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Beilstein J. Org. Chem. 2019, 15, 299–309, doi:10.3762/bjoc.15.27
Graphical Abstract
Figure 1: FABMS spectrum (positive mode, NBA matrix) of cichorinotoxin over the mass range of m/z 150─1000.
Figure 2: The segment identified based on the FABMS spectrum (peptide fragment b ions).
Figure 3: NMR analyses of the segment consisting of 3-hydroxydecanoyl-dehydrothreonin-proline (600 MHz, aceto...
Figure 4: Key NMR observations used to construct the backbone sequence.
Figure 5: Fragment obtained by acid hydrolysis and each amino acid was exclusively D-configuration (peptide f...
Figure 6: The complete structure of cichorinotoxin monoacetate and the assignments of 1H NMR chemical shifts,...
Figure 7: Determination of the positions of the acetyl groups in the tetraacetate.
Figure 8: Partial structure of compound A as deduced from its NOE data; key NOEs are represented by double-he...
Figure 9: Partial structure of compound B (Val16 to Val22 residues). The chemical shifts (δH and δC (ppm)) ar...
Figure 10: Mechanism of the formation of compounds A and B from cichorinotoxin by alkaline hydrolysis.