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Beilstein J. Org. Chem. 2019, 15, 2922–2929, doi:10.3762/bjoc.15.286
Graphical Abstract
Figure 1: Chemical structures of naturally occurring argyrins with potent antipseudomonal activity.
Figure 2: The biosynthetic pathway for argyrin production in Cystobacter sp. SBCb004 (Arg1, radical SAM-depen...
Figure 3: Designed mutasynthons 9–14 for argyrin biosynthesis. Peptides are based on three amino acids and ad...
Scheme 1: Synthesis of tripeptide thioesters. Reagents and conditions: (a) SOCl2, EtOH, 78 °C; (b) IBCF, NMM,...
Scheme 2: Improved synthesis of the tripeptide thioester 14. Reagents and conditions: (a) SOCl2, EtOH, 78 °C;...
Figure 4: Analysis of mutasynthon 14 obtained via the convergent synthetic route by HPLC on a HILIC stationar...
Beilstein J. Org. Chem. 2018, 14, 2964–2973, doi:10.3762/bjoc.14.276
Figure 1: N-Acylhomoserine lactones 1 (Z7-C14:1-AHL) and N-acylalanine methyl esters 2 (Z9-C16:1-NAME) occurr...
Figure 2: Total ion chromatogram (TIC) of an XAD extract of Roseovarius sp. D12_1.68. AHLs, NAMEs and related...
Scheme 1: Synthesis of iso-C15:0-NAME (6). DMAP: 4-dimethylaminopyridine, EDC: 1-ethyl-3-(3-dimethylaminoprop...
Figure 3: Mass spectrum of natural compound D, N-(13-methyltetradecanoyl)alanine methyl ester (iso-C15:0-NAME...
Figure 4: Mass spectra of natural compounds a) K (7, C16:0-NABME), b) J (8, C16:1-NABME), and c) N (9, C16:1-...
Scheme 2: Synthesis of N-acylated amino acid methyl esters 7–11. AAME: amino acid methyl ester.
Figure 5: TIC of an XAD extract of Loktanella sp. F14. Compound S is a minor component within the broad peak.
Figure 6: Mass spectra of natural compounds a) R (11, C16:1-NAGME) and b) S (10, C16:0-NAGME).
Figure 7: EI mass spectrometric fragmentation of N-acylated amino acid derivatives. The ions w–z allow identi...
Figure 8: MS2 spectra in ESI positive mode of a) Z9-16OH-C16:1-NAME with [M + H − H2O]+ 356, b) Z9-C16:1-NABM...
Beilstein J. Org. Chem. 2013, 9, 1551–1558, doi:10.3762/bjoc.9.176
Figure 1: The 2-methyl-4(1H)-quinolone compounds: aurachins and endochin.
Scheme 1: Synthesis of aurachin D (4) and geranyl (9), prenyl (10) and methyl (11) analogues.
Scheme 2: Strategy toward the heterocyclic core of aurachin H.
Figure 2: (A) Loss of mitochondrial membrane potential in human U-2 OS osteosarcoma cells that were treated w...