{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Economou C"],"funding":["Yale University","NCI NIH HHS","National Institutes of Health","NIGMS NIH HHS"],"pagination":["16058-16061"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC7001008"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["140(47)"],"pubmed_abstract":["The antiproliferative antimicrobial fungal metabolites known as the myrocins have been proposed to cross-link DNA by double nucleotide addition. However, the nature of the DNA-reactive species is ambiguous, as myrocins have been isolated as functionally distinct 5-hydroxy-γ-lactone and diosphenol isomers. Based on literature precedent, we hypothesized that the diosphenol 7 (assigned here the trivial name myrocin G) is the biologically active form of the representative isolate (+)-myrocin C (1). To probe this, we developed a short enantioselective route to 7. A powerful fragment-coupling reaction that forms the central ring of the target in 38% yield and in a single step was developed. In support of our hypothesis, 7 was efficiently transformed to the bis(sulfide) 6, a product previously is"],"journal":["Journal of the American Chemical Society"],"pubmed_title":["Synthesis of Myrocin G, the Putative Active Form of the Myrocin Antitumor Antibiotics."],"pmcid":["PMC7001008"],"funding_grant_id":["R35 GM131913","F31 CA213964","T32 GM067543"],"pubmed_authors":["Herzon SB","Economou C","Tomanik M"],"additional_accession":[]},"is_claimable":false,"name":"Synthesis of Myrocin G, the Putative Active Form of the Myrocin Antitumor Antibiotics.","description":"The antiproliferative antimicrobial fungal metabolites known as the myrocins have been proposed to cross-link DNA by double nucleotide addition. However, the nature of the DNA-reactive species is ambiguous, as myrocins have been isolated as functionally distinct 5-hydroxy-γ-lactone and diosphenol isomers. Based on literature precedent, we hypothesized that the diosphenol 7 (assigned here the trivial name myrocin G) is the biologically active form of the representative isolate (+)-myrocin C (1). To probe this, we developed a short enantioselective route to 7. A powerful fragment-coupling reaction that forms the central ring of the target in 38% yield and in a single step was developed. In support of our hypothesis, 7 was efficiently transformed to the bis(sulfide) 6, a product previously is","dates":{"release":"2018-01-01T00:00:00Z","publication":"2018 Nov","modification":"2025-04-19T09:37:55.598Z","creation":"2020-10-29T12:55:09Z"},"accession":"S-EPMC7001008","cross_references":{"pubmed":["30415540"],"doi":["10.1021/jacs.8b10891"]}}