Sporolides (original) (raw)
Sporolides A and B are polycyclic macrolides extracted from the obligate marine bacterium Salinispora tropica, which is found in ocean sediment. They are composed of a chlorinated cyclopenta[a]indene ring and a cyclohexenone moiety. They were the second group of compounds (after salinosporamide A) isolated from Salinispora, and were said to indicate the potential of marine actinomycetes as a source of novel secondary metabolites. The structures and absolute stereochemistries of both metabolites were elucidated using a combination of NMR spectroscopy and X-ray crystallography.
| Property | Value |
|---|---|
| dbo:abstract | Sporolides A and B are polycyclic macrolides extracted from the obligate marine bacterium Salinispora tropica, which is found in ocean sediment. They are composed of a chlorinated cyclopenta[a]indene ring and a cyclohexenone moiety. They were the second group of compounds (after salinosporamide A) isolated from Salinispora, and were said to indicate the potential of marine actinomycetes as a source of novel secondary metabolites. The structures and absolute stereochemistries of both metabolites were elucidated using a combination of NMR spectroscopy and X-ray crystallography. The complex aromatic structure of the sporolides was hypothesized to be derived from an unstable nine-membered ring enediyne precursor, which could undergo Bergman cyclization to generate a para-benzyne intermediate. Nucleophilic attack by chloride would account for the 1:1 mixture of sporolide A and B and for the single chlorine in these enediyne-derived natural products. This proposed mechanism was demonstrated in laboratory experiments, (en) |
| dbo:iupacName | (3S,7S,8R,12R,17R,19R,21R,25R)-23-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,26-tetraoxaheptacyclo[11.8.2.27,7.14,18.01,18.016,22.03,25]hexacosa-4,13(23),14,16(22)-tetraene-6,9-dione (en) |
| dbo:thumbnail | wiki-commons:Special:FilePath/Sporolides_A_and_B.jpg?width=300 |
| dbo:wikiPageID | 23556775 (xsd:integer) |
| dbo:wikiPageLength | 5809 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID | 1033919376 (xsd:integer) |
| dbo:wikiPageWikiLink | dbr:Enediyne dbr:Bergman_cyclization dbr:Macrolides dbr:O-quinone dbc:Cyclohexenes dbc:Epoxides dbc:Heterocyclic_compounds_with_7_or_more_rings dbc:Oxygen_heterocycles dbr:Salinosporamide_A dbr:Salinispora dbr:Total_synthesis dbr:Dynemicin_A dbc:Macrolides dbr:K._C._Nicolaou dbr:Metabolites dbr:Olefin dbr:Salinispora_tropica dbr:Ocean_sediment dbr:Para-benzyne dbr:Marine_bacterium dbr:File:Biosynthesis.jpg dbr:File:Nuc.jpg dbr:File:Synthesis.jpg |
| dbp:imagefile | Sporolides A and B.jpg (en) |
| dbp:iupacname | -23 (xsd:integer) |
| dbp:wikiPageUsesTemplate | dbt:Chembox dbt:Chembox_Identifiers dbt:Chembox_Properties dbt:Reflist |
| dcterms:subject | dbc:Cyclohexenes dbc:Epoxides dbc:Heterocyclic_compounds_with_7_or_more_rings dbc:Oxygen_heterocycles dbc:Macrolides |
| gold:hypernym | dbr:Macrolides |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q11173 dbo:ChemicalCompound |
| rdfs:comment | Sporolides A and B are polycyclic macrolides extracted from the obligate marine bacterium Salinispora tropica, which is found in ocean sediment. They are composed of a chlorinated cyclopenta[a]indene ring and a cyclohexenone moiety. They were the second group of compounds (after salinosporamide A) isolated from Salinispora, and were said to indicate the potential of marine actinomycetes as a source of novel secondary metabolites. The structures and absolute stereochemistries of both metabolites were elucidated using a combination of NMR spectroscopy and X-ray crystallography. (en) |
| rdfs:label | Sporolides (en) |
| owl:sameAs | freebase:Sporolides wikidata:Sporolides https://global.dbpedia.org/id/4w4pV |
| prov:wasDerivedFrom | wikipedia-en:Sporolides?oldid=1033919376&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/Biosynthesis.jpg wiki-commons:Special:FilePath/Nuc.jpg wiki-commons:Special:FilePath/Sporolides_A_and_B.jpg wiki-commons:Special:FilePath/Synthesis.jpg |
| foaf:isPrimaryTopicOf | wikipedia-en:Sporolides |
| is dbo:wikiPageWikiLink of | dbr:Bergman_cyclization dbr:K._C._Nicolaou dbr:Kedarcidin dbr:Salinispora_tropica |
| is foaf:primaryTopic of | wikipedia-en:Sporolides |
