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Beilstein J. Org. Chem. 2014, 10, 3073–3086, doi:10.3762/bjoc.10.324
Graphical Abstract
Scheme 1: Synthesis of the alkynyl precursors 3, 6 and 8.
Scheme 2: Synthesis of the mono-(A)- and di-(B)-N-galactopyranosides and lactosides.
Scheme 3: Synthesis of the mono- and di-S-lactosides.
Figure 1: Analysis of 18 as acceptor substrate of TcTS. A: 18 (1 mM) and 3’-sialyllactose (SL, 1 mM), without...
Scheme 4: Sialylation of 18. SL: sialyllactose.
Figure 2: Inhibition of sialylation of LN by compounds 13 and 18. A: N-acetyllactosamine (LN, 1 mM), 3’-sialy...
Figure 3: Comparison of the 1H NMR spectra of 18 (A) and the sialylated derivative 25 (B).