Synthesis of the C50 diastereomers of the C33–C51 fragment of stambomycin D

As products of genome mining, the stereochemical assignment of the macrolide antibiotics stambomycins A–D has been made on the basis of sequence analysis of the associated polyketide synthase, aside from two stereocentres at C28 and C50. Here we describe syntheses of the two C50 diastereomers of the...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic Chemistry Frontiers 2022-01, Vol.9 (2), p.445-449
Hauptverfasser: Wang, Yongchen, Chintalapudi, Venkaiah, Gudmundsson, Haraldur G., Challis, Gregory L., Anderson, Edward A.
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 449
container_issue 2
container_start_page 445
container_title Organic Chemistry Frontiers
container_volume 9
creator Wang, Yongchen
Chintalapudi, Venkaiah
Gudmundsson, Haraldur G.
Challis, Gregory L.
Anderson, Edward A.
description As products of genome mining, the stereochemical assignment of the macrolide antibiotics stambomycins A–D has been made on the basis of sequence analysis of the associated polyketide synthase, aside from two stereocentres at C28 and C50. Here we describe syntheses of the two C50 diastereomers of the C33–C51 region of the stambomycins, which support the PKS-based configurational assignment, and establish a strategy suitable for access to the extended stambomycin framework.
doi_str_mv 10.1039/D1QO01635K
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2620299384</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2620299384</sourcerecordid><originalsourceid>FETCH-LOGICAL-c276t-e447e2fd8b653e6e8edc43422e746b6173bd1b71585594584a35bd0863eb91573</originalsourceid><addsrcrecordid>eNpNkM1Kw0AcxBdRsNRefIIFb0J0v_67yVFSv7BSRD0vu8k_mmKSupsecvMdfEOfxJQK9TQD82MGhpBTzi44k9nlnD8tGdcSHg7IRDAQieIiO_znj8ksxhVjjAvQDMyEPD4Pbf-OsY60q-joaA6MlrWLPQbsGgz7QMqfr-8cOK2Ce2uw7bdJ7F3ju2Yo6pbOT8hR5T4izv50Sl5vrl_yu2SxvL3PrxZJIYzuE1TKoKjK1GuQqDHFslBSCYFGaa-5kb7k3nBIATIFqXISfMlSLdFnHIyckrNd7zp0nxuMvV11m9COk1ZowUSWyVSN1PmOKkIXY8DKrkPduDBYzuz2Mbt_TP4CKNhbVg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2620299384</pqid></control><display><type>article</type><title>Synthesis of the C50 diastereomers of the C33–C51 fragment of stambomycin D</title><source>Royal Society Of Chemistry Journals 2008-</source><creator>Wang, Yongchen ; Chintalapudi, Venkaiah ; Gudmundsson, Haraldur G. ; Challis, Gregory L. ; Anderson, Edward A.</creator><creatorcontrib>Wang, Yongchen ; Chintalapudi, Venkaiah ; Gudmundsson, Haraldur G. ; Challis, Gregory L. ; Anderson, Edward A.</creatorcontrib><description>As products of genome mining, the stereochemical assignment of the macrolide antibiotics stambomycins A–D has been made on the basis of sequence analysis of the associated polyketide synthase, aside from two stereocentres at C28 and C50. Here we describe syntheses of the two C50 diastereomers of the C33–C51 region of the stambomycins, which support the PKS-based configurational assignment, and establish a strategy suitable for access to the extended stambomycin framework.</description><identifier>ISSN: 2052-4129</identifier><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4129</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/D1QO01635K</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Antibiotics ; Diastereoisomers ; Genomes ; Macrolide antibiotics ; Organic chemistry ; Polyketide synthase ; Sequence analysis</subject><ispartof>Organic Chemistry Frontiers, 2022-01, Vol.9 (2), p.445-449</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c276t-e447e2fd8b653e6e8edc43422e746b6173bd1b71585594584a35bd0863eb91573</cites><orcidid>0000-0002-4149-0494 ; 0000-0001-5976-3545</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Wang, Yongchen</creatorcontrib><creatorcontrib>Chintalapudi, Venkaiah</creatorcontrib><creatorcontrib>Gudmundsson, Haraldur G.</creatorcontrib><creatorcontrib>Challis, Gregory L.</creatorcontrib><creatorcontrib>Anderson, Edward A.</creatorcontrib><title>Synthesis of the C50 diastereomers of the C33–C51 fragment of stambomycin D</title><title>Organic Chemistry Frontiers</title><description>As products of genome mining, the stereochemical assignment of the macrolide antibiotics stambomycins A–D has been made on the basis of sequence analysis of the associated polyketide synthase, aside from two stereocentres at C28 and C50. Here we describe syntheses of the two C50 diastereomers of the C33–C51 region of the stambomycins, which support the PKS-based configurational assignment, and establish a strategy suitable for access to the extended stambomycin framework.</description><subject>Antibiotics</subject><subject>Diastereoisomers</subject><subject>Genomes</subject><subject>Macrolide antibiotics</subject><subject>Organic chemistry</subject><subject>Polyketide synthase</subject><subject>Sequence analysis</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpNkM1Kw0AcxBdRsNRefIIFb0J0v_67yVFSv7BSRD0vu8k_mmKSupsecvMdfEOfxJQK9TQD82MGhpBTzi44k9nlnD8tGdcSHg7IRDAQieIiO_znj8ksxhVjjAvQDMyEPD4Pbf-OsY60q-joaA6MlrWLPQbsGgz7QMqfr-8cOK2Ce2uw7bdJ7F3ju2Yo6pbOT8hR5T4izv50Sl5vrl_yu2SxvL3PrxZJIYzuE1TKoKjK1GuQqDHFslBSCYFGaa-5kb7k3nBIATIFqXISfMlSLdFnHIyckrNd7zp0nxuMvV11m9COk1ZowUSWyVSN1PmOKkIXY8DKrkPduDBYzuz2Mbt_TP4CKNhbVg</recordid><startdate>20220118</startdate><enddate>20220118</enddate><creator>Wang, Yongchen</creator><creator>Chintalapudi, Venkaiah</creator><creator>Gudmundsson, Haraldur G.</creator><creator>Challis, Gregory L.</creator><creator>Anderson, Edward A.</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0002-4149-0494</orcidid><orcidid>https://orcid.org/0000-0001-5976-3545</orcidid></search><sort><creationdate>20220118</creationdate><title>Synthesis of the C50 diastereomers of the C33–C51 fragment of stambomycin D</title><author>Wang, Yongchen ; Chintalapudi, Venkaiah ; Gudmundsson, Haraldur G. ; Challis, Gregory L. ; Anderson, Edward A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c276t-e447e2fd8b653e6e8edc43422e746b6173bd1b71585594584a35bd0863eb91573</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Antibiotics</topic><topic>Diastereoisomers</topic><topic>Genomes</topic><topic>Macrolide antibiotics</topic><topic>Organic chemistry</topic><topic>Polyketide synthase</topic><topic>Sequence analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Yongchen</creatorcontrib><creatorcontrib>Chintalapudi, Venkaiah</creatorcontrib><creatorcontrib>Gudmundsson, Haraldur G.</creatorcontrib><creatorcontrib>Challis, Gregory L.</creatorcontrib><creatorcontrib>Anderson, Edward A.</creatorcontrib><collection>CrossRef</collection><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><jtitle>Organic Chemistry Frontiers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Yongchen</au><au>Chintalapudi, Venkaiah</au><au>Gudmundsson, Haraldur G.</au><au>Challis, Gregory L.</au><au>Anderson, Edward A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of the C50 diastereomers of the C33–C51 fragment of stambomycin D</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2022-01-18</date><risdate>2022</risdate><volume>9</volume><issue>2</issue><spage>445</spage><epage>449</epage><pages>445-449</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>As products of genome mining, the stereochemical assignment of the macrolide antibiotics stambomycins A–D has been made on the basis of sequence analysis of the associated polyketide synthase, aside from two stereocentres at C28 and C50. Here we describe syntheses of the two C50 diastereomers of the C33–C51 region of the stambomycins, which support the PKS-based configurational assignment, and establish a strategy suitable for access to the extended stambomycin framework.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D1QO01635K</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-4149-0494</orcidid><orcidid>https://orcid.org/0000-0001-5976-3545</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 2052-4129
ispartof Organic Chemistry Frontiers, 2022-01, Vol.9 (2), p.445-449
issn 2052-4129
2052-4110
2052-4129
2052-4110
language eng
recordid cdi_proquest_journals_2620299384
source Royal Society Of Chemistry Journals 2008-
subjects Antibiotics
Diastereoisomers
Genomes
Macrolide antibiotics
Organic chemistry
Polyketide synthase
Sequence analysis
title Synthesis of the C50 diastereomers of the C33–C51 fragment of stambomycin D
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-10T04%3A42%3A54IST&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=Synthesis%20of%20the%20C50%20diastereomers%20of%20the%20C33%E2%80%93C51%20fragment%20of%20stambomycin%20D&rft.jtitle=Organic%20Chemistry%20Frontiers&rft.au=Wang,%20Yongchen&rft.date=2022-01-18&rft.volume=9&rft.issue=2&rft.spage=445&rft.epage=449&rft.pages=445-449&rft.issn=2052-4129&rft.eissn=2052-4129&rft_id=info:doi/10.1039/D1QO01635K&rft_dat=%3Cproquest_cross%3E2620299384%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=2620299384&rft_id=info:pmid/&rfr_iscdi=true