Synthesis of a burkholdine analogue containing β-hydroxytyrosine. Issue 7 (3rd July 2019)

• Record Type: Journal Article
• Authors: Kato, Seiya; Sasaki, Mio; Yano, Shigekazu; Konno, Hiroyuki
• Is Part Of: Bioscience, biotechnology, and biochemistry. Volume 83:Issue 7(2019)
• Page Start: 1216
• Page End: 1219
• Publication Date: 2019-07-03
• Subjects: Antifungal -- lipopeptide -- burkholdine -- β-hydroxytyrosine; Biotechnology -- Periodicals; Biochemistry -- Periodicals; 660.6
• DOI: 10.1080/09168451.2019.1594678
• Languages: English
• ISSNs: 0916-8451

Abstract

ABSTRACT: 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.