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Beilstein J. Org. Chem. 2013, 9, 641–646, doi:10.3762/bjoc.9.72
Graphical Abstract
Figure 1: Hypothesised glucuronidation of GHB (1) by UDP-glucuronosyltransferase to give glucuronide 2. UDP =...
Scheme 1: Schmidt glucuronidation [11] with trichloroacetimidate 3. Synthesis of 4 and 5 using acceptors 7 and 8 ...
Scheme 2: Koenigs–Knorr glucuronidation [27] with bromide 10 and acceptors 7 and 8.
Scheme 3: Synthesis of GHB glucuronides 2 and d4-2 by using a Koenigs–Knorr glucuronidation approach. TEMPO: ...
Figure 2: 1H NMR spectrum (D2O, 300 MHz) of GHB glucuronides 2 (top) and d4-2 (bottom). As anticipated, methy...
Figure 3: 1H NMR spectra (500 MHz) of GHB glucuronide 2 in pH 4.8 buffer at t = 0 (rt) and t = 72 h (90 °C) b...