EC Number   |
Substrates |
Organism |
Products |
Reversibility |
|---|
    2.4.1.133 | more |
enzymatic galactosylation reaction using epimerase UDP-glucose 4-epimerase MgUGE (EC 5.1.3.2) and beta-1,4-galactosyltransferase MgGalT7 with 4-nitrophenol xylose and UDP-glucose as substrates, mass spectrometric analyses of the acceptor substrate and the galactosylated reaction product, coupled assay method, evaluation, overview |
Crassostrea gigas |
? |
- |
- |
| 2.4.1.133 | more |
synthesis of xyloside analogues with substitution of the endocyclic oxygen atom by sulfur or carbon and investigation of them as substrates for beta-1,4-galactosyltransferase 7 (beta4GalT7), overview. The analogues with an endocyclic sulfur atom prove to be excellent substrates for b4GalT7, and are galactosylated approx. fifteen times more efficiently than the corresponding xyloside. The 5a-carba-beta-xylopyranoside in the D-configuration proves to be a good substrate for beta4GalT7, whereas the enantiomer in the L-configuration shows no activity. X-ray crystallography, NMR spectroscopy, and molecular modeling provide a rationale for the pronounced activity of the sulfur analogues. Favorable Pi-Pi interactions between the 2-naphthyl moiety and a tyrosine side chain of the enzyme are observed for the thio analogues (1S,2R,3S,4S)-4-(2-naphthyloxy)cyclohexan-1,2,3-triol, 4-ethyl-6-([(1R,2R,3S,4R)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one, and 4-ethyl-6-([(1S,2S,3R,4S)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one. The carbaxyloside of iliparcil are synthesized as well as its L-xylo-enantiomers 4-ethyl-6-([(1R,2R,3S,4R)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one and 4-ethyl-6-([(1S,2S,3R,4S)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one. The L-xylo-derivative 4-ethyl-6-([(1S,2S,3R,4S)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one shows a much higher antithrombotic activity compared to the D-xylo-enantiomer 4-ethyl-6-([(1R,2R,3S,4R)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one and only the compound with L-xylo conformation functions as substrate for beta4GalT7 when assayed with enzyme extracts from chicken embryo. This is in stark contrast to other investigations where L-enantiomers of xylosides rarely act as substrates for beta4GalT7. Quantum mechanical calculations and docking simulations, overview |
Homo sapiens |
? |
- |
- |
| 2.4.1.133 | UDP-alpha-D-galactose + (1R,2S,3R,4R)-4-(2-naphthyloxy)cyclohexan-1,2,3-triol |
- |
Homo sapiens |
UDP + ? |
- |
? |
| 2.4.1.133 | UDP-alpha-D-galactose + (1S,2R,3S,4S)-4-(2-naphthyloxy)cyclohexan-1,2,3-triol |
- |
Homo sapiens |
UDP + ? |
- |
? |
| 2.4.1.133 | UDP-alpha-D-galactose + 2-naphthyl 1,5-dithio-beta-D-xylopyranoside |
- |
Homo sapiens |
UDP + naphthalen-2-yl 4-O-beta-D-galactopyranosyl-1,5-dithio-beta-D-xylopyranoside |
- |
? |
| 2.4.1.133 | UDP-alpha-D-galactose + 2-naphthyl 5-thio-beta-D-xylopyranoside |
- |
Homo sapiens |
UDP + naphthalen-2-yl 4-O-beta-D-galactopyranosyl-5-thio-beta-D-xylopyranoside |
- |
? |
| 2.4.1.133 | UDP-alpha-D-galactose + 2-naphthyl beta-D-xylopyranoside |
- |
Homo sapiens |
UDP + 4-beta-D-galactosyl-2-naphthyl-beta-D-xylopyranoside |
- |
? |
| 2.4.1.133 | UDP-alpha-D-galactose + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl beta-D-carbaxylopyranoside |
a 5a-carba-beta-xylopyranoside |
Homo sapiens |
UDP + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl 4-O-beta-D-galactopyranosyl-beta-D-carbaxylopyranoside |
- |
? |
| 2.4.1.133 | UDP-alpha-D-galactose + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl beta-L-carbaxylopyranoside |
a 5a-carba-beta-xylopyranoside |
Homo sapiens |
UDP + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl 4-O-beta-D-galactopyranosyl-beta-L-carbaxylopyranoside |
- |
? |
| 2.4.1.133 | UDP-alpha-D-galactose + 4-methylumbelliferyl alpha-D-xylopyranoside |
- |
Homo sapiens |
UDP + 4-methylumbelliferyl 4-O-beta-D-galactopyranosyl-beta-D-xylopyranoside |
- |
? |
