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- W1525293089 abstract "(2S,3R) Capreomycidine (‘epicapreomycidine’) are arginine derived non proteinogenic amino acids and can be found as constituents of natural products (e.g. viomycin in the case of capreomycidine and epicapreomycidine in chymostatin respectively). Epicapreomycidine is also a building block of the muraymycins, a family of nucleoside-lipopeptide antibiotics which inhibit an early step in peptidoglycan biosynthesis. For the investigation of structure-activity relationships, which might potentially lead to new antibiotics, a stereocontrolled synthesis of protected epicapreomycidinols and a total synthesis of muraymycin peptide units were established. Thus, valine capreomycidine urea, leucine and 3-hydroxyleucine urea tripeptides were synthesized starting from Garner's aldehyde in an ex-chiral-pool approach. Moreover, a biomimetic approach based on the elucidated biosynthesis of capreomycidine provided access to these amino acids in racemic form. Therefore, starting from 3-azidopropionaldehyde and protected glycine phosphonates protected didehydroornithines were synthesized, which were converted into the racemic amino acids following domino-guanidinylation-aza-michael ring-closure reaction and acidic deprotection. A separation of the isomeric mixture was not successful neither via HPLC nor acylase separation. Starting from the Pbf-protected epicapreomycidinol Fmoc- and Pbf-protected epicapreomycidine was synthesized as a building block for the solid-phase peptide synthesis. Incorporation of this amino acid into model peptides was not successful due to the lack of time. Furthermore, the Pbf-protected epicapreomycidinol was utilized as starting material in the total synthesis of chymostatin B. However, the final reduction step leading to protected chymostatin B did not succeed." @default.
- W1525293089 created "2016-06-24" @default.
- W1525293089 creator A5022471216 @default.
- W1525293089 date "2022-02-20" @default.
- W1525293089 modified "2023-09-26" @default.
- W1525293089 title "Synthese von Capreomycidin- und Epicapreomycidin-haltigen Naturstoff-Bausteinen" @default.
- W1525293089 doi "https://doi.org/10.53846/goediss-2191" @default.
- W1525293089 hasPublicationYear "2022" @default.
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