Electronic supplementary material
Fig. S1 LC-MS analysis of hydrolysates of QUCHIC (2). LC-UV-PDA chromatogram (a),
TIC (b) and mass chromatograms at m/z 385 (c), 258 (d) and 146 (e) of the reaction mixture
of QUCHIC (2) after acid hydrolysis using the elution program (2). LC-UV-PDA
chromatograms of the authentic QUCHIC (2, f) and authentic 8-quinolinol (g). UV and ESI
mass spectra of peaks 2 (h), hydrolysate-2 (i) and 10 (j). The putative hydrolysis mechanism
of QUCHIC (2) in acidic condition (k)
Fig. S2 GC-MS and LC-MS analyses of product C. TIC (a) and EI mass spectra of the
detected peaks 5 (b) and the authentic APICA N-(5-fluoropentyl) analog (c) obtained by
GC-MS. LC-UV-PDA chromatogram (d) and TIC (e) using the elution program (1) obtained
by LC-MS. UV and ESI mass spectra of peak 5 (f) and the authentic APICA
N-(5-fluoropentyl) analog (g)
Fig. S3 GC-MS and LC-MS analyses of product D. TIC (a) and EI mass spectra of the
detected peaks 6 (b) and the authentic APINACA N-(5-fluoropentyl) analog (c) obtained by
GC-MS. LC-UV-PDA chromatogram (d) and TIC (e) using the elution program (1) obtained
by LC-MS. UV and ESI mass spectra of peak 6 (f) and the authentic APINACA
N-(5-fluoropentyl) analog (g)
Fig. S4 GC-MS and LC-MS analyses of product E. TIC (a) and EI mass spectra of the
detected peaks 7 (b) and the authentic UR-144 N-(5-chloropentyl) analog (c) obtained by
GC-MS. LC-UV-PDA chromatogram (d) and TIC (e) using the elution program (1) obtained
by LC-MS. UV and ESI mass spectra of peak 7 (f) and the authentic UR-144
N-(5-chloropentyl) analog (g)