Loading…
Sonogashira cross-coupling as a key step in the synthesis of new glycoporphyrins
Glycoporphyrins are an important subclass of the porphyrin family of compounds. They have been intensively studied because of their biological importance, i.e. they exhibit increased solubility in polar solvents and they might provide better selectivity towards biological targets. New methods for th...
Saved in:
| Published in: | Organic chemistry frontiers an international journal of organic chemistry 2022-05, Vol.9 (9), p.2396-2404 |
|---|---|
| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
| Subjects: | |
| Citations: | 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-c351t-a7144f0985d02f1e035cdd9d422e5ad7195372baba2e3d6853c6959909c97dbc3 |
|---|---|
| cites | |
| container_end_page | 2404 |
| container_issue | 9 |
| container_start_page | 2396 |
| container_title | Organic chemistry frontiers an international journal of organic chemistry |
| container_volume | 9 |
| creator | Godlewski, Bartosz Baran, Dariusz de Robichon, Morgane Ferry, Angélique Ostrowski, Stanisław Malinowski, Maciej |
| description | Glycoporphyrins are an important subclass of the porphyrin family of compounds. They have been intensively studied because of their biological importance, i.e. they exhibit increased solubility in polar solvents and they might provide better selectivity towards biological targets. New methods for the efficient synthesis of these compounds are highly desired. Unfortunately, in most of the described methodologies, carbohydrate-linked porphyrins are obtained through hydrolyzable connections. Herein, the original route to new C–C conjugated glycoporphyrins via the Sonogashira cross-coupling is presented. The optimal conditions have been established and the most convenient synthetic strategy has been determined. |
| doi_str_mv | 10.1039/d1qo01909k |
| format | article |
| fullrecord | <record><control><sourceid>proquest_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_03821224v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2658625230</sourcerecordid><originalsourceid>FETCH-LOGICAL-c351t-a7144f0985d02f1e035cdd9d422e5ad7195372baba2e3d6853c6959909c97dbc3</originalsourceid><addsrcrecordid>eNpNj8FLwzAYxYMoOOYu_gUBTx6qX740bXMcQ50wUFDPJUvSNVttuqRV-t9bmQdP7_H48XiPkGsGdwy4vDfs6IFJkIczMkMQmKSMwfk_f0kWMe4BgKHIQOQz8vrmW79TsXZBUR18jIn2Q9e4dkdVpIoe7EhjbzvqWtrXlsaxnSS6SH1FW_tNd82ofedDV4_BtfGKXFSqiXbxp3Py8fjwvlonm5en59Vyk2guWJ-onKVpBbIQBrBiFrjQxkiTIlqhTM6k4Dlu1Vah5SYrBNeZFHI6p2VutprPye2pt1ZN2QX3qcJYeuXK9XJT_mbAC2SI6Reb2JsT2wV_HGzsy70fQjvNKzETRYYCOfAfD39e_g</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2658625230</pqid></control><display><type>article</type><title>Sonogashira cross-coupling as a key step in the synthesis of new glycoporphyrins</title><source>Royal Society of Chemistry</source><creator>Godlewski, Bartosz ; Baran, Dariusz ; de Robichon, Morgane ; Ferry, Angélique ; Ostrowski, Stanisław ; Malinowski, Maciej</creator><creatorcontrib>Godlewski, Bartosz ; Baran, Dariusz ; de Robichon, Morgane ; Ferry, Angélique ; Ostrowski, Stanisław ; Malinowski, Maciej</creatorcontrib><description>Glycoporphyrins are an important subclass of the porphyrin family of compounds. They have been intensively studied because of their biological importance, i.e. they exhibit increased solubility in polar solvents and they might provide better selectivity towards biological targets. New methods for the efficient synthesis of these compounds are highly desired. Unfortunately, in most of the described methodologies, carbohydrate-linked porphyrins are obtained through hydrolyzable connections. Herein, the original route to new C–C conjugated glycoporphyrins via the Sonogashira cross-coupling is presented. The optimal conditions have been established and the most convenient synthetic strategy has been determined.</description><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/d1qo01909k</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Carbohydrates ; Chemical Sciences ; Cross coupling ; Organic chemistry ; Porphyrins ; Selectivity ; Synthesis</subject><ispartof>Organic chemistry frontiers an international journal of organic chemistry, 2022-05, Vol.9 (9), p.2396-2404</ispartof><rights>Copyright Royal Society of Chemistry 2022</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-c351t-a7144f0985d02f1e035cdd9d422e5ad7195372baba2e3d6853c6959909c97dbc3</citedby><orcidid>0000-0002-4586-8482</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27924,27925</link.rule.ids><backlink>$$Uhttps://hal.science/hal-03821224$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Godlewski, Bartosz</creatorcontrib><creatorcontrib>Baran, Dariusz</creatorcontrib><creatorcontrib>de Robichon, Morgane</creatorcontrib><creatorcontrib>Ferry, Angélique</creatorcontrib><creatorcontrib>Ostrowski, Stanisław</creatorcontrib><creatorcontrib>Malinowski, Maciej</creatorcontrib><title>Sonogashira cross-coupling as a key step in the synthesis of new glycoporphyrins</title><title>Organic chemistry frontiers an international journal of organic chemistry</title><description>Glycoporphyrins are an important subclass of the porphyrin family of compounds. They have been intensively studied because of their biological importance, i.e. they exhibit increased solubility in polar solvents and they might provide better selectivity towards biological targets. New methods for the efficient synthesis of these compounds are highly desired. Unfortunately, in most of the described methodologies, carbohydrate-linked porphyrins are obtained through hydrolyzable connections. Herein, the original route to new C–C conjugated glycoporphyrins via the Sonogashira cross-coupling is presented. The optimal conditions have been established and the most convenient synthetic strategy has been determined.</description><subject>Carbohydrates</subject><subject>Chemical Sciences</subject><subject>Cross coupling</subject><subject>Organic chemistry</subject><subject>Porphyrins</subject><subject>Selectivity</subject><subject>Synthesis</subject><issn>2052-4110</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpNj8FLwzAYxYMoOOYu_gUBTx6qX740bXMcQ50wUFDPJUvSNVttuqRV-t9bmQdP7_H48XiPkGsGdwy4vDfs6IFJkIczMkMQmKSMwfk_f0kWMe4BgKHIQOQz8vrmW79TsXZBUR18jIn2Q9e4dkdVpIoe7EhjbzvqWtrXlsaxnSS6SH1FW_tNd82ofedDV4_BtfGKXFSqiXbxp3Py8fjwvlonm5en59Vyk2guWJ-onKVpBbIQBrBiFrjQxkiTIlqhTM6k4Dlu1Vah5SYrBNeZFHI6p2VutprPye2pt1ZN2QX3qcJYeuXK9XJT_mbAC2SI6Reb2JsT2wV_HGzsy70fQjvNKzETRYYCOfAfD39e_g</recordid><startdate>20220503</startdate><enddate>20220503</enddate><creator>Godlewski, Bartosz</creator><creator>Baran, Dariusz</creator><creator>de Robichon, Morgane</creator><creator>Ferry, Angélique</creator><creator>Ostrowski, Stanisław</creator><creator>Malinowski, Maciej</creator><general>Royal Society of Chemistry</general><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-4586-8482</orcidid></search><sort><creationdate>20220503</creationdate><title>Sonogashira cross-coupling as a key step in the synthesis of new glycoporphyrins</title><author>Godlewski, Bartosz ; Baran, Dariusz ; de Robichon, Morgane ; Ferry, Angélique ; Ostrowski, Stanisław ; Malinowski, Maciej</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c351t-a7144f0985d02f1e035cdd9d422e5ad7195372baba2e3d6853c6959909c97dbc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Carbohydrates</topic><topic>Chemical Sciences</topic><topic>Cross coupling</topic><topic>Organic chemistry</topic><topic>Porphyrins</topic><topic>Selectivity</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Godlewski, Bartosz</creatorcontrib><creatorcontrib>Baran, Dariusz</creatorcontrib><creatorcontrib>de Robichon, Morgane</creatorcontrib><creatorcontrib>Ferry, Angélique</creatorcontrib><creatorcontrib>Ostrowski, Stanisław</creatorcontrib><creatorcontrib>Malinowski, Maciej</creatorcontrib><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Organic chemistry frontiers an international journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Godlewski, Bartosz</au><au>Baran, Dariusz</au><au>de Robichon, Morgane</au><au>Ferry, Angélique</au><au>Ostrowski, Stanisław</au><au>Malinowski, Maciej</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sonogashira cross-coupling as a key step in the synthesis of new glycoporphyrins</atitle><jtitle>Organic chemistry frontiers an international journal of organic chemistry</jtitle><date>2022-05-03</date><risdate>2022</risdate><volume>9</volume><issue>9</issue><spage>2396</spage><epage>2404</epage><pages>2396-2404</pages><issn>2052-4110</issn><eissn>2052-4110</eissn><abstract>Glycoporphyrins are an important subclass of the porphyrin family of compounds. They have been intensively studied because of their biological importance, i.e. they exhibit increased solubility in polar solvents and they might provide better selectivity towards biological targets. New methods for the efficient synthesis of these compounds are highly desired. Unfortunately, in most of the described methodologies, carbohydrate-linked porphyrins are obtained through hydrolyzable connections. Herein, the original route to new C–C conjugated glycoporphyrins via the Sonogashira cross-coupling is presented. The optimal conditions have been established and the most convenient synthetic strategy has been determined.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d1qo01909k</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-4586-8482</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2052-4110 |
| ispartof | Organic chemistry frontiers an international journal of organic chemistry, 2022-05, Vol.9 (9), p.2396-2404 |
| issn | 2052-4110 2052-4110 |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_hal_03821224v1 |
| source | Royal Society of Chemistry |
| subjects | Carbohydrates Chemical Sciences Cross coupling Organic chemistry Porphyrins Selectivity Synthesis |
| title | Sonogashira cross-coupling as a key step in the synthesis of new glycoporphyrins |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-02T15%3A43%3A14IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Sonogashira%20cross-coupling%20as%20a%20key%20step%20in%20the%20synthesis%20of%20new%20glycoporphyrins&rft.jtitle=Organic%20chemistry%20frontiers%20an%20international%20journal%20of%20organic%20chemistry&rft.au=Godlewski,%20Bartosz&rft.date=2022-05-03&rft.volume=9&rft.issue=9&rft.spage=2396&rft.epage=2404&rft.pages=2396-2404&rft.issn=2052-4110&rft.eissn=2052-4110&rft_id=info:doi/10.1039/d1qo01909k&rft_dat=%3Cproquest_hal_p%3E2658625230%3C/proquest_hal_p%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c351t-a7144f0985d02f1e035cdd9d422e5ad7195372baba2e3d6853c6959909c97dbc3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2658625230&rft_id=info:pmid/&rfr_iscdi=true |