{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"omics_type":["Unknown"],"volume":["59(30)"],"submitter":["Grab HA"],"pubmed_abstract":["The first total synthesis of vioprolide D was accomplished in an overall yield of 2.0 % starting from methyl (2S)-3-benzyloxy-2-hydroxypropanoate (16 steps in the longest linear sequence). The cyclic depsipeptide was assembled from two building blocks of similar size and complexity in a modular, highly convergent approach. Peptide bond formation at the C-terminal dehydrobutyrine amino acid of the northern fragment was possible via its (Z)-diastereoisomer. After macrolactamization and formation of the thiazoline ring, the (Z)-double bond of the dehydrobutyrine unit was isomerized to the (E)-double bond of the natural product. The cytotoxicity of vioprolide D is significantly higher than that of its (Z)-diastereoisomer."],"journal":["Angewandte Chemie (International ed. in English)"],"pagination":["12357-12361"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC7383572"],"repository":["biostudies-literature"],"pubmed_title":["Total Synthesis of the Cyclic Depsipeptide Vioprolide D via its (Z)-Diastereoisomer."],"pmcid":["PMC7383572"],"pubmed_authors":["Sieber SA","Kirsch VC","Grab HA","Bach T"],"additional_accession":[]},"is_claimable":false,"name":"Total Synthesis of the Cyclic Depsipeptide Vioprolide D via its (Z)-Diastereoisomer.","description":"The first total synthesis of vioprolide D was accomplished in an overall yield of 2.0 % starting from methyl (2S)-3-benzyloxy-2-hydroxypropanoate (16 steps in the longest linear sequence). The cyclic depsipeptide was assembled from two building blocks of similar size and complexity in a modular, highly convergent approach. Peptide bond formation at the C-terminal dehydrobutyrine amino acid of the northern fragment was possible via its (Z)-diastereoisomer. After macrolactamization and formation of the thiazoline ring, the (Z)-double bond of the dehydrobutyrine unit was isomerized to the (E)-double bond of the natural product. The cytotoxicity of vioprolide D is significantly higher than that of its (Z)-diastereoisomer.","dates":{"release":"2020-01-01T00:00:00Z","publication":"2020 Jul","modification":"2025-04-29T10:52:14.774Z","creation":"2025-04-06T19:41:59.426Z"},"accession":"S-EPMC7383572","cross_references":{"pubmed":["32126146"],"doi":["10.1002/anie.202002328"]}}