konrad H. Wennemers, Helma
description	A straightforward synthesis of orthogonally protected nucleoproline (Nup) amino acids and their coupling to oligomers are described. A key step is the attachment of alkynylated nucleobases to Fmoc‐protected 4‐azidoproline (Fmoc‐Azp‐OH) by a Cu‐catalyzed 1,3‐dipolar cycloaddition (‘click reaction’). The developed protocol allows preparation of the nucleoprolines in scales of >30 g. Solid‐phase peptide synthesis proved to be straightforward with these Nup amino acids. The resulting oligonucleoproline peptides adopt defined helices, are very well H2O soluble, and show comparable cell‐penetrating properties as recently reported α‐nucleoalanine peptides.
doi_str_mv	10.1002/hlca.201200557
format	Article
fullrecord	<record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_1240094918</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2844867521</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3557-245f458835007848f306d04681887549ea0ea04c66514f10f4fb39e3b56301763</originalsourceid><addsrcrecordid>eNqFkF9PwyAUxYnRxPnn1WcSnzsvBVr6uFSdJosap3FvBFtwaFcmdNF9Cr-y1KnxzYSEXO75He49CB0RGBKA9GTeVGqYAkkBOM-30IDwNE3SLOfbaABARAKkmO2ivRCeAaAoIB-gj1Md7FOLVVvj6brt5rEM2Bl8taoa7ZbeNbbVeLSwrcOjytYBG-dx1OFp55V9mnexflO-xjdeL5VXnXVtb1DOrVfNl3Hp2ihafLVU06z7h9DTra5_PtLLztY6HKAdo5qgD7_vfXR_fnZXXiST6_FlOZokFY3LJSnjhnEhKAfIBROGQlYDywQRIues0AriYVWWccIMAcPMIy00feQZBZJndB8db3zjhq8rHTr57FY-ThckSVlMhxVERNVwo6q8C8FrI5feLpRfSwKyD132ocvf0CNQbIA32-j1P2p5MSlHf9lkw9rQ6fdfVvkXmeU05_Lhaixnt6ezaTGbygn9BAR7lpA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1240094918</pqid></control><display><type>article</type><title>Design and Synthesis of Nucleoproline Amino Acids for the Straightforward Preparation of Chiral and Conformationally Constrained Nucleopeptides</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Kramer, Rolf A. ; Bleicher, Konrad H. ; Wennemers, Helma</creator><creatorcontrib>Kramer, Rolf A. ; Bleicher, Konrad H. ; Wennemers, Helma</creatorcontrib><description>A straightforward synthesis of orthogonally protected nucleoproline (Nup) amino acids and their coupling to oligomers are described. A key step is the attachment of alkynylated nucleobases to Fmoc‐protected 4‐azidoproline (Fmoc‐Azp‐OH) by a Cu‐catalyzed 1,3‐dipolar cycloaddition (‘click reaction’). The developed protocol allows preparation of the nucleoprolines in scales of >30 g. Solid‐phase peptide synthesis proved to be straightforward with these Nup amino acids. The resulting oligonucleoproline peptides adopt defined helices, are very well H2O soluble, and show comparable cell‐penetrating properties as recently reported α‐nucleoalanine peptides.</description><identifier>ISSN: 0018-019X</identifier><identifier>EISSN: 1522-2675</identifier><identifier>DOI: 10.1002/hlca.201200557</identifier><language>eng</language><publisher>Zürich: WILEY-VCH Verlag</publisher><subject>Amino acids ; Catalysis ; Click chemistry ; Copper catalysis ; Cycloadditions ; Nucleopeptides ; Peptides ; Proline derivatives</subject><ispartof>Helvetica chimica acta, 2012-12, Vol.95 (12), p.2621-2634</ispartof><rights>Copyright © 2012 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3557-245f458835007848f306d04681887549ea0ea04c66514f10f4fb39e3b56301763</citedby><cites>FETCH-LOGICAL-c3557-245f458835007848f306d04681887549ea0ea04c66514f10f4fb39e3b56301763</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%2Fhlca.201200557$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fhlca.201200557$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Kramer, Rolf A.</creatorcontrib><creatorcontrib>Bleicher, Konrad H.</creatorcontrib><creatorcontrib>Wennemers, Helma</creatorcontrib><title>Design and Synthesis of Nucleoproline Amino Acids for the Straightforward Preparation of Chiral and Conformationally Constrained Nucleopeptides</title><title>Helvetica chimica acta</title><addtitle>HCA</addtitle><description>A straightforward synthesis of orthogonally protected nucleoproline (Nup) amino acids and their coupling to oligomers are described. A key step is the attachment of alkynylated nucleobases to Fmoc‐protected 4‐azidoproline (Fmoc‐Azp‐OH) by a Cu‐catalyzed 1,3‐dipolar cycloaddition (‘click reaction’). The developed protocol allows preparation of the nucleoprolines in scales of >30 g. Solid‐phase peptide synthesis proved to be straightforward with these Nup amino acids. The resulting oligonucleoproline peptides adopt defined helices, are very well H2O soluble, and show comparable cell‐penetrating properties as recently reported α‐nucleoalanine peptides.</description><subject>Amino acids</subject><subject>Catalysis</subject><subject>Click chemistry</subject><subject>Copper catalysis</subject><subject>Cycloadditions</subject><subject>Nucleopeptides</subject><subject>Peptides</subject><subject>Proline derivatives</subject><issn>0018-019X</issn><issn>1522-2675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqFkF9PwyAUxYnRxPnn1WcSnzsvBVr6uFSdJosap3FvBFtwaFcmdNF9Cr-y1KnxzYSEXO75He49CB0RGBKA9GTeVGqYAkkBOM-30IDwNE3SLOfbaABARAKkmO2ivRCeAaAoIB-gj1Md7FOLVVvj6brt5rEM2Bl8taoa7ZbeNbbVeLSwrcOjytYBG-dx1OFp55V9mnexflO-xjdeL5VXnXVtb1DOrVfNl3Hp2ihafLVU06z7h9DTra5_PtLLztY6HKAdo5qgD7_vfXR_fnZXXiST6_FlOZokFY3LJSnjhnEhKAfIBROGQlYDywQRIues0AriYVWWccIMAcPMIy00feQZBZJndB8db3zjhq8rHTr57FY-ThckSVlMhxVERNVwo6q8C8FrI5feLpRfSwKyD132ocvf0CNQbIA32-j1P2p5MSlHf9lkw9rQ6fdfVvkXmeU05_Lhaixnt6ezaTGbygn9BAR7lpA</recordid><startdate>201212</startdate><enddate>201212</enddate><creator>Kramer, Rolf A.</creator><creator>Bleicher, Konrad H.</creator><creator>Wennemers, Helma</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>7QO</scope><scope>7T7</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>M7N</scope><scope>P64</scope></search><sort><creationdate>201212</creationdate><title>Design and Synthesis of Nucleoproline Amino Acids for the Straightforward Preparation of Chiral and Conformationally Constrained Nucleopeptides</title><author>Kramer, Rolf A. ; Bleicher, Konrad H. ; Wennemers, Helma</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3557-245f458835007848f306d04681887549ea0ea04c66514f10f4fb39e3b56301763</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Amino acids</topic><topic>Catalysis</topic><topic>Click chemistry</topic><topic>Copper catalysis</topic><topic>Cycloadditions</topic><topic>Nucleopeptides</topic><topic>Peptides</topic><topic>Proline derivatives</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kramer, Rolf A.</creatorcontrib><creatorcontrib>Bleicher, Konrad H.</creatorcontrib><creatorcontrib>Wennemers, Helma</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Helvetica chimica acta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kramer, Rolf A.</au><au>Bleicher, Konrad H.</au><au>Wennemers, Helma</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design and Synthesis of Nucleoproline Amino Acids for the Straightforward Preparation of Chiral and Conformationally Constrained Nucleopeptides</atitle><jtitle>Helvetica chimica acta</jtitle><addtitle>HCA</addtitle><date>2012-12</date><risdate>2012</risdate><volume>95</volume><issue>12</issue><spage>2621</spage><epage>2634</epage><pages>2621-2634</pages><issn>0018-019X</issn><eissn>1522-2675</eissn><abstract>A straightforward synthesis of orthogonally protected nucleoproline (Nup) amino acids and their coupling to oligomers are described. A key step is the attachment of alkynylated nucleobases to Fmoc‐protected 4‐azidoproline (Fmoc‐Azp‐OH) by a Cu‐catalyzed 1,3‐dipolar cycloaddition (‘click reaction’). The developed protocol allows preparation of the nucleoprolines in scales of >30 g. Solid‐phase peptide synthesis proved to be straightforward with these Nup amino acids. The resulting oligonucleoproline peptides adopt defined helices, are very well H2O soluble, and show comparable cell‐penetrating properties as recently reported α‐nucleoalanine peptides.</abstract><cop>Zürich</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/hlca.201200557</doi><tpages>14</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 0018-019X
ispartof	Helvetica chimica acta, 2012-12, Vol.95 (12), p.2621-2634
issn	0018-019X 1522-2675
language	eng
recordid	cdi_proquest_journals_1240094918
source	Wiley Online Library Journals Frontfile Complete
subjects	Amino acids Catalysis Click chemistry Copper catalysis Cycloadditions Nucleopeptides Peptides Proline derivatives
title	Design and Synthesis of Nucleoproline Amino Acids for the Straightforward Preparation of Chiral and Conformationally Constrained Nucleopeptides
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-31T04%3A08%3A55IST&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=Design%20and%20Synthesis%20of%20Nucleoproline%20Amino%20Acids%20for%20the%20Straightforward%20Preparation%20of%20Chiral%20and%20Conformationally%20Constrained%20Nucleopeptides&rft.jtitle=Helvetica%20chimica%20acta&rft.au=Kramer,%20Rolf%20A.&rft.date=2012-12&rft.volume=95&rft.issue=12&rft.spage=2621&rft.epage=2634&rft.pages=2621-2634&rft.issn=0018-019X&rft.eissn=1522-2675&rft_id=info:doi/10.1002/hlca.201200557&rft_dat=%3Cproquest_cross%3E2844867521%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=1240094918&rft_id=info:pmid/&rfr_iscdi=true