Membrane Receptor Probes:  Solid-Phase Synthesis of Biotin-Asp-PEG-arvanil Derivatives

A modular, flexible solid-phase synthetic route for the preparation of biotinylated cross-linking probes of membrane receptors is described. The route utilizes an orthogonal protection strategy employing a Pd[0] cleavable allyl linker attached to the probe via an aspartate residue. The versatility o...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2005-04, Vol.7 (9), p.1699-1702
Main Authors: Visintin, Cristina, Aliev, Abil E, Riddall, Dieter, Baker, David, Okuyama, Masahiro, Hoi, Pui Man, Hiley, Robin, Selwood, David L
Format: Article
Language:English
Subjects:
Aspartic Acid - analogs & derivatives
Aspartic Acid - chemical synthesis
Biotin - chemical synthesis
Biotinylation
Capsaicin - analogs & derivatives
Capsaicin - chemical synthesis
Cross-Linking Reagents - chemical synthesis
Molecular Probes - chemical synthesis
Molecular Structure
Photoaffinity Labels - chemical synthesis
Receptors, Cannabinoid - metabolism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a313t-6734e7ed61eccdd26f7400b62c87bc0dfd7404d813c6c2b967fa3558a3b4425b3
cites cdi_FETCH-LOGICAL-a313t-6734e7ed61eccdd26f7400b62c87bc0dfd7404d813c6c2b967fa3558a3b4425b3
container_end_page 1702
container_issue 9
container_start_page 1699
container_title Organic letters
container_volume 7
creator Visintin, Cristina
Aliev, Abil E
Riddall, Dieter
Baker, David
Okuyama, Masahiro
Hoi, Pui Man
Hiley, Robin
Selwood, David L
description A modular, flexible solid-phase synthetic route for the preparation of biotinylated cross-linking probes of membrane receptors is described. The route utilizes an orthogonal protection strategy employing a Pd[0] cleavable allyl linker attached to the probe via an aspartate residue. The versatility of the method is illustrated through the synthesis of a number of arvanil-derived cannabinoid receptor ligands displaying either a photoaffinity or a chemical cross-linking group.
doi_str_mv 10.1021/ol0502578
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_67768366</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>67768366</sourcerecordid><originalsourceid>FETCH-LOGICAL-a313t-6734e7ed61eccdd26f7400b62c87bc0dfd7404d813c6c2b967fa3558a3b4425b3</originalsourceid><addsrcrecordid>eNptkE9LwzAYh4Mobk4PfgHpRcFDNGnaJPM255zCxOEUvJU0fcsy2mYm7WA3r35NP4mVjXnx9P7h4Qe_B6FTSq4oCem1LUhMwljIPdSlcciwIHG4v9s56aAj7xeE0PbTP0QdGssokjLqovcnKFOnKgheQMOyti6YOpuCv_n-_ApmtjAZns6Vh2C2ruo5eOMDmwe3xtamwgO_xNPRGCu3UpUpgjtwZqVqswJ_jA5yVXg42c4eersfvQ4f8OR5_DgcTLBilNWYCxaBgIxT0DrLQp6LiJCUh1qKVJMsz9o7yiRlmusw7XORKxbHUrE0isI4ZT10scldOvvRgK-T0ngNRdF2so1PuBBcMs5b8HIDame9d5AnS2dK5dYJJcmvxmSnsWXPtqFNWkL2R269tcD5BlDaJwvbuKrt-E_QDzvbeTc</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>67768366</pqid></control><display><type>article</type><title>Membrane Receptor Probes:  Solid-Phase Synthesis of Biotin-Asp-PEG-arvanil Derivatives</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Visintin, Cristina ; Aliev, Abil E ; Riddall, Dieter ; Baker, David ; Okuyama, Masahiro ; Hoi, Pui Man ; Hiley, Robin ; Selwood, David L</creator><creatorcontrib>Visintin, Cristina ; Aliev, Abil E ; Riddall, Dieter ; Baker, David ; Okuyama, Masahiro ; Hoi, Pui Man ; Hiley, Robin ; Selwood, David L</creatorcontrib><description>A modular, flexible solid-phase synthetic route for the preparation of biotinylated cross-linking probes of membrane receptors is described. The route utilizes an orthogonal protection strategy employing a Pd[0] cleavable allyl linker attached to the probe via an aspartate residue. The versatility of the method is illustrated through the synthesis of a number of arvanil-derived cannabinoid receptor ligands displaying either a photoaffinity or a chemical cross-linking group.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol0502578</identifier><identifier>PMID: 15844884</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Aspartic Acid - analogs &amp; derivatives ; Aspartic Acid - chemical synthesis ; Biotin - chemical synthesis ; Biotinylation ; Capsaicin - analogs &amp; derivatives ; Capsaicin - chemical synthesis ; Cross-Linking Reagents - chemical synthesis ; Molecular Probes - chemical synthesis ; Molecular Structure ; Photoaffinity Labels - chemical synthesis ; Receptors, Cannabinoid - metabolism</subject><ispartof>Organic letters, 2005-04, Vol.7 (9), p.1699-1702</ispartof><rights>Copyright © 2005 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a313t-6734e7ed61eccdd26f7400b62c87bc0dfd7404d813c6c2b967fa3558a3b4425b3</citedby><cites>FETCH-LOGICAL-a313t-6734e7ed61eccdd26f7400b62c87bc0dfd7404d813c6c2b967fa3558a3b4425b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15844884$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Visintin, Cristina</creatorcontrib><creatorcontrib>Aliev, Abil E</creatorcontrib><creatorcontrib>Riddall, Dieter</creatorcontrib><creatorcontrib>Baker, David</creatorcontrib><creatorcontrib>Okuyama, Masahiro</creatorcontrib><creatorcontrib>Hoi, Pui Man</creatorcontrib><creatorcontrib>Hiley, Robin</creatorcontrib><creatorcontrib>Selwood, David L</creatorcontrib><title>Membrane Receptor Probes:  Solid-Phase Synthesis of Biotin-Asp-PEG-arvanil Derivatives</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A modular, flexible solid-phase synthetic route for the preparation of biotinylated cross-linking probes of membrane receptors is described. The route utilizes an orthogonal protection strategy employing a Pd[0] cleavable allyl linker attached to the probe via an aspartate residue. The versatility of the method is illustrated through the synthesis of a number of arvanil-derived cannabinoid receptor ligands displaying either a photoaffinity or a chemical cross-linking group.</description><subject>Aspartic Acid - analogs &amp; derivatives</subject><subject>Aspartic Acid - chemical synthesis</subject><subject>Biotin - chemical synthesis</subject><subject>Biotinylation</subject><subject>Capsaicin - analogs &amp; derivatives</subject><subject>Capsaicin - chemical synthesis</subject><subject>Cross-Linking Reagents - chemical synthesis</subject><subject>Molecular Probes - chemical synthesis</subject><subject>Molecular Structure</subject><subject>Photoaffinity Labels - chemical synthesis</subject><subject>Receptors, Cannabinoid - metabolism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNptkE9LwzAYh4Mobk4PfgHpRcFDNGnaJPM255zCxOEUvJU0fcsy2mYm7WA3r35NP4mVjXnx9P7h4Qe_B6FTSq4oCem1LUhMwljIPdSlcciwIHG4v9s56aAj7xeE0PbTP0QdGssokjLqovcnKFOnKgheQMOyti6YOpuCv_n-_ApmtjAZns6Vh2C2ruo5eOMDmwe3xtamwgO_xNPRGCu3UpUpgjtwZqVqswJ_jA5yVXg42c4eersfvQ4f8OR5_DgcTLBilNWYCxaBgIxT0DrLQp6LiJCUh1qKVJMsz9o7yiRlmusw7XORKxbHUrE0isI4ZT10scldOvvRgK-T0ngNRdF2so1PuBBcMs5b8HIDame9d5AnS2dK5dYJJcmvxmSnsWXPtqFNWkL2R269tcD5BlDaJwvbuKrt-E_QDzvbeTc</recordid><startdate>20050428</startdate><enddate>20050428</enddate><creator>Visintin, Cristina</creator><creator>Aliev, Abil E</creator><creator>Riddall, Dieter</creator><creator>Baker, David</creator><creator>Okuyama, Masahiro</creator><creator>Hoi, Pui Man</creator><creator>Hiley, Robin</creator><creator>Selwood, David L</creator><general>American Chemical Society</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>20050428</creationdate><title>Membrane Receptor Probes:  Solid-Phase Synthesis of Biotin-Asp-PEG-arvanil Derivatives</title><author>Visintin, Cristina ; Aliev, Abil E ; Riddall, Dieter ; Baker, David ; Okuyama, Masahiro ; Hoi, Pui Man ; Hiley, Robin ; Selwood, David L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a313t-6734e7ed61eccdd26f7400b62c87bc0dfd7404d813c6c2b967fa3558a3b4425b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Aspartic Acid - analogs &amp; derivatives</topic><topic>Aspartic Acid - chemical synthesis</topic><topic>Biotin - chemical synthesis</topic><topic>Biotinylation</topic><topic>Capsaicin - analogs &amp; derivatives</topic><topic>Capsaicin - chemical synthesis</topic><topic>Cross-Linking Reagents - chemical synthesis</topic><topic>Molecular Probes - chemical synthesis</topic><topic>Molecular Structure</topic><topic>Photoaffinity Labels - chemical synthesis</topic><topic>Receptors, Cannabinoid - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Visintin, Cristina</creatorcontrib><creatorcontrib>Aliev, Abil E</creatorcontrib><creatorcontrib>Riddall, Dieter</creatorcontrib><creatorcontrib>Baker, David</creatorcontrib><creatorcontrib>Okuyama, Masahiro</creatorcontrib><creatorcontrib>Hoi, Pui Man</creatorcontrib><creatorcontrib>Hiley, Robin</creatorcontrib><creatorcontrib>Selwood, David L</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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Visintin, Cristina</au><au>Aliev, Abil E</au><au>Riddall, Dieter</au><au>Baker, David</au><au>Okuyama, Masahiro</au><au>Hoi, Pui Man</au><au>Hiley, Robin</au><au>Selwood, David L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Membrane Receptor Probes:  Solid-Phase Synthesis of Biotin-Asp-PEG-arvanil Derivatives</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2005-04-28</date><risdate>2005</risdate><volume>7</volume><issue>9</issue><spage>1699</spage><epage>1702</epage><pages>1699-1702</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A modular, flexible solid-phase synthetic route for the preparation of biotinylated cross-linking probes of membrane receptors is described. The route utilizes an orthogonal protection strategy employing a Pd[0] cleavable allyl linker attached to the probe via an aspartate residue. The versatility of the method is illustrated through the synthesis of a number of arvanil-derived cannabinoid receptor ligands displaying either a photoaffinity or a chemical cross-linking group.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>15844884</pmid><doi>10.1021/ol0502578</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2005-04, Vol.7 (9), p.1699-1702
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_67768366
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Aspartic Acid - analogs & derivatives
Aspartic Acid - chemical synthesis
Biotin - chemical synthesis
Biotinylation
Capsaicin - analogs & derivatives
Capsaicin - chemical synthesis
Cross-Linking Reagents - chemical synthesis
Molecular Probes - chemical synthesis
Molecular Structure
Photoaffinity Labels - chemical synthesis
Receptors, Cannabinoid - metabolism
title Membrane Receptor Probes:  Solid-Phase Synthesis of Biotin-Asp-PEG-arvanil Derivatives
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-19T21%3A09%3A44IST&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=Membrane%20Receptor%20Probes:%E2%80%89%20Solid-Phase%20Synthesis%20of%20Biotin-Asp-PEG-arvanil%20Derivatives&rft.jtitle=Organic%20letters&rft.au=Visintin,%20Cristina&rft.date=2005-04-28&rft.volume=7&rft.issue=9&rft.spage=1699&rft.epage=1702&rft.pages=1699-1702&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol0502578&rft_dat=%3Cproquest_cross%3E67768366%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a313t-6734e7ed61eccdd26f7400b62c87bc0dfd7404d813c6c2b967fa3558a3b4425b3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=67768366&rft_id=info:pmid/15844884&rfr_iscdi=true