Beilstein J. Org. Chem.2019,15, 1046–1060, doi:10.3762/bjoc.15.102
using a highly diastereoselective hydroboration of C1-exo-methylene pyranosides giving inhibitors with fourfold or better selectivity for galectin-1 over galectin-3, -4C (C-terminal CRD), -4N (N-terminal CRD), -7, -8C, -8N, -9C, and -9N and dissociation constants down to 170 µM.
Keywords: C-galactoside
C-galactoside aglycons, we performed a 200 ns molecular dynamic simulation of 1b in the complex with galectin-1 and galectin-3. Starting conformations were selected with the galactopyranose of 1b positioned overlapping with the positions of the lactose or N-acetyllactosamine galactopyranoses in
galactopyranosyls 1a–n, a majority of which are galectin-1 selective with dissociation constants down to 170 ± 2 µM (1b) and fourfold or better selectivity for galectin-1 over other galectins. This is comparable to or better than known C-galactoside based galectin-1 inhibitors with almost a factor of two [22][23
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Graphical Abstract
Scheme 1:
Diastereoselective hydroboration of glycopyranosyl exomethylene enol ethers 2, 4, and 6: a) BH3-DMS...
Beilstein J. Org. Chem.2015,11, 1392–1397, doi:10.3762/bjoc.11.150
Praha 6, Czech Republic 10.3762/bjoc.11.150 Abstract Cross-metathesis of α- and β-vinyl C-deoxyribosides and α-vinyl C-galactoside with various terminal alkenes under different conditions was studied. The cross-metathesis of the former proceeded with good yields of the corresponding products in
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Graphical Abstract
Scheme 1:
Synthesis of vinyl C-deoxyribosides α-2 and β-2.