Synthesis of a burkholdine analogue containing β-hydroxytyrosine
| Autor: | Seiya Kato, Shigekazu Yano, Mio Sasaki, Hiroyuki Konno |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Antifungal
Spectrometry Mass Electrospray Ionization Antifungal Agents 010405 organic chemistry medicine.drug_class Chemistry Stereochemistry Organic Chemistry General Medicine 010402 general chemistry 01 natural sciences Applied Microbiology and Biotechnology Biochemistry 0104 chemical sciences Analytical Chemistry Dihydroxyphenylalanine Lipopeptides medicine Molecular Biology Chromatography High Pressure Liquid Biotechnology |
| DOI: | 10.6084/m9.figshare.7901270.v1 |
| Popis: | Synthesis of a β-OHTyr-containing Bk analogue, a cyclic octalipopeptide with antifungal activities, is described. Since β-OHTyr-containing peptides generally are unstable in strong acidic conditions, synthesis of β-HOTyr-containing peptides by SPPS have rarely been reported. To overcome this problem, we found that using distilled TFA removed the protecting groups of side chains of β-OHTyr-containing Bk analogue, which was prepared by Fmoc-SPPS. Abbreviations: β-OHTyr: β-hydroxytyrosine; β-OHAsn: β-hydroxyasparagine; Bk: burkholdine; FAA: fatty acyl amino acid; β-MeOTyr: β-methoxytyrosine; SPPS: solid phase peptide synthesis; MIC: minimun inhibitory concentration; DMF: dimethyl formamide; DIPEA: diisopropylethylamine; DIPC: diisopropylcarbodiimide; HOBt: 1-hydroxybenzotriazole; Fmoc: 9-fluorenylmethyloxycarbonyl; HFIP: 1,1,1,3,3,3-hexafluoropropan-2-ol; TFA: trifluoroacetic acid; LAP: N-lauryl −3-amino-4-carbamolypropanoic acid; HPLC: high performance liquid chromatography; ESI-TOFMS: electrospray ionization-time of flight mass spectrometry; Bn: benzyl; Boc: t-butyloxycatbonyl; 2-CTC: 2-chlorotritylchloride. |
| Databáze: | OpenAIRE |
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