Solid Phase Library Synthesis of Cyclic Depsipeptides: Aurilide and Aurilide Analogues
Autor: | Takayuki Doi, Andrew M. Bray, Takashi Takahashi, Hiroyuki Nagamiya, Peter G. Griffiths |
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Jazyk: | angličtina |
Rok vydání: | 2003 |
Předmět: |
chemistry.chemical_classification
Depsipeptide Magnetic Resonance Spectroscopy Tetrapeptide Chemistry Stereochemistry Peptide General Chemistry Cleavage (embryo) Peptides Cyclic Combinatorial chemistry Gas Chromatography-Mass Spectrometry Anti-Bacterial Agents Peptide Library Phase (matter) Yield (chemistry) Combinatorial Chemistry Techniques Moiety Protecting group Oligopeptides |
Zdroj: | Journal of Combinatorial Chemistry. 5(4):414-428 |
ISSN: | 1520-4766 |
Popis: | A solid-phase combinatorial synthesis approach toward the cyclic depsipeptide aurilide (1) and related analogues is described. The peptide moiety 2 was assembled on trityl linker-functionalized SynPhase Crowns using an Fmoc strategy. Optimization of the tetrapeptide assembly 5 was carried out using parallel multiple synthesis and LC/MS analysis. The aliphatic moiety 3a was coupled with the solid-supported 2 using DIC/HOBt. Following deprotection and cleavage of linear precursor 26, macrocyclization was achieved under high dilution conditions. Removal of the methylthiomethyl protecting group provided aurilide (1) in 11% overall yield. Synthesis of a combinatorial library of aurilide derivatives 4 was accomplished with a similar protocol using the TranSort technique. |
Databáze: | OpenAIRE |
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